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5311 Gulf Of Mexico Drive Unit 5, Longboat Key

Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting. Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath. Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal. Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events. With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.

2 Beds ⋅ 2 Baths ⋅ Mccalls Beach Castle SubDv. ⋅ 34228 Zip Code

Turnkey furnished and positioned just steps from the Gulf’s sandy shoreline, this first-floor residence at Beach Castle on Longboat Key offers a compelling combination of coastal living and proven rental potential. With flexible daily or weekly rental allowances, this two-bedroom retreat presents an exceptional opportunity for personal use, income generation, or both. The light-filled interior features an open layout designed for ease and comfort, where the kitchen, dining, and living areas flow together naturally. Oversized tile flooring, updated impact glass, and sliding doors enhance both durability and livability, while the kitchen is well-appointed with granite countertops, solid wood cabinetry, stainless steel appliances, and built-in shelving—creating a functional space for everyday living or hosting. Floor-to-ceiling sliders lead to a private patio and screened lanai, offering a seamless transition to the outdoors and placing you just moments from the beach. The split-bedroom plan provides added privacy, with the primary suite enjoying direct access to the outdoor space, while the guest bedroom is comfortably sized with its own en-suite bath. Set within the boutique Beach Castle community, residents enjoy a unique beach-to-bay lifestyle with deeded Gulf access, a heated swimming pool and spa, grilling areas, and a fishing pier with day dock on Sarasota Bay. Lush landscaping and well-maintained grounds create a relaxed, resort-style setting that enhances both owner enjoyment and guest appeal. Located on the desirable north end of Longboat Key, this property is just minutes from Bayfront Park, Cedars Tennis Resort, and the island’s scenic biking and walking paths. A short drive south brings you to the Longboat Key Club, St. Armands Circle’s dining and boutiques, and downtown Sarasota’s renowned cultural venues, waterfront parks, and year-round events. With strong rental history, immediate beach access, and a turnkey presentation, this Beach Castle residence offers a rare opportunity to enjoy the best of Longboat Key—whether as an investment, a private getaway, or a combination of both.

5311 Gulf Of Mexico Drive Unit 5, Longboat Key

1065 Gulf Of Mexico Drive Unit 402, Longboat Key

$799,000

This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball courts, fitness center, clubhouse, on-site management, and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota.

2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code

This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball courts, fitness center, clubhouse, on-site management, and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota.

1065 Gulf Of Mexico Drive Unit 402, Longboat Key

2012 Harbourside Drive Unit 2102, Longboat Key

$795,000

Experience the best of Longboat Key living in this spacious 2-bedroom, 2.5-bath condominium located in the gated Fairway Bay community of Bay Isles. Offering approximately 1,590 square feet of living space, this residence features a comfortable two-level layout, a bright Florida room, and an attached garage. Enjoy beautifully landscaped surroundings and an array of community amenities, including a swimming pool, spa, clubhouse, and tennis courts. Conveniently located near Sarasota Bay, local dining, shopping, and the beautiful Gulf beaches, this property offers an exceptional opportunity to enjoy the relaxed coastal lifestyle of Longboat Key. Just a short drive from St. Armands Circle and downtown Sarasota, this residence combines comfort, convenience, and an excellent island location.

2 Beds ⋅ 3 Baths ⋅ Bay Isles SubDv. ⋅ 34228 Zip Code

Experience the best of Longboat Key living in this spacious 2-bedroom, 2.5-bath condominium located in the gated Fairway Bay community of Bay Isles. Offering approximately 1,590 square feet of living space, this residence features a comfortable two-level layout, a bright Florida room, and an attached garage. Enjoy beautifully landscaped surroundings and an array of community amenities, including a swimming pool, spa, clubhouse, and tennis courts. Conveniently located near Sarasota Bay, local dining, shopping, and the beautiful Gulf beaches, this property offers an exceptional opportunity to enjoy the relaxed coastal lifestyle of Longboat Key. Just a short drive from St. Armands Circle and downtown Sarasota, this residence combines comfort, convenience, and an excellent island location.

2012 Harbourside Drive Unit 2102, Longboat Key

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key

$795,000

Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door. Recently renovated from top to bottom and offered FURNISHED, this residence is ready to enjoy from day one. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. Other thoughtful updates throughout include luxury vinyl flooring throughout, fresh carpeting in the bedrooms, beautifully remodeled, IMPACT WINDOWS, generous storage, and the convenience of an in-unit washer and dryer. Located in the pet-friendly waterfront community of Windward Bay, residents enjoy an impressive collection of amenities including boat slips, two swimming pools, a fitness center, sauna, tennis and pickleball courts, and three beach access points. NO upcoming special assessments, FULLY FUNDED reserves, and a PASSED Milestone. Perfectly positioned on Longboat Key, this penthouse offers the relaxed island lifestyle while keeping you conveniently connected to the dining, shopping, beaches, and entertainment of Longboat Key, St Armands, and Anna Maria Island. Whether you're searching for a full-time residence or your own Florida getaway, this turnkey waterfront penthouse is ready to welcome you home.

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code

Welcome to your Longboat Key PENTHOUSE, where unobstructed PANORAMIC WATER VIEWS from every room create a breathtaking backdrop from the moment you walk through the door. Recently renovated from top to bottom and offered FURNISHED, this residence is ready to enjoy from day one. The BRAND-NEW KITCHEN showcases quartz countertops, custom cabinetry, and all-new stainless-steel appliances, opening seamlessly to the bright and airy living space. Both bathrooms have been completely updated with modern finishes and quartz countertops, creating a fresh, cohesive feel throughout the home. Other thoughtful updates throughout include luxury vinyl flooring throughout, fresh carpeting in the bedrooms, beautifully remodeled, IMPACT WINDOWS, generous storage, and the convenience of an in-unit washer and dryer. Located in the pet-friendly waterfront community of Windward Bay, residents enjoy an impressive collection of amenities including boat slips, two swimming pools, a fitness center, sauna, tennis and pickleball courts, and three beach access points. NO upcoming special assessments, FULLY FUNDED reserves, and a PASSED Milestone. Perfectly positioned on Longboat Key, this penthouse offers the relaxed island lifestyle while keeping you conveniently connected to the dining, shopping, beaches, and entertainment of Longboat Key, St Armands, and Anna Maria Island. Whether you're searching for a full-time residence or your own Florida getaway, this turnkey waterfront penthouse is ready to welcome you home.

4800 Gulf Of Mexico Drive Unit PH 3, Longboat Key

5655 Gulf Of Mexico Drive Unit A107, Longboat Key

$775,000

Enjoy Gulf-front living and gorgeous water views in this move-in-ready, two-bedroom, two-bath waterfront condominium, ideally in an elevated community near the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the ideal place to live. This location is within proximity to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, barbecue area, bike racks and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while offering flexibility to enjoy your beach getaway. There is a lockable owner's closet in the unit. You have to see this home to really appreciate how special it is.

2 Beds ⋅ 2 Baths ⋅ Cedars West Of Longboat Inc SubDv. ⋅ 34228 Zip Code

Enjoy Gulf-front living and gorgeous water views in this move-in-ready, two-bedroom, two-bath waterfront condominium, ideally in an elevated community near the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the ideal place to live. This location is within proximity to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, barbecue area, bike racks and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while offering flexibility to enjoy your beach getaway. There is a lockable owner's closet in the unit. You have to see this home to really appreciate how special it is.

5655 Gulf Of Mexico Drive Unit A107, Longboat Key

1955 Gulf Of Mexico Drive Unit G6-407, Longboat Key

$769,000

Gulf-front view in Seaplace with reserved covered parking! This is a special opportunity to own a rarely available floor plan on the penthouse level in an atrium-style building. This residence has extra-high ceilings and spectacular Gulf water views, a large screened-in lanai overlooking the Gulf, and an extra-spacious open floor plan. It's being sold turnkey furnished and is ready to enjoy from day one. The open living and dining areas flow seamlessly to the expansive screened-in lanai, creating the perfect setting to relax, entertain, and take in the stunning Gulf sunsets. The generous primary bedroom offers an abundance of closet storage, while an in-unit washer and dryer provide everyday convenience. Additional features include a new impact-rated front door with a digital lock system, impact window and door shutters, and a private locking storage unit conveniently located on the same floor. The reserved covered parking space is very convenient to the elevator. HVAC, 2025. Set on 42 acres of Gulf-front, meticulously landscaped grounds, Seaplace offers resort-style amenities that make this community especially inviting. There are 2 large swimming pools with spas and a separate kiddie pool that provide plenty of options for relaxing and enjoying the Florida sunshine. At the beach, lounges and umbrellas are set up for residents to enjoy, making a day by the Gulf effortless. There are 3 har-tru tennis courts, and a mile of walking trails on the property. The modern clubhouse offers a state-of-the-art gym and an inviting gathering room where residents come together for parties, card games, social activities, or simply to get to know their neighbors. A special lending library adds another thoughtful touch. As the sun begins to set, residents gather around the clubhouse firepit to socialize, grill dinner, and watch the spectacular sunsets together over the Gulf. Seaplace is just a short 5 minute drive to St. Armand's Circle, where you'll find fantastic shopping and incredible restaurants and cafes. Also, at Seaplace you'll have the convenience of being close to Publix and CVS on Longboat Key which are within walking or biking riding distance or minutes away by car. Visit this residence in Seaplace to see how wonderful Longboat Key life can truly be. Book your appointment today.

