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THE SWEET SPOT OF ANNA MARIA ISLAND Some locations simply capture everything there is to love about Anna Maria Island, and 706 North Shore Drive is one of them! Tucked into the coveted north end of the island, just around the corner from the beautiful Gulf beaches at Cypress Avenue and an easy stroll to the shops, restaurants and charm of Pine Avenue, this beautifully renovated coastal retreat puts the very best of island living right at your doorstep. Already a popular and consistently booked vacation rental, this furnished three-bedroom, two-bath home combines an exceptional location, inviting coastal style and the relaxed indoor-outdoor lifestyle that makes Anna Maria Island so special. Inside, wood-plank ceilings, crown molding, wood-look tile flooring and abundant natural light create a warm, welcoming atmosphere. The beautifully appointed kitchen features distinctive nautical lighting and a contrasting center island that naturally becomes a gathering place for family and friends. An adjoining dining area and comfortable living spaces make entertaining effortless. The primary suite features an ensuite bath with double vanities and a walk-in shower, while a spacious bonus room direct pool access offers wonderful flexibility for guests or additional living space. Outside, a private tropical paradise awaits. Lush landscaping and privacy fencing surround the heated pool and spa, with generous paver patios for outdoor dining, entertaining and relaxing in the Florida sunshine. An outdoor hot-and-cold shower is perfect after a day at the beach. The rear-entry garage, complete with built-in storage and laundry facilities, is an especially welcome feature for second-home owners looking for space to keep their island essentials. But it's the location that truly sets this home apart. With the Cypress Avenue beach access just around the corner and Pine Avenue nearby, mornings can begin with a walk along the Gulf, afternoons can unfold by your private pool, and evenings can end with one of Anna Maria Island's unforgettable sunsets. Whether you're searching for a personal island getaway, a full-time coastal residence or an established vacation rental with a strong history of bookings, 706 North Shore Drive offers a wonderful opportunity to enjoy Anna Maria Island at its best. The beach, the neighborhood, the island lifestyle. It's all right here.

3 Beds ⋅ 2 Baths ⋅ Wells Terrace SubDv. ⋅ 34216 Zip Code

THE SWEET SPOT OF ANNA MARIA ISLAND Some locations simply capture everything there is to love about Anna Maria Island, and 706 North Shore Drive is one of them! Tucked into the coveted north end of the island, just around the corner from the beautiful Gulf beaches at Cypress Avenue and an easy stroll to the shops, restaurants and charm of Pine Avenue, this beautifully renovated coastal retreat puts the very best of island living right at your doorstep. Already a popular and consistently booked vacation rental, this furnished three-bedroom, two-bath home combines an exceptional location, inviting coastal style and the relaxed indoor-outdoor lifestyle that makes Anna Maria Island so special. Inside, wood-plank ceilings, crown molding, wood-look tile flooring and abundant natural light create a warm, welcoming atmosphere. The beautifully appointed kitchen features distinctive nautical lighting and a contrasting center island that naturally becomes a gathering place for family and friends. An adjoining dining area and comfortable living spaces make entertaining effortless. The primary suite features an ensuite bath with double vanities and a walk-in shower, while a spacious bonus room direct pool access offers wonderful flexibility for guests or additional living space. Outside, a private tropical paradise awaits. Lush landscaping and privacy fencing surround the heated pool and spa, with generous paver patios for outdoor dining, entertaining and relaxing in the Florida sunshine. An outdoor hot-and-cold shower is perfect after a day at the beach. The rear-entry garage, complete with built-in storage and laundry facilities, is an especially welcome feature for second-home owners looking for space to keep their island essentials. But it's the location that truly sets this home apart. With the Cypress Avenue beach access just around the corner and Pine Avenue nearby, mornings can begin with a walk along the Gulf, afternoons can unfold by your private pool, and evenings can end with one of Anna Maria Island's unforgettable sunsets. Whether you're searching for a personal island getaway, a full-time coastal residence or an established vacation rental with a strong history of bookings, 706 North Shore Drive offers a wonderful opportunity to enjoy Anna Maria Island at its best. The beach, the neighborhood, the island lifestyle. It's all right here.