2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv. ⋅ 34228 Zip Code

Gulf-front view in Seaplace with reserved covered parking! This is a special opportunity to own a rarely available floor plan on the penthouse level in an atrium-style building. This residence has extra-high ceilings and spectacular Gulf water views, a large screened-in lanai overlooking the Gulf, and an extra-spacious open floor plan. It's being sold turnkey furnished and is ready to enjoy from day one. The open living and dining areas flow seamlessly to the expansive screened-in lanai, creating the perfect setting to relax, entertain, and take in the stunning Gulf sunsets. The generous primary bedroom offers an abundance of closet storage, while an in-unit washer and dryer provide everyday convenience. Additional features include a new impact-rated front door with a digital lock system, impact window and door shutters, and a private locking storage unit conveniently located on the same floor. The reserved covered parking space is very convenient to the elevator. HVAC, 2025. Set on 42 acres of Gulf-front, meticulously landscaped grounds, Seaplace offers resort-style amenities that make this community especially inviting. There are 2 large swimming pools with spas and a separate kiddie pool that provide plenty of options for relaxing and enjoying the Florida sunshine. At the beach, lounges and umbrellas are set up for residents to enjoy, making a day by the Gulf effortless. There are 3 har-tru tennis courts, and a mile of walking trails on the property. The modern clubhouse offers a state-of-the-art gym and an inviting gathering room where residents come together for parties, card games, social activities, or simply to get to know their neighbors. A special lending library adds another thoughtful touch. As the sun begins to set, residents gather around the clubhouse firepit to socialize, grill dinner, and watch the spectacular sunsets together over the Gulf. Seaplace is just a short 5 minute drive to St. Armand's Circle, where you'll find fantastic shopping and incredible restaurants and cafes. Also, at Seaplace you'll have the convenience of being close to Publix and CVS on Longboat Key which are within walking or biking riding distance or minutes away by car. Visit this residence in Seaplace to see how wonderful Longboat Key life can truly be. Book your appointment today.

1955 Gulf Of Mexico Drive Unit G6-407, Longboat Key

1926 Harbourside Drive Unit 1302, Longboat Key

$769,000

GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.

2 Beds ⋅ 3 Baths ⋅ Fairway Bay 1 SubDv. ⋅ 34228 Zip Code

GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.

1926 Harbourside Drive Unit 1302, Longboat Key

4800 Gulf Of Mexico Drive Unit 205, Longboat Key

$759,000

STOP THE CAR...THIS IS THE ONE! Perfectly positioned to capture breathtaking Sarasota Bay views, this spectacularly renovated coastal retreat offers a rare combination of luxury, comfort, and natural beauty in one of Longboat Key's most sought-after waterfront communities. Showcasing exceptional craftsmanship and designer-curated finishes throughout, this stunning two-bedroom residence with an additional Queen Murphy Bed guest accommodation and guest closet has been thoughtfully reimagined to create a truly move-in-ready and turnkey masterpiece. Recent enhancements include brand-new luxury vinyl plank flooring and newly installed electric window blinds, adding both style and convenience to this exceptional home. From the moment you step inside, you'll be captivated by shimmering water views and the seamless blend of elegant interiors and the beauty of the outdoors. The open-concept floor plan is designed for effortless living and entertaining, creating a warm and inviting atmosphere filled with natural light. At the heart of the home, the chef-inspired gourmet kitchen is a showstopper, featuring a spacious granite island, abundant cabinetry, premium finishes, and a welcoming dining area perfect for gathering with family and friends (Dining for 6). The living room and Florida room serve as front-row seats to some of the most spectacular scenery on Sarasota Bay with an additional formal dining area for 6. Watch playful dolphins glide through the water, spot gentle manatees just offshore, and enjoy the daily parade of coastal birds from your elevated vantage point. Whether savoring a peaceful sunrise with your morning coffee or unwinding beneath moonlit skies reflected across the bay, every day feels like a vacation. The primary suite is a private sanctuary designed for relaxation and renewal. This luxurious retreat features a cozy fireplace, beautifully crafted custom walk-in closet, and an ensuite bath showcasing lavish finishes and thoughtful design. “Pet Friendly” Windward Bay is a low-density residence and magical wildlife haven nestled mid Longboat Key, flourishing on 26 acres and graced with 1/2 a mile of waterfront trails for your enjoyment. Unparalleled resort-like amenities include 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee (waitlist), kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits/barbecues throughout the property. Steps away from the tranquil Gulf of Mexico with one deeded beach access and two public beach accesses directly across the street. For those seeking outdoor adventure, this property offers direct access to the water, making it perfect for boating, fishing, or simply enjoying a day on the water. Beyond the community, enjoy easy access to St. Armands Circle, Downtown Sarasota, Bridge Street, Historic Cortez Fishing Village, championship golf courses, world-class dining, boutique shopping, and Sarasota's renowned arts and cultural attractions. Rarely does a residence combine this level of design, comfort, location, and lifestyle. Come discover why this exceptional Windward Bay home is one of the finest offerings ever in the community. STOP THE CAR and schedule your private showing today.

2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

STOP THE CAR...THIS IS THE ONE! Perfectly positioned to capture breathtaking Sarasota Bay views, this spectacularly renovated coastal retreat offers a rare combination of luxury, comfort, and natural beauty in one of Longboat Key's most sought-after waterfront communities. Showcasing exceptional craftsmanship and designer-curated finishes throughout, this stunning two-bedroom residence with an additional Queen Murphy Bed guest accommodation and guest closet has been thoughtfully reimagined to create a truly move-in-ready and turnkey masterpiece. Recent enhancements include brand-new luxury vinyl plank flooring and newly installed electric window blinds, adding both style and convenience to this exceptional home. From the moment you step inside, you'll be captivated by shimmering water views and the seamless blend of elegant interiors and the beauty of the outdoors. The open-concept floor plan is designed for effortless living and entertaining, creating a warm and inviting atmosphere filled with natural light. At the heart of the home, the chef-inspired gourmet kitchen is a showstopper, featuring a spacious granite island, abundant cabinetry, premium finishes, and a welcoming dining area perfect for gathering with family and friends (Dining for 6). The living room and Florida room serve as front-row seats to some of the most spectacular scenery on Sarasota Bay with an additional formal dining area for 6. Watch playful dolphins glide through the water, spot gentle manatees just offshore, and enjoy the daily parade of coastal birds from your elevated vantage point. Whether savoring a peaceful sunrise with your morning coffee or unwinding beneath moonlit skies reflected across the bay, every day feels like a vacation. The primary suite is a private sanctuary designed for relaxation and renewal. This luxurious retreat features a cozy fireplace, beautifully crafted custom walk-in closet, and an ensuite bath showcasing lavish finishes and thoughtful design. “Pet Friendly” Windward Bay is a low-density residence and magical wildlife haven nestled mid Longboat Key, flourishing on 26 acres and graced with 1/2 a mile of waterfront trails for your enjoyment. Unparalleled resort-like amenities include 2 tennis/pickleball courts, 2 marinas with 28 boat & jet ski slips for a low monthly fee (waitlist), kayak racks, 2 heated pools, shuffleboard, bike racks, a clubhouse with kitchen, library, fitness room, meeting room, 2 saunas, and community fire pits/barbecues throughout the property. Steps away from the tranquil Gulf of Mexico with one deeded beach access and two public beach accesses directly across the street. For those seeking outdoor adventure, this property offers direct access to the water, making it perfect for boating, fishing, or simply enjoying a day on the water. Beyond the community, enjoy easy access to St. Armands Circle, Downtown Sarasota, Bridge Street, Historic Cortez Fishing Village, championship golf courses, world-class dining, boutique shopping, and Sarasota's renowned arts and cultural attractions. Rarely does a residence combine this level of design, comfort, location, and lifestyle. Come discover why this exceptional Windward Bay home is one of the finest offerings ever in the community. STOP THE CAR and schedule your private showing today.

4800 Gulf Of Mexico Drive Unit 205, Longboat Key

5270 Gulf Of Mexico Drive Unit 508, Longboat Key

$754,900

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

3 Beds ⋅ 3 Baths ⋅ The Banyan Bay Club SubDv. ⋅ 34228 Zip Code

Rarely available and beautifully positioned, this 3-bedroom, 3-bath fully furnished residence with UNOBSTRUCTED FULL BAY VIEWS invites you to experience true beach-to-bay living in the coveted community of Banyan Bay on the north end of Longboat Key. From sunrise coffees on your private terrace to evenings spent watching dolphins glide across the bay, this home offers an effortless blend of comfort, coastal elegance, and unforgettable daily moments. Set within an intimate community of just 26 Bayside and 18 Gulf side residences, Banyan Bay provides a peaceful retreat with exceptional amenities. Start your mornings with a stroll along your private Gulf beach access, join neighbors for a friendly match on the tennis/pickleball court, launch a kayak directly onto the bay, or unwind by the heated pool after a day on the water. A day dock/fishing pier, fitness center, clubhouse, and convenient bicycle storage further enhance the lifestyle of this warm, social community. Inside, more than 1,400 square feet of thoughtfully designed living space showcases a spacious kitchen with granite countertops, SS appliances, and a breakfast bar and nook ideal for casual dining or gathering with friends. The open great-room layout features soaring ceilings that fill the home with natural light and frame the captivating bayfront scenery. The primary suite offers its own private terrace overlooking the shimmering water—perfect for quiet mornings or evening breezes. A guest suite on the main level ensures comfort and privacy, while a charming spiral staircase leads to a versatile loft and a spacious third bedroom suite—ideal for hosting visitors, working remotely, or enjoying a dedicated creative space. Terra cotta tile flooring throughout the first level brings warmth and coastal character, while Tommy Bahama inspired finishes make this turnkey furnished residence with a NEW AC (Aug 2026) truly move-in-ready. Beyond the community, you’ll find yourself within walking-distance to restaurants and the Centre Shops. Durante Park and the Longboat Key Center for the Arts are just moments away, adding convenience and charm to the neighborhood. Discover the rare combination of lifestyle, location, and waterfront living that only Banyan Bay can offer—where every day feels like a coastal escape.

5270 Gulf Of Mexico Drive Unit 508, Longboat Key

$750,000

This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

This must-see hidden gem on the north end of Longboat Key offers a quintessential Florida lifestyle. Waterview’s galore as you walk into your newly completed, renovated Florida paradise home, on a deepwater marina and canal, which epitomizes beauty and style. Boat lovers will want the location of this totally turnkey furnished 1,423-square-foot standalone two-bedroom, two-bath home, with your upgraded composite boat dock just 15 feet behind your villa. Completely remodeled, this home provides contemporary classic design features that create an open airy gorgeous living space. All new stainless appliances in 2026, air-conditioner 2025, roof 2019 and more. The open kitchen design with a large island, new quartz countertops, plenty of beautiful new cabinets with roll-out drawers and a contrasting white and gray classic color scheme. Great counter space makes the kitchen ideal for entertaining and enjoying the coastal casual lifestyle. Beautiful porcelain tile flows throughout the home, providing continuity from room to room. An oversized skylight in the great room with retractable shade provides lots of extra natural brightness. The large primary bedroom is complete with a fully refashioned en-suite bath with gorgeous granite countertops and custom-tiled shower. A spacious walk-in closet provides plenty of room for your coastal style wardrobe. The second bath mimics the maintained class and elegance of this home with granite counters and tiled shower. The lanai has been transformed into extra living space with a cozy study and separate office nook. The study is an ideal spot to curl up with a book or just sit privately and watch the beautiful white pelicans float by with dolphins and manatees alongside. This flexplace can also house extra sleepover guests. The double lanai facing the water allows a panoramic view and full access to your large, elevated brick paver patio and dock from floor-to-ceiling, impact-grade patio doors. Go outside to a private oasis that overlooks the wide-open canal, marina and bay views. Sit, dine, entertain or sunbathe while you enjoy the abundant wildlife from the comfort of your patio paradise, or hop in your boat secured to your 5-by-25-foot dock and head out to one of the many Longboat Key restaurants. Some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico. Impact windows and new hurricane-rated doors throughout. The Spanish Main maintenance-free community has a wonderful neighborhood feel with heated pool, deeded beach access, a 40-foot slip marina with social events galore, making every day feel like a vacation as you lounge in the sun poolside and enjoy the sea The deeded beach access is ideal for those numerous beach days and magnificent sunsets. Pet-friendly, maintenance-free, and an active 55-plus community are added benefits for your enjoyment. Only a short drive to fantastic shops and restaurants, including Anna Maria Island, plus cultural events Sarasota and St. Armands Circle have to offer. This villa has been fully renovated in compliance with FEMA standards due to hurricane flooding in 2024.

900 Spanish Drive N, Longboat Key

$750,000

PRICE IMPROVEMENT!! Canal-front 3-bedroom, 2-bath home with an attached 1-bedroom, 1-bath apartment above the garage with private entrance, offering 2,242 square feet of total living space. The property has completed remediation and is ready to be rebuilt to suit your needs. Features include high ceilings, a 2-car garage, and a generous ¼-acre lot. Canal offers direct access to Sarasota Bay with no bridges. Conveniently located minutes from marinas, dining, and shopping, with easy access to St. Armands Circle, downtown Sarasota, and Anna Maria Island. Bring your personal touch to recreate this gem or start new and build the home you've always wanted on this 124 ft wide lot. A property with exceptional location and potential.

4 Beds ⋅ 3 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

PRICE IMPROVEMENT!! Canal-front 3-bedroom, 2-bath home with an attached 1-bedroom, 1-bath apartment above the garage with private entrance, offering 2,242 square feet of total living space. The property has completed remediation and is ready to be rebuilt to suit your needs. Features include high ceilings, a 2-car garage, and a generous ¼-acre lot. Canal offers direct access to Sarasota Bay with no bridges. Conveniently located minutes from marinas, dining, and shopping, with easy access to St. Armands Circle, downtown Sarasota, and Anna Maria Island. Bring your personal touch to recreate this gem or start new and build the home you've always wanted on this 124 ft wide lot. A property with exceptional location and potential.

651 Jungle Queen Way, Longboat Key

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

$725,000

Turnkey furnished, beautifully updated with beachfront resort amenities! Enjoy easy first-floor access at desirable Club Longboat Beach & Tennis Resort. This tastefully appointed, light and bright residence offers approximately 1,484 square feet, three bedrooms and two baths, with no elevators or long walks. Enjoy covered parking conveniently at your doorstep. Wide-plank flooring and a coastal palette complement the updated kitchen with white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash, and a large island with seating. Floor-to-ceiling sliders open from each room onto lushly landscaped paver walkways and a large private patio. The primary suite features patio access, generous closets and an updated bath with a walk-in shower. A den/third bedroom with a Murphy bed and large closet adds flexibility for guests. Abundant interior storage, a large laundry room with a full-size washer and dryer and additional cabinetry, a private exterior storage room and one covered parking space complete the offering. Enjoy approximately 750 feet of Gulf-front beach, beach chairs and umbrellas, eight Har-Tru tennis courts, an on-site tennis professional, pickleball, two heated pools with separate adult and family areas, spa, sauna, grilling, bocce and fishing. On-site management and an active social calendar enhance the community experience. A newly renovated clubhouse with expanded fitness and social spaces is planned. Club Longboat is pet-friendly for owners, including those with large dogs, and allows a 30-day minimum rental period and up to 12 leases annually. Rental history is available upon request. This mid-key location offers convenient access to dining, boating and golf, with St. Armands Circle and downtown Sarasota a short drive away. Arrive, unpack and head to the beach!

3 Beds ⋅ 2 Baths ⋅ Club Longboat Beach & Tennis SubDv. ⋅ 34228 Zip Code

Turnkey furnished, beautifully updated with beachfront resort amenities! Enjoy easy first-floor access at desirable Club Longboat Beach & Tennis Resort. This tastefully appointed, light and bright residence offers approximately 1,484 square feet, three bedrooms and two baths, with no elevators or long walks. Enjoy covered parking conveniently at your doorstep. Wide-plank flooring and a coastal palette complement the updated kitchen with white cabinetry, stainless steel appliances, under-cabinet lighting, a glass tile backsplash, and a large island with seating. Floor-to-ceiling sliders open from each room onto lushly landscaped paver walkways and a large private patio. The primary suite features patio access, generous closets and an updated bath with a walk-in shower. A den/third bedroom with a Murphy bed and large closet adds flexibility for guests. Abundant interior storage, a large laundry room with a full-size washer and dryer and additional cabinetry, a private exterior storage room and one covered parking space complete the offering. Enjoy approximately 750 feet of Gulf-front beach, beach chairs and umbrellas, eight Har-Tru tennis courts, an on-site tennis professional, pickleball, two heated pools with separate adult and family areas, spa, sauna, grilling, bocce and fishing. On-site management and an active social calendar enhance the community experience. A newly renovated clubhouse with expanded fitness and social spaces is planned. Club Longboat is pet-friendly for owners, including those with large dogs, and allows a 30-day minimum rental period and up to 12 leases annually. Rental history is available upon request. This mid-key location offers convenient access to dining, boating and golf, with St. Armands Circle and downtown Sarasota a short drive away. Arrive, unpack and head to the beach!

5055 Gulf Of Mexico Drive Unit 115, Longboat Key

448 Gulf Of Mexico Drive Unit A104, Longboat Key

$725,000

Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat slip! Longboat Key is the place you want to be for the quiet solitude of a gulf front key condo with easy access to the culture and services of Sarasota! This two bedroom, two bathroom Condo in the bay side community of Bay Harbour, has its own private marina with no wait list, and is just one bridge to the Gulf! Beach access is within minutes from several locations on Longboat, Lido and Anna Maria Island. With a Base Flood Elevation of 10 Ft, this unit was High and Dry during the storms of 2024. It has been exquisitely redesigned with upscale quartz and Cambria counter tops, ceramic and porcelain tile flooring and Bosch Appliances. There is plenty of storage available with the pantry and built in closets. The separate pantry has a washer and dryer. Bay Harbour is a South Longboat Key community of 39 units in two buildings with a private pool, easily accessible pool baths, community room and fitness center. Each unit has assigned carport parking and separate locked storage. A well-managed and well-maintained community with reserves; the condo fees are among the lowest on the gulf at just $1,040 per month!