706 N Shore Drive, Anna Maria

$2,495,000

Build big. Live the dream. Welcome to Anna Maria! Oversized canal-front lots like this are rare: just a pinch shy of one-third of an acre, with a sweeping 93 feet of water frontage and direct boating access to Tampa Bay and the Gulf. Add a shared boat basin, and this is a boater’s paradise! The existing home is a teardown, and the property is being sold for land value. Bring your vision and create a show-stopping custom coastal estate or a high-performing investment in a coveted short-term rental zone. The possibilities are endless! Walk to sugar-sand Gulf beaches, then enjoy island boutiques, waterfront dining and the laid-back charm that makes Anna Maria Island legendary. Opportunities like this don’t last. Seize it!

3 Beds ⋅ 2 Baths ⋅ Bimini Bay Estates SubDv. ⋅ 34216 Zip Code

Build big. Live the dream. Welcome to Anna Maria! Oversized canal-front lots like this are rare: just a pinch shy of one-third of an acre, with a sweeping 93 feet of water frontage and direct boating access to Tampa Bay and the Gulf. Add a shared boat basin, and this is a boater’s paradise! The existing home is a teardown, and the property is being sold for land value. Bring your vision and create a show-stopping custom coastal estate or a high-performing investment in a coveted short-term rental zone. The possibilities are endless! Walk to sugar-sand Gulf beaches, then enjoy island boutiques, waterfront dining and the laid-back charm that makes Anna Maria Island legendary. Opportunities like this don’t last. Seize it!

225 Chilson Avenue, Anna Maria

$2,495,000

Welcome to this fully renovated 3-bedroom, 2.5-bathroom coastal retreat on the coveted north end of Anna Maria Island. Nestled in the desirable Shore Acres neighborhood, this single-story home (approximately 1,759 sq ft living area on a generous ~0.235-acre lot) has been thoughtfully updated with clean modern finishes, abundant natural light, and effortless indoor-outdoor flow that captures the essence of island living. The bright, open interior features light wood ceilings, crisp white walls, and expansive windows and sliding glass doors that invite the Florida sunshine indoors. A stylish dining area opens directly to a private outdoor space perfect for morning coffee or evening gatherings. There is room for a pool to add if desired. The fully renovated kitchen and living areas are designed for both everyday comfort and entertaining, while the three bedrooms and 2.5 baths provide flexible space for family, guests, or a primary suite retreat. Outside, a covered carport and entry with warm wood ceilings and clean architectural lines create a welcoming arrival. Tropical landscaping with mature palms and native plantings frames the property, offering privacy and a true coastal vibe. Just steps from the sugar-white sands and sunsets of Bean Point, beach access is right next to the property. Close to Pine Ave shops, restaurants, and more! Whether you’re seeking a full-time residence, weekend escape, or investment opportunity on one of Florida’s most sought-after barrier islands, 815 N Shore Drive is move-in ready and beautifully positioned for island living.

3 Beds ⋅ 3 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code

Welcome to this fully renovated 3-bedroom, 2.5-bathroom coastal retreat on the coveted north end of Anna Maria Island. Nestled in the desirable Shore Acres neighborhood, this single-story home (approximately 1,759 sq ft living area on a generous ~0.235-acre lot) has been thoughtfully updated with clean modern finishes, abundant natural light, and effortless indoor-outdoor flow that captures the essence of island living. The bright, open interior features light wood ceilings, crisp white walls, and expansive windows and sliding glass doors that invite the Florida sunshine indoors. A stylish dining area opens directly to a private outdoor space perfect for morning coffee or evening gatherings. There is room for a pool to add if desired. The fully renovated kitchen and living areas are designed for both everyday comfort and entertaining, while the three bedrooms and 2.5 baths provide flexible space for family, guests, or a primary suite retreat. Outside, a covered carport and entry with warm wood ceilings and clean architectural lines create a welcoming arrival. Tropical landscaping with mature palms and native plantings frames the property, offering privacy and a true coastal vibe. Just steps from the sugar-white sands and sunsets of Bean Point, beach access is right next to the property. Close to Pine Ave shops, restaurants, and more! Whether you’re seeking a full-time residence, weekend escape, or investment opportunity on one of Florida’s most sought-after barrier islands, 815 N Shore Drive is move-in ready and beautifully positioned for island living.