2 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code

Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat slip! Longboat Key is the place you want to be for the quiet solitude of a gulf front key condo with easy access to the culture and services of Sarasota! This two bedroom, two bathroom Condo in the bay side community of Bay Harbour, has its own private marina with no wait list, and is just one bridge to the Gulf! Beach access is within minutes from several locations on Longboat, Lido and Anna Maria Island. With a Base Flood Elevation of 10 Ft, this unit was High and Dry during the storms of 2024. It has been exquisitely redesigned with upscale quartz and Cambria counter tops, ceramic and porcelain tile flooring and Bosch Appliances. There is plenty of storage available with the pantry and built in closets. The separate pantry has a washer and dryer. Bay Harbour is a South Longboat Key community of 39 units in two buildings with a private pool, easily accessible pool baths, community room and fitness center. Each unit has assigned carport parking and separate locked storage. A well-managed and well-maintained community with reserves; the condo fees are among the lowest on the gulf at just $1,040 per month!

448 Gulf Of Mexico Drive Unit A104, Longboat Key

2020 Harbourside Drive Unit 442, Longboat Key

$699,000

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Enjoy direct Sarasota Bay views and deeded private beach access from this updated fourth-floor residence in Fairway Bay, an established gated Bay Isles community within the Longboat Key Club setting. Residence #442 at 2020 Harbourside Drive offers 1,312 square feet of bright, airy living space with two bedrooms and two bathrooms—an inviting coastal retreat where the bay becomes part of everyday life. Floor-to-ceiling views from the kitchen, dining area, and living room create a memorable backdrop for daily living and entertaining, while the private balcony is an ideal place to begin the day with a Sarasota Bay sunrise or settle in for the evening as the sky changes over the water. Keep watch for passing boats, coastal birds, and the occasional manatee in the bay below. The residence has been thoughtfully updated with a kitchen featuring granite countertops, a granite breakfast bar, stainless-steel appliances, and a newer microwave. A front-loading LG washer and dryer are included for everyday convenience. Ceramic tile flooring extends throughout the main living areas and guest spaces, while the primary bedroom features warm wood flooring. Fairway Bay offers a resort-inspired waterfront lifestyle with scenic walking paths, a heated swimming pool and spa, fitness facilities, social spaces, tennis courts, and paddle sports. Beyond the bayfront setting, owners enjoy deeded access to the Bay Isles Beach Club, providing a private connection to Longboat Key’s renowned Gulf beaches. It is the best of both waterfront worlds: tranquil Sarasota Bay just outside your door and the Gulf of Mexico’s white-sand shoreline close by. The community’s central island location makes it easy to walk or bike to nearby conveniences, including grocery shopping, pharmacy services, and tennis. For those who wish to expand their recreational options, membership opportunities may be available through the nearby Longboat Key Club, with its golf, tennis, dining, fitness, spa, and full-service deep-water marina amenities. St. Armands Circle is moments away for boutique shopping and acclaimed dining, while downtown Sarasota offers a vibrant extension of the island lifestyle with arts, culture, restaurants, and waterfront attractions. This is a rare opportunity to enjoy a beautifully updated fourth-floor bayfront residence where views, private beach access, resort-style amenities, and the effortless rhythm of Longboat Key living come together.

2020 Harbourside Drive Unit 442, Longboat Key

$699,000

This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.

2 Beds ⋅ 3 Baths ⋅ Northgate Of Longboat Key SubDv. ⋅ 34228 Zip Code

This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.

490 N Shore Road Unit 6, Longboat Key

$695,000

Due to a change with the buyer, this stunning property is back on the market and available for immediate showings. Everything is prepped, cleaned and ready for the new owner. Inspections, survey, flood elevation, appraisal, wind mitigation, title work and 4-point inspection are all performed, passed and ready to go. A simple change in the buyer's lifestyle created your next opportunity. If you or your client missed this the first time, Now is the perfect time. Let’s get you in for a private tour before it’s gone again! On site you will discover this stunning, fully renovated Cali-Modern residence, where coastal design meets the tranquil elegance of Longboat Key. Sophisticated and move-in ready, this home offers an effortless lifestyle on the highly sought-after North End of the island. From the moment you step inside, you are greeted by clean, modern lines, vaulted ceilings, and beautiful stone tile floors, all bathed in gorgeous natural light. The home has been lovingly and extensively renovated, featuring a sparkling upgraded kitchen and bathrooms, new appliances, and premium finishes in every corner. Step outside to your private, fully fenced backyard oasis—the perfect spot for sunset cocktails and spacious enough to accommodate a future pool. The location is truly unbeatable. You are steps from both Gulf and Bay access and within walking distance of island favorites like Harry's Deli, The Continental Kitchen, Euphemia Haye, and Cedars East Tennis & Fitness Resort. With excellent rental potential projected at $13,000 per month in season, this property is a powerful income generator. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, a natural gem filled with walking trails, fishing piers, and kayak launches. With a standing seam metal roof, Hardi board siding, newer double-pane windows, and offered fully furnished, this charmer is truly turnkey. Don't wait—come experience the magic of island life for yourself!

3 Beds ⋅ 3 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Due to a change with the buyer, this stunning property is back on the market and available for immediate showings. Everything is prepped, cleaned and ready for the new owner. Inspections, survey, flood elevation, appraisal, wind mitigation, title work and 4-point inspection are all performed, passed and ready to go. A simple change in the buyer's lifestyle created your next opportunity. If you or your client missed this the first time, Now is the perfect time. Let’s get you in for a private tour before it’s gone again! On site you will discover this stunning, fully renovated Cali-Modern residence, where coastal design meets the tranquil elegance of Longboat Key. Sophisticated and move-in ready, this home offers an effortless lifestyle on the highly sought-after North End of the island. From the moment you step inside, you are greeted by clean, modern lines, vaulted ceilings, and beautiful stone tile floors, all bathed in gorgeous natural light. The home has been lovingly and extensively renovated, featuring a sparkling upgraded kitchen and bathrooms, new appliances, and premium finishes in every corner. Step outside to your private, fully fenced backyard oasis—the perfect spot for sunset cocktails and spacious enough to accommodate a future pool. The location is truly unbeatable. You are steps from both Gulf and Bay access and within walking distance of island favorites like Harry's Deli, The Continental Kitchen, Euphemia Haye, and Cedars East Tennis & Fitness Resort. With excellent rental potential projected at $13,000 per month in season, this property is a powerful income generator. The best-kept secret? A private back gate leads you directly into the 32 acres of Joan Durante Park, a natural gem filled with walking trails, fishing piers, and kayak launches. With a standing seam metal roof, Hardi board siding, newer double-pane windows, and offered fully furnished, this charmer is truly turnkey. Don't wait—come experience the magic of island life for yourself!

624 Saint Judes Drive, Longboat Key

5310 Gulf Of Mexico Drive Unit 16, Longboat Key

$689,000

Turnkey-Furnished Longboat Key Condo with Dock Access & Rental Potential. Discover effortless coastal living in this beautifully furnished turnkey condo on desirable Longboat Key. Enjoy rare short-term rental flexibility, a bright and stylish interior, and immediate move-in or income potential. Relax by the waterfront dock that is perfect for sunsets and kayaking. Enjoy close access to Gulf beaches, dining, shopping, and island amenities. An ideal Longboat Key vacation retreat or rental investment.

2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code

Turnkey-Furnished Longboat Key Condo with Dock Access & Rental Potential. Discover effortless coastal living in this beautifully furnished turnkey condo on desirable Longboat Key. Enjoy rare short-term rental flexibility, a bright and stylish interior, and immediate move-in or income potential. Relax by the waterfront dock that is perfect for sunsets and kayaking. Enjoy close access to Gulf beaches, dining, shopping, and island amenities. An ideal Longboat Key vacation retreat or rental investment.

5310 Gulf Of Mexico Drive Unit 16, Longboat Key

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

$678,901

Virtually Staged. Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #402, LONGBOAT KEY, FL. This is a 2 Bedroom, 2 Bathroom Condominium with stunning views of the brilliant Gulf from every room and immediate beach access on Longboat Key. Arbomar Owners enjoy a heated beachfront pool, fitness center, and a welcoming well-maintained community with private coded access and an elevator. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways with diamond coating, Brand New carports within the past year and new doors and impact-rated windows throughout the community. The pool has just been resurfaced and has a brand new pump and heater. Inside, the home is ready for you to add your own flair. Ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. This condo has a community washer and dryer just outside the front door, and also has a space where one could be installed inside. There are also storm shutters on the balcony for extra security. It comes with one dedicated covered parking spot and extra storage space downstairs. The amenities includes 24 hour security, pavered parking and entrance, elevators, a glistening resort style swimming pool, recreation clubhouse, shuffleboard, and fitness center. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions and world-class golf, and just a short trip to the Sarasota International Airport. Experience the luxury of Florida living with panoramic Gulf views and stunning sunsets every day. This building has cell phone towers on the roof that generate significant income for the association. With low maintenance fees and a great rental policy. The Milestone study and SIRS are completed and any past fees will be brought up to date at closing. This sale will come with a Warranty Deed ensuring that all taxes and condominium fees are current. This property will only be sold at Auction. ANY price in any listing or advertisement is for reference only, the selling price will be determined at auction. There is NO starting bid, you may bid any amount.