815 N Shore Drive, Anna Maria

$2,690,000

Under Construction. Why buy before December 31, 2026? Review recently passed Florida Amendment 3 with your CPA/tax advisor for potential tax advantages! Welcome to this completely updated charming coastal home located at 259 Gladiolus St in the desirable City of Anna Maria. If you’re looking for a ground level waterfront, 4-bedrooms, 3-bathrooms, pool home on the north-end, that is close to the beach, Pine Ave shops and the bayside park, this is one to come see! The interior and exterior design offers endless charming coastal details that lean into island relaxed style. As you walk through the double glass front doors, you’ll be surprised by how much light shines into this home accentuating the high ceilings and open concept. The design selections are classic and calm, from neutrals to soft beachy blues. The home offers a split floor plan and two master ensuites plus an inside utility that takes the chore out of laundry. As you make your way to the back of the home the water views become the focal point. The home layout makes every day enjoyment of island living, including the pool and spa that has multiple water features to create relaxing sounds and set the stage for backyard fun. The waterfront setting is tranquil and a fabulous setting for dockside fishing, kayaks or even boating with two bridges to bay. The list of new items includes interior walls and open concept layout, electric, plumbing, flooring, kitchen, appliances, bathrooms, inside utility, metal roof, Therma Tru impact glass front door and PGT impact windows and sliding doors, heated pool/spa, tropical landscaping, and including low maintenance artificial turf. Whether you’re looking for your own island destination to call home or the ideal rental income property with flexible rental restrictions this is one to consider. Call today to schedule your private showing.

4 Beds ⋅ 3 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code

Under Construction. Why buy before December 31, 2026? Review recently passed Florida Amendment 3 with your CPA/tax advisor for potential tax advantages! Welcome to this completely updated charming coastal home located at 259 Gladiolus St in the desirable City of Anna Maria. If you’re looking for a ground level waterfront, 4-bedrooms, 3-bathrooms, pool home on the north-end, that is close to the beach, Pine Ave shops and the bayside park, this is one to come see! The interior and exterior design offers endless charming coastal details that lean into island relaxed style. As you walk through the double glass front doors, you’ll be surprised by how much light shines into this home accentuating the high ceilings and open concept. The design selections are classic and calm, from neutrals to soft beachy blues. The home offers a split floor plan and two master ensuites plus an inside utility that takes the chore out of laundry. As you make your way to the back of the home the water views become the focal point. The home layout makes every day enjoyment of island living, including the pool and spa that has multiple water features to create relaxing sounds and set the stage for backyard fun. The waterfront setting is tranquil and a fabulous setting for dockside fishing, kayaks or even boating with two bridges to bay. The list of new items includes interior walls and open concept layout, electric, plumbing, flooring, kitchen, appliances, bathrooms, inside utility, metal roof, Therma Tru impact glass front door and PGT impact windows and sliding doors, heated pool/spa, tropical landscaping, and including low maintenance artificial turf. Whether you’re looking for your own island destination to call home or the ideal rental income property with flexible rental restrictions this is one to consider. Call today to schedule your private showing.