2 Beds ⋅ 2 Baths ⋅ Arbomar Apts SubDv. ⋅ 34228 Zip Code

Virtually Staged. Auction Property. Auction Property. This Beachfront Condominium will be sold at an Online Auction October 29 ~ November 4. 4485 GULF OF MEXICO DR, #402, LONGBOAT KEY, FL. This is a 2 Bedroom, 2 Bathroom Condominium with stunning views of the brilliant Gulf from every room and immediate beach access on Longboat Key. Arbomar Owners enjoy a heated beachfront pool, fitness center, and a welcoming well-maintained community with private coded access and an elevator. All special assessments will be paid in full by the seller at closing, eliminating future capital expense concerns for the buyer. The residence features a bright, open layout designed to capture stunning water views and coastal breezes. Significant recent improvements provide exceptional value and peace of mind, including a new roof, new balconies and walkways with diamond coating, Brand New carports within the past year and new doors and impact-rated windows throughout the community. The pool has just been resurfaced and has a brand new pump and heater. Inside, the home is ready for you to add your own flair. Ideal for full-time living, a seasonal retreat, or an income-producing beach getaway. This condo has a community washer and dryer just outside the front door, and also has a space where one could be installed inside. There are also storm shutters on the balcony for extra security. It comes with one dedicated covered parking spot and extra storage space downstairs. The amenities includes 24 hour security, pavered parking and entrance, elevators, a glistening resort style swimming pool, recreation clubhouse, shuffleboard, and fitness center. Perfectly positioned on Longboat Key, Arbomar is just minutes from St. Armands Circle, Sarasota’s dining and cultural attractions and world-class golf, and just a short trip to the Sarasota International Airport. Experience the luxury of Florida living with panoramic Gulf views and stunning sunsets every day. This building has cell phone towers on the roof that generate significant income for the association. With low maintenance fees and a great rental policy. The Milestone study and SIRS are completed and any past fees will be brought up to date at closing. This sale will come with a Warranty Deed ensuring that all taxes and condominium fees are current. This property will only be sold at Auction. ANY price in any listing or advertisement is for reference only, the selling price will be determined at auction. There is NO starting bid, you may bid any amount.

4485 Gulf Of Mexico Drive Unit 402, Longboat Key

3070 Grand Bay Boulevard Unit 632, Longboat Key

$675,000

Experience ultimate maintenance-free coastal living in this move-in ready 2BR/2BA Bimini model, perfectly positioned behind the secure gates of Bay Isles in Grand Bay. Located on the third living level of Building 6, this exceptional residence features an expansive, nearly 400 sq. ft. wraparound terrace showcasing panoramic Sarasota Bay views and unforgettable sunrises and sunsets. No detail has been overlooked in this thoughtfully modernized home: • Kitchen & Systems: Significantly updated kitchen and new water heater (2026); high-efficiency variable-speed HVAC with humidity control, Wi-Fi thermostat, and 12-year compressor warranty (2024). • Appliances & Finishes: New refrigerator, washer, dryer, updated plumbing/lighting fixtures, and fresh paint (2023). • Luxury Conveniences: Hunter Douglas battery-operated, remote-controlled window treatments (2023) and a renewed, transferable Home-Tech service contract. Grand Bay offers a world-class resort lifestyle with two heated pools and spas, tennis courts, a fitness center, an active clubhouse, and scenic trails along the bay front, marina, and golf courses. Best of all, enjoy private beach access at the gated Bay Isles Beach Club on the Gulf of Mexico. Fine dining along Gulf of Mexico Drive, St. Armands Circle, and downtown Sarasota are all just minutes away.

2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code

Experience ultimate maintenance-free coastal living in this move-in ready 2BR/2BA Bimini model, perfectly positioned behind the secure gates of Bay Isles in Grand Bay. Located on the third living level of Building 6, this exceptional residence features an expansive, nearly 400 sq. ft. wraparound terrace showcasing panoramic Sarasota Bay views and unforgettable sunrises and sunsets. No detail has been overlooked in this thoughtfully modernized home: • Kitchen & Systems: Significantly updated kitchen and new water heater (2026); high-efficiency variable-speed HVAC with humidity control, Wi-Fi thermostat, and 12-year compressor warranty (2024). • Appliances & Finishes: New refrigerator, washer, dryer, updated plumbing/lighting fixtures, and fresh paint (2023). • Luxury Conveniences: Hunter Douglas battery-operated, remote-controlled window treatments (2023) and a renewed, transferable Home-Tech service contract. Grand Bay offers a world-class resort lifestyle with two heated pools and spas, tennis courts, a fitness center, an active clubhouse, and scenic trails along the bay front, marina, and golf courses. Best of all, enjoy private beach access at the gated Bay Isles Beach Club on the Gulf of Mexico. Fine dining along Gulf of Mexico Drive, St. Armands Circle, and downtown Sarasota are all just minutes away.

3070 Grand Bay Boulevard Unit 632, Longboat Key

$675,000

Virtually Staged. Views, views, views! A must see. Experience coastal elegance and stunning water views in this beautifully renovated two-bedroom, two-bath villa in the active Spanish Main Yacht Club waterfront community on Longboat Key. Porcelain tile flooring flows seamlessly throughout the home, highlighting a kitchen equipped with quartz countertops, stainless steel appliances, an undermount sink, custom tile herringbone backsplash and generous cabinet space. Crown molding elevates the open living room, which leads into a large lanai framed by hurricane-grade windows and blinds that showcase views of the Bay. The primary bedroom features a walk-in closet, while both baths display custom tile tastefully outfitted that completes this custom renovation. Outside, a large patio running along back of the home offers privacy provided by natural wetlands, with Bay access nearby to launch your kayak. Community amenities include private deeded beach access directly across the street, open water access with boat slips available for a nominal lease, a community heated swimming pool and a newly refreshed clubhouse. Enjoy beautifully landscaped grounds in a convenient location just minutes from St. Armands Circle and downtown Sarasota.

2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code

Virtually Staged. Views, views, views! A must see. Experience coastal elegance and stunning water views in this beautifully renovated two-bedroom, two-bath villa in the active Spanish Main Yacht Club waterfront community on Longboat Key. Porcelain tile flooring flows seamlessly throughout the home, highlighting a kitchen equipped with quartz countertops, stainless steel appliances, an undermount sink, custom tile herringbone backsplash and generous cabinet space. Crown molding elevates the open living room, which leads into a large lanai framed by hurricane-grade windows and blinds that showcase views of the Bay. The primary bedroom features a walk-in closet, while both baths display custom tile tastefully outfitted that completes this custom renovation. Outside, a large patio running along back of the home offers privacy provided by natural wetlands, with Bay access nearby to launch your kayak. Community amenities include private deeded beach access directly across the street, open water access with boat slips available for a nominal lease, a community heated swimming pool and a newly refreshed clubhouse. Enjoy beautifully landscaped grounds in a convenient location just minutes from St. Armands Circle and downtown Sarasota.

917 Spanish Drive N, Longboat Key

4835 Gulf Of Mexico Drive Unit 106, Longboat Key

$675,000

Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!

2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code

Waterfront Living on Longboat Key – Direct Gulf Access Experience the best of coastal living on beautiful Longboat Key. This first-floor residence offers effortless access and an unbeatable connection to the water, with direct access to the stunning Gulf of Mexico just steps from your door. Recently updated, the home features brand-new flooring throughout, along with all-new hurricane-impact windows, sliding glass doors, and a hurricane front door—providing peace of mind and modern comfort. Enjoy seamless indoor-outdoor living with easy walk-out access, perfect for morning beach strolls, sunset views, or simply embracing the relaxed Gulf Coast lifestyle. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property offers exceptional value in a highly sought-after location. Year after year, The Westchester has been considered to be the most sought after location on Gulf of Mexico Drive. This two bedroom, two bath 1,393 sq. ft. condominium holds many family memories, which could now be yours. Experience the beautiful views of the Emerald waters from both lanais. Unit has recently been completely painted. Unit is move-in ready to be enjoyed! Both bathrooms contain generous walk-in closets, with a washer/dryer installed in the guest closet. Come witness Resort Style amenities of two heated pools, beach cabanas, car wash station, a tennis and pickleball court, shuffleboard court, kayak rack, outdoor storage and a welcoming grilling convenience behind Club 72. This split plan, first floor, master en-suite unit awaits your TLC. Kitchen includes side-by-side beverage refrigerators. R&R IS THE PACE, LBK IS THE PLACE!!!!!

4835 Gulf Of Mexico Drive Unit 106, Longboat Key

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

$660,000

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

2 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code

Welcome to Paradise! Fall in love with this turnkey furnished two- bedroom two bath End Unit condo! Relax and enjoy beautiful unobstructed views of Sarasota Bay from nearly every room in the house. The bright newly remodeled open concept kitchen has new cabinetry, quartz countertops and a large breakfast bar. You can even catch a sunset from the oversized westerly kitchen window. On the far side of the home is the master suite with an ensuite bath with a walk-in shower and dual sink vanity. The walk-in closet has built-in shelves and is large enough to accommodate the one-year-old stackable washer and dryer. The second bedroom has built in closets and drawers along with a built-in desk making it ideal for guests or a home office. Both bedrooms access the lanai that has an amazing view with its floor to ceiling windows. Additional features in the home include a whole house water filter, hurricane impact windows 2023, HVAC 2021, water heater 2022,microwave and range 2023 and a brand-new refrigerator. This home is extremely spacious and provides ample storage. There are two linen closets, three walk in closets and three sets of custom boudoir built-ins. There is also a ground level private storage room at your assigned under building parking space which happens to be located next to the Elevator. This condo is also located directly across from one of the community pools. Enjoy three beach access points (including one private), 26 acres of tropical surroundings including a 1/2 mile of nature trails, two heated pools, fitness center and sauna, clubhouse, tennis and pickleball courts, boat docks (waitlist) kayak launches, kayak storage and two marinas. You are also just minutes away from championship golf courses, restaurants, shopping, St. Armands Circle, Downtown Sarasota, and Anna Marie Island. This waterfront condo community and its great location has something for everyone to enjoy!

4600 Gulf Of Mexico Drive Unit 301, Longboat Key

5260 Gulf Of Mexico Drive Unit 403, Longboat Key

$649,999

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

2 Beds ⋅ 2 Baths ⋅ Banyan Bay SubDv. ⋅ 34228 Zip Code

This beautifully maintained, ground-floor 2-bedroom, 2-bathroom condo in the desirable Banyan Bay Club offers an exceptional opportunity to own a spacious, modern / updated, move-in-ready home perfectly positioned in a charming, pet-friendly gulf-to-bay community. This unit combines convenience, amenities, and a relaxed coastal lifestyle—all at an outstanding location. This Banyan Bay condominium has an open floor plan with plank style ceramic tile throughout, recently updated featuring new cabinets, vanities, quartzite/quartz countertops and new stainless steel appliances; new Central Air system, and new hot water heater, in-unit full-size washer & dryer, modern tile design in bath, extra sleeping nook for added flexibility, tastefully furnished (can be sold furnished), private patio nestled under a majestic banyan tree-ideal for morning coffee or evening cocktails, large glass hurricane sliders & windows offering a garden view, fiber optic internet included for each unit. SQUARE FOOTAGE IN SLEEPING NOOK IS ADDED TO MAKE THE INTERIOR SQ FTG 1163. The resort-Style Community Amenities (steps from your door): heated community swimming pool, newly resurfaced tennis and pickleball court, fully equipped fitness center, clubhouse with social hall and full kitchen, new day dock, fishing pier, kayak/paddleboard launch, & storage, private gulf beach access with complimentary lounge chairs on the sand, assigned covered carport parking plus ample guest parking, exterior storage for beach gear, on-site manager and carefree exterior maintenance handled by the association, bicycle storage and mature tropical landscaping with giant banyan trees. Unbeatable Location-why Mid-Key is Best! Everything you need is within walking distance; numerous restaurants & cafes, boutiques, beautiful Durante Park with shaded trails and playground, 3 minute walk to your private Gulf beach, 1-minute walk to the community pool, gym, clubhouse, and courts,. This 44-unit condominium offers a social atmosphere, plenty of activities, up to 2 pets allowed (no weight or size limit). Whether you are seeking a full-time residence, vacation getaway, second home or investment property (valued returning renter’s incomes can offset HOA fees), this immaculate condo is ready for you to move in and start enjoying the island lifestyle today. Don't miss this combination of location, amenities and value on Longboat Key!

5260 Gulf Of Mexico Drive Unit 403, Longboat Key

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key

$649,900

THE BAY! THE GULF! THE BEST OF BOTH! Imagine a place where every day begins with the peaceful beauty of Longboat Key's sparkling bay and ends beneath the breathtaking colors of a Gulf Coast sunset. Perfectly positioned between both shores, this beautifully updated 3-bedroom, 2-bath end-unit villa offers the rare opportunity to experience the very best of island living from one exceptional location. Nestled within the highly sought-after waterfront community of Windward Bay, this 1,504-square-foot residence welcomes you with a sense of light, warmth, and effortless coastal elegance. As an end unit, the villa enjoys additional windows, enhanced privacy, and an abundance of natural sunlight throughout the day. Luxury vinyl plank flooring flows seamlessly through the living spaces, while custom plantation shutters add timeless character and refinement. The thoughtfully renovated kitchen blends style and functionality with granite countertops, beautiful soft-close cabinetry, and an inviting layout designed for everyday living and easy entertaining. The spacious great room opens effortlessly to a private outdoor patio, creating the perfect setting for morning coffee, afternoon relaxation, or dining beneath the coastal breeze. Life here is refreshingly simple. Ground-level living means no stairs, no elevators, and convenient parking just steps from your front door. Whether you're arriving home from the beach or carrying in groceries, everything about this villa is designed for easy, maintenance-free living. Equally impressive are the community improvements already in place. In 2020, the exterior was upgraded with hurricane-impact windows, hurricane-impact sliding glass doors, and a new roof, providing valuable peace of mind for years to come. Windward Bay has long been one of Longboat Key's most treasured communities, and it's easy to understand why. Set across 26 beautifully landscaped waterfront acres, residents enjoy three beach access points, a scenic half-mile nature trail, two heated swimming pools, fitness center, sauna, clubhouse, tennis and pickleball courts, kayak launches, covered parking, storage areas, and boat docks available by waitlist. Dolphins, manatees, tropical birds, and other native wildlife are frequent visitors, making every walk through the community feel like a nature retreat. Pet-friendly and financially strong, Windward Bay has completed both its Milestone Inspection and Capital Reserve Study. Monthly fees were reduced in 2025 and increased by only $13 for 2026, reflecting responsible community management and long-term stability. From this ideal location, you're just minutes from St. Armands Circle, Downtown Sarasota, Bridge Street, championship golf, waterfront dining, boutique shopping, and the exceptional arts and cultural attractions that make Florida's Gulf Coast so desirable. More than a beautiful villa, this is a lifestyle defined by sunshine, serenity, and connection to the water. A place where morning bay views, evening Gulf sunsets, and the ease of resort-style living become part of your everyday experience. THE BEST OF LONGBOAT KEY ISN'T ON THE BAY OR THE GULF... IT'S BETWEEN THEM. Welcome Home to Villa 8 at Windward Bay.

3 Beds ⋅ 2 Baths ⋅ Windward Bay SubDv. ⋅ 34228 Zip Code

THE BAY! THE GULF! THE BEST OF BOTH! Imagine a place where every day begins with the peaceful beauty of Longboat Key's sparkling bay and ends beneath the breathtaking colors of a Gulf Coast sunset. Perfectly positioned between both shores, this beautifully updated 3-bedroom, 2-bath end-unit villa offers the rare opportunity to experience the very best of island living from one exceptional location. Nestled within the highly sought-after waterfront community of Windward Bay, this 1,504-square-foot residence welcomes you with a sense of light, warmth, and effortless coastal elegance. As an end unit, the villa enjoys additional windows, enhanced privacy, and an abundance of natural sunlight throughout the day. Luxury vinyl plank flooring flows seamlessly through the living spaces, while custom plantation shutters add timeless character and refinement. The thoughtfully renovated kitchen blends style and functionality with granite countertops, beautiful soft-close cabinetry, and an inviting layout designed for everyday living and easy entertaining. The spacious great room opens effortlessly to a private outdoor patio, creating the perfect setting for morning coffee, afternoon relaxation, or dining beneath the coastal breeze. Life here is refreshingly simple. Ground-level living means no stairs, no elevators, and convenient parking just steps from your front door. Whether you're arriving home from the beach or carrying in groceries, everything about this villa is designed for easy, maintenance-free living. Equally impressive are the community improvements already in place. In 2020, the exterior was upgraded with hurricane-impact windows, hurricane-impact sliding glass doors, and a new roof, providing valuable peace of mind for years to come. Windward Bay has long been one of Longboat Key's most treasured communities, and it's easy to understand why. Set across 26 beautifully landscaped waterfront acres, residents enjoy three beach access points, a scenic half-mile nature trail, two heated swimming pools, fitness center, sauna, clubhouse, tennis and pickleball courts, kayak launches, covered parking, storage areas, and boat docks available by waitlist. Dolphins, manatees, tropical birds, and other native wildlife are frequent visitors, making every walk through the community feel like a nature retreat. Pet-friendly and financially strong, Windward Bay has completed both its Milestone Inspection and Capital Reserve Study. Monthly fees were reduced in 2025 and increased by only $13 for 2026, reflecting responsible community management and long-term stability. From this ideal location, you're just minutes from St. Armands Circle, Downtown Sarasota, Bridge Street, championship golf, waterfront dining, boutique shopping, and the exceptional arts and cultural attractions that make Florida's Gulf Coast so desirable. More than a beautiful villa, this is a lifestyle defined by sunshine, serenity, and connection to the water. A place where morning bay views, evening Gulf sunsets, and the ease of resort-style living become part of your everyday experience. THE BEST OF LONGBOAT KEY ISN'T ON THE BAY OR THE GULF... IT'S BETWEEN THEM. Welcome Home to Villa 8 at Windward Bay.