259 Gladiolus Street, Anna Maria

$1,175,000

Set in the heart of Anna Maria, this elevated 3BD/2BA home holds one of the island's most enviable addresses — around the corner to the Anna Maria City Pier and steps from the bay. Celebrated dining, open water, and the island's unhurried rhythm are all right outside the door. Inside, an open living and kitchen area, generous deck space, and a two-car garage offer a solid canvas. Update it, reimagine it, or start fresh — the potential here is wide open. Better still, the home sits in a short-term rental zone, so it can earn its keep between your own stays. Then step outside, where the Anna Maria lifestyle takes over: mornings on the beach, afternoons cruising the island by bike or golf cart, evenings fishing the pier or watching the sun drop into the Gulf. Locally loved shops and restaurants sit just down the street. Location, rental potential, and a lifestyle people rearrange their lives for. Bring your vision.

3 Beds ⋅ 2 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

Set in the heart of Anna Maria, this elevated 3BD/2BA home holds one of the island's most enviable addresses — around the corner to the Anna Maria City Pier and steps from the bay. Celebrated dining, open water, and the island's unhurried rhythm are all right outside the door. Inside, an open living and kitchen area, generous deck space, and a two-car garage offer a solid canvas. Update it, reimagine it, or start fresh — the potential here is wide open. Better still, the home sits in a short-term rental zone, so it can earn its keep between your own stays. Then step outside, where the Anna Maria lifestyle takes over: mornings on the beach, afternoons cruising the island by bike or golf cart, evenings fishing the pier or watching the sun drop into the Gulf. Locally loved shops and restaurants sit just down the street. Location, rental potential, and a lifestyle people rearrange their lives for. Bring your vision.

524 Spring Avenue, Anna Maria

$1,795,000

This amazing old Florida 1922 cottage is so quaint and cozy, you’ll never want to leave! This 3 bedroom, 3 bath island oasis is on a huge lot. With a heated pool and spa, surrounded in landscaping with a pool cabana including a TV, dining table and grill for family gatherings. Once you step through the door you will never want to leave this historic home with high end finishes and beautiful turnkey furnishings. The master suite is spacious with impact sliders on the whole wall looking out to the pool and cabana making it so private. Tile wood throughout, stainless steel appliances, beautiful countertops, there is so much this home has to offer. Living and kitchen open concept with an eat-in dining table in the kitchen. The 2nd bedroom has its own ensuite bath with a walk-in shower. 3rd bedroom is off the kitchen and uses the hallway full bath. Enjoy coffee on the back porch in the mornings listing to the birds chirp. Short walk to the shops and dining on Pine Avenue or stroll to the bay or beach as both are a short walk away. 1-7 day rentals are permitted, and bookings are in place making it easy to turn the key and it's vacation rental ready. This little island oasis is ready for you to enjoy paradise today!

3 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

This amazing old Florida 1922 cottage is so quaint and cozy, you’ll never want to leave! This 3 bedroom, 3 bath island oasis is on a huge lot. With a heated pool and spa, surrounded in landscaping with a pool cabana including a TV, dining table and grill for family gatherings. Once you step through the door you will never want to leave this historic home with high end finishes and beautiful turnkey furnishings. The master suite is spacious with impact sliders on the whole wall looking out to the pool and cabana making it so private. Tile wood throughout, stainless steel appliances, beautiful countertops, there is so much this home has to offer. Living and kitchen open concept with an eat-in dining table in the kitchen. The 2nd bedroom has its own ensuite bath with a walk-in shower. 3rd bedroom is off the kitchen and uses the hallway full bath. Enjoy coffee on the back porch in the mornings listing to the birds chirp. Short walk to the shops and dining on Pine Avenue or stroll to the bay or beach as both are a short walk away. 1-7 day rentals are permitted, and bookings are in place making it easy to turn the key and it's vacation rental ready. This little island oasis is ready for you to enjoy paradise today!

504 Spring Avenue, Anna Maria

$2,495,000

Discover the ultimate island retreat just three homes from the sugar-white sands and turquoise waters of the Gulf of Mexico. Situated on an oversized 8,250-square-foot lot, this beautifully appointed 4-bedroom, 3-bath home offers nearly 1,700 square feet of coastal living and features a desirable