4750 Gulf Of Mexico Drive Unit Villa 8, Longboat Key

4234 Gulf Of Mexico Drive Unit M1, Longboat Key

$649,000

COMMUNITY BOAT SLIP AVAILABLE! It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. At this writing, community has two 30 ft boat slips available at $600 per year. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!

2 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv. ⋅ 34228 Zip Code

COMMUNITY BOAT SLIP AVAILABLE! It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. At this writing, community has two 30 ft boat slips available at $600 per year. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!

4234 Gulf Of Mexico Drive Unit M1, Longboat Key

6701 Gulf Of Mexico Drive Unit 332, Longboat Key

$649,000

Here is a rare opportunity to own a walk-out, gulf-front beach condo on Longboat Key. Tucked just behind a beach-grass dune and set on a grassy knoll, this one-bedroom residence is ideally positioned to capture refreshing sea breezes and spectacular sunset views. The natural topography also helps protect the building from heavy weather and water intrusion. Remodeled Interior and Modern Upgrades: Completely remodeled, this unique one-bedroom condo now features a desirable two-bathroom floor plan. The newly designed open kitchen includes premium appliances, upgraded stone countertops, and new cabinetry, creating a bright and functional space for everyday living and entertaining. Updates continue throughout the residence, including hurricane-impact sliding doors, a new front window, and beautifully modernized bathrooms. The condo is being sold turn-key, with everything included for a seamless move-in experience. Inside, the open, light-filled layout maximizes both space and natural beauty. Large glass sliders connect the living area to the outdoors, filling the kitchen and main living space with sunlight while blending coastal charm with modern functionality. The bedroom and bathrooms are thoughtfully designed to provide comfortable, serene retreats. Private Outdoor Living: The distinctive ground-floor Whitney Beach Gulfside floor plan offers two inviting outdoor spaces: a front privacy-fenced enclosed patio, ideal for alfresco dining or beachfront gardening, and a rear open patio perfect for relaxing. Whether you are enjoying morning coffee or an evening cocktail, the gentle sea breeze creates a peaceful setting for unwinding. Resort-Style Community Amenities: Whitney Beach offers a range of well-maintained amenities designed to enhance the coastal lifestyle, including: Sparkling community pool , Tennis courts and shuffleboard, Beach chairs for relaxed days by the Gulf, Boat slips available, Tranquil bayou pavilion for water enthusiasts. Unmatched Longboat Key Location: Located on the quiet northern end of Longboat Key, Whitney Beach places you close to excellent restaurants, shops, and everyday conveniences. Enjoy easy access by foot, bike, or car, with St. Armands Circle just a short drive away. Flexible Living and Investment Potential. This condo combines a highly desirable gulf-front location with the privacy, comfort, and ease of a casual beachfront lifestyle. It is well suited for year-round living, a seasonal retreat, or a smart investment opportunity. With one-month minimum rentals allowed up to 12 times per year, the property offers strong rental flexibility. As an added bonus, the community features two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, helping provide a no-surprises ownership experience. Discover Longboat Key: Enjoy the best of Longboat Key, where luxury meets laid-back coastal charm. Schedule your private tour today.

1 Beds ⋅ 2 Baths ⋅ Whitney Beach SubDv. ⋅ 34228 Zip Code

Here is a rare opportunity to own a walk-out, gulf-front beach condo on Longboat Key. Tucked just behind a beach-grass dune and set on a grassy knoll, this one-bedroom residence is ideally positioned to capture refreshing sea breezes and spectacular sunset views. The natural topography also helps protect the building from heavy weather and water intrusion. Remodeled Interior and Modern Upgrades: Completely remodeled, this unique one-bedroom condo now features a desirable two-bathroom floor plan. The newly designed open kitchen includes premium appliances, upgraded stone countertops, and new cabinetry, creating a bright and functional space for everyday living and entertaining. Updates continue throughout the residence, including hurricane-impact sliding doors, a new front window, and beautifully modernized bathrooms. The condo is being sold turn-key, with everything included for a seamless move-in experience. Inside, the open, light-filled layout maximizes both space and natural beauty. Large glass sliders connect the living area to the outdoors, filling the kitchen and main living space with sunlight while blending coastal charm with modern functionality. The bedroom and bathrooms are thoughtfully designed to provide comfortable, serene retreats. Private Outdoor Living: The distinctive ground-floor Whitney Beach Gulfside floor plan offers two inviting outdoor spaces: a front privacy-fenced enclosed patio, ideal for alfresco dining or beachfront gardening, and a rear open patio perfect for relaxing. Whether you are enjoying morning coffee or an evening cocktail, the gentle sea breeze creates a peaceful setting for unwinding. Resort-Style Community Amenities: Whitney Beach offers a range of well-maintained amenities designed to enhance the coastal lifestyle, including: Sparkling community pool , Tennis courts and shuffleboard, Beach chairs for relaxed days by the Gulf, Boat slips available, Tranquil bayou pavilion for water enthusiasts. Unmatched Longboat Key Location: Located on the quiet northern end of Longboat Key, Whitney Beach places you close to excellent restaurants, shops, and everyday conveniences. Enjoy easy access by foot, bike, or car, with St. Armands Circle just a short drive away. Flexible Living and Investment Potential. This condo combines a highly desirable gulf-front location with the privacy, comfort, and ease of a casual beachfront lifestyle. It is well suited for year-round living, a seasonal retreat, or a smart investment opportunity. With one-month minimum rentals allowed up to 12 times per year, the property offers strong rental flexibility. As an added bonus, the community features two-story buildings and is exempt from Florida’s Milestone inspection and reporting requirements, helping provide a no-surprises ownership experience. Discover Longboat Key: Enjoy the best of Longboat Key, where luxury meets laid-back coastal charm. Schedule your private tour today.

6701 Gulf Of Mexico Drive Unit 332, Longboat Key

$645,000

GULF-TO-BAY LIVING ON LONGBOAT KEY—WHERE EVERY DAY FEELS LIKE A GETAWAY! Welcome to Bayport Beach & Tennis Club, a truly special Gulf-to-Bay community surrounded by lush tropical landscaping, pristine beach access, beautiful sunsets, and resort-style amenities. This desirable 2-bedroom, 2-bath SECOND-FLOOR END UNIT offers a wonderful sense of privacy, abundant natural light, and the added advantage of NO NEIGHBORS ABOVE YOU. Inside, the bright and welcoming layout features an open living and dining area that is perfect for both everyday comfort and entertaining. The thoughtfully designed split-bedroom floor plan provides separation and privacy for owners and guests. The kitchen and bathrooms have been tastefully updated, newer windows add comfort and efficiency, and a full-size washer and dryer inside the residence make daily living easy. The spacious primary suite includes a walk-in closet along with a versatile bonus area that works beautifully as a home office, reading nook, or additional storage space. Step outside and enjoy the best of Florida living. Sip your morning coffee on the open-air deck surrounded by tropical scenery, or relax on the screened lanai and take in the peaceful surroundings. Covered parking, convenient guest parking, multiple storage areas, and a private owner’s closet add the practical conveniences that make this island retreat even more appealing. THE BAYPORT LIFESTYLE IS WHAT TRULY SETS THIS COMMUNITY APART! Spanning approximately 27 beautifully landscaped acres from the Gulf of Mexico to Sarasota Bay, Bayport offers approximately 1,200 FEET OF PRIVATE GULF BEACH ACCESS, where soft sand, turquoise water, and unforgettable sunsets are just moments from home. Residents enjoy an impressive array of amenities, including a heated Junior Olympic-size swimming pool, four Har-Tru tennis courts, a fitness center, kayak launch, fishing pier, and beach chairs and umbrellas. Meandering pathways wind through mature tropical landscaping, creating a serene, park-like setting that gives Bayport its distinctive charm. And the location is hard to beat! Enjoy easy access to Longboat Key’s restaurants and boutique shopping, along with nearby St. Armands Circle and the cultural attractions of downtown Sarasota. Imagine beginning your day with a quiet walk along the Gulf, spending the afternoon kayaking on Sarasota Bay, and finishing the evening with another breathtaking Florida sunset. Whether you’re looking for a full-time residence, seasonal retreat, or coastal escape, this is a wonderful opportunity to experience everything that makes Longboat Key so special. BEACH. BAY. ISLAND LIVING. YOUR LITTLE PIECE OF PARADISE AWAITS AT BAYPORT BEACH & TENNIS CLUB!

2 Beds ⋅ 2 Baths ⋅ Bayport Bch & Ten SubDv. ⋅ 34228 Zip Code

GULF-TO-BAY LIVING ON LONGBOAT KEY—WHERE EVERY DAY FEELS LIKE A GETAWAY! Welcome to Bayport Beach & Tennis Club, a truly special Gulf-to-Bay community surrounded by lush tropical landscaping, pristine beach access, beautiful sunsets, and resort-style amenities. This desirable 2-bedroom, 2-bath SECOND-FLOOR END UNIT offers a wonderful sense of privacy, abundant natural light, and the added advantage of NO NEIGHBORS ABOVE YOU. Inside, the bright and welcoming layout features an open living and dining area that is perfect for both everyday comfort and entertaining. The thoughtfully designed split-bedroom floor plan provides separation and privacy for owners and guests. The kitchen and bathrooms have been tastefully updated, newer windows add comfort and efficiency, and a full-size washer and dryer inside the residence make daily living easy. The spacious primary suite includes a walk-in closet along with a versatile bonus area that works beautifully as a home office, reading nook, or additional storage space. Step outside and enjoy the best of Florida living. Sip your morning coffee on the open-air deck surrounded by tropical scenery, or relax on the screened lanai and take in the peaceful surroundings. Covered parking, convenient guest parking, multiple storage areas, and a private owner’s closet add the practical conveniences that make this island retreat even more appealing. THE BAYPORT LIFESTYLE IS WHAT TRULY SETS THIS COMMUNITY APART! Spanning approximately 27 beautifully landscaped acres from the Gulf of Mexico to Sarasota Bay, Bayport offers approximately 1,200 FEET OF PRIVATE GULF BEACH ACCESS, where soft sand, turquoise water, and unforgettable sunsets are just moments from home. Residents enjoy an impressive array of amenities, including a heated Junior Olympic-size swimming pool, four Har-Tru tennis courts, a fitness center, kayak launch, fishing pier, and beach chairs and umbrellas. Meandering pathways wind through mature tropical landscaping, creating a serene, park-like setting that gives Bayport its distinctive charm. And the location is hard to beat! Enjoy easy access to Longboat Key’s restaurants and boutique shopping, along with nearby St. Armands Circle and the cultural attractions of downtown Sarasota. Imagine beginning your day with a quiet walk along the Gulf, spending the afternoon kayaking on Sarasota Bay, and finishing the evening with another breathtaking Florida sunset. Whether you’re looking for a full-time residence, seasonal retreat, or coastal escape, this is a wonderful opportunity to experience everything that makes Longboat Key so special. BEACH. BAY. ISLAND LIVING. YOUR LITTLE PIECE OF PARADISE AWAITS AT BAYPORT BEACH & TENNIS CLUB!

843 Bayport Way Unit 843, Longboat Key

2110 Harbourside Drive Unit 523, Longboat Key

$628,000

Best value with SRQ Bay Views- great location. 3 bedrooms. Discover a relaxed island lifestyle at The Atrium in Bay Isles, where expansive water views and a generous, comfortable floor plan meet in this three-bedroom, two-bath residence. With 2,031 square feet of living space, this home offers room to gather and enjoy Longboat Key's natural beauty. A broad wraparound, covered balcony extends the living space outdoors and frames sweeping views across Sarasota Bay and the surrounding waterways. Start the day with coffee as the light moves across the water, or settle in at day’s end to watch the colors shift over the bay. The balcony’s generous proportions create multiple places to dine, read, or simply take in the coastal setting. Inside, the open living and dining area is designed for easy everyday living and entertaining. High ceilings, an open floor plan, and a wall of windows bring in natural light and keep the water view in focus. The spacious kitchen offers abundant cabinetry, stainless steel appliances, and a double oven, with plenty of room to prepare a casual breakfast or host a dinner with friends. A separate laundry room adds convenience. The primary suite provides a peaceful retreat, with a walk-in closet and a private bath. Two additional bedrooms offer flexibility for guests, a home office, or hobbies, while the second full bath serves both visitors and residents. Offered with furnishings negotiable, the residence gives its next owner the opportunity to make the space their own. The Atrium’s amenities support an active, easygoing island routine. Residents enjoy a gated setting with elevator access, a fitness center, a community pool, and tennis courts. Deeded beach access makes it easy to spend time on the Gulf of Mexico, while the community’s bayfront setting offers a different perspective on the island’s waters. A one-car garage and guest parking provide practical convenience. Located within Bay Isles on Longboat Key, the property is close to the island’s beaches, golf, boating, dining, and shopping. St. Armands Circle and downtown Sarasota are close, with restaurants, boutiques, cultural attractions, and waterfront events within reach. Whether you are looking for a full-time island home, a seasonal escape, or a place to enjoy between travels, this residence offers generous space, memorable bay views, and access to the best of the Longboat Key lifestyle.

3 Beds ⋅ 2 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Best value with SRQ Bay Views- great location. 3 bedrooms. Discover a relaxed island lifestyle at The Atrium in Bay Isles, where expansive water views and a generous, comfortable floor plan meet in this three-bedroom, two-bath residence. With 2,031 square feet of living space, this home offers room to gather and enjoy Longboat Key's natural beauty. A broad wraparound, covered balcony extends the living space outdoors and frames sweeping views across Sarasota Bay and the surrounding waterways. Start the day with coffee as the light moves across the water, or settle in at day’s end to watch the colors shift over the bay. The balcony’s generous proportions create multiple places to dine, read, or simply take in the coastal setting. Inside, the open living and dining area is designed for easy everyday living and entertaining. High ceilings, an open floor plan, and a wall of windows bring in natural light and keep the water view in focus. The spacious kitchen offers abundant cabinetry, stainless steel appliances, and a double oven, with plenty of room to prepare a casual breakfast or host a dinner with friends. A separate laundry room adds convenience. The primary suite provides a peaceful retreat, with a walk-in closet and a private bath. Two additional bedrooms offer flexibility for guests, a home office, or hobbies, while the second full bath serves both visitors and residents. Offered with furnishings negotiable, the residence gives its next owner the opportunity to make the space their own. The Atrium’s amenities support an active, easygoing island routine. Residents enjoy a gated setting with elevator access, a fitness center, a community pool, and tennis courts. Deeded beach access makes it easy to spend time on the Gulf of Mexico, while the community’s bayfront setting offers a different perspective on the island’s waters. A one-car garage and guest parking provide practical convenience. Located within Bay Isles on Longboat Key, the property is close to the island’s beaches, golf, boating, dining, and shopping. St. Armands Circle and downtown Sarasota are close, with restaurants, boutiques, cultural attractions, and waterfront events within reach. Whether you are looking for a full-time island home, a seasonal escape, or a place to enjoy between travels, this residence offers generous space, memorable bay views, and access to the best of the Longboat Key lifestyle.

2110 Harbourside Drive Unit 523, Longboat Key

2301 Gulf Of Mexico Drive Unit 44N, Longboat Key

$625,000

Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.

2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv. ⋅ 34228 Zip Code

Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.

2301 Gulf Of Mexico Drive Unit 44N, Longboat Key

1920 Harbourside Drive Unit 1003, Longboat Key

$624,900

Virtually Staged. Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. Access to Bay Isles EXCLUSIVE Beach Club right across the street! The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities. Optional membership in the Longboat Key Club offers access, depending on membership category, to 45 holes of championship golf, more than 20 Har-Tru tennis courts, pickleball, multiple dining venues, private beach and pool facilities, a full-service spa, fitness and wellness facilities, member events, Marina Village and the Club’s deep-water marina.

2 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code

Virtually Staged. Start your day with glowing sunrise views across Sarasota Bay from the living room, primary suite, and screened lanai, where the waterfront setting makes every moment feel like a retreat. Located within the gated waterfront enclave of Bay Isles, this spacious 2-bedroom, 2.5-bath townhome offers effortless island living with serene bay views and a flexible layout. Access to Bay Isles EXCLUSIVE Beach Club right across the street! The main living level is thoughtfully designed for everyday living and entertaining, featuring an open living and dining area complemented by a wood-burning fireplace. The kitchen offers ample space for casual meals and future customization. Large sliders extend the living space to a screened lanai overlooking the bay—an ideal spot to unwind or host guests. Hurricane shutters are already installed, offering added security and peace of mind. Upstairs, two well-proportioned bedroom suites each include private baths and walk-in closets, providing comfort and privacy for owners and guests alike. The primary suite is highlighted by a light-filled bath with an oversized soaking tub with jets and skylights above, creating a relaxing, spa-inspired atmosphere. A versatile loft area with additional skylights offers flexibility for a home office or gym, den, or reading space. On the ground level, an oversized two-car tandem garage delivers exceptional storage and functionality, with room for hobbies or a workshop. Residents of Fairway Bay enjoy a pet-friendly environment, professional on-site management, lushly landscaped walking and biking paths, and a private heated pool. Ownership also includes access to the exclusive Bay Isles Beach Club, a private Gulf-front amenity offering pavilion seating, tropical cabanas, grilling and picnic areas, beach storage, kitchen prep, and private restroom facilities. Ideally situated near the beaches, golf, dining, and shopping of Longboat Key, this townhome presents a rare opportunity to own in one of the island’s most established and desirable communities. Optional membership in the Longboat Key Club offers access, depending on membership category, to 45 holes of championship golf, more than 20 Har-Tru tennis courts, pickleball, multiple dining venues, private beach and pool facilities, a full-service spa, fitness and wellness facilities, member events, Marina Village and the Club’s deep-water marina.

1920 Harbourside Drive Unit 1003, Longboat Key

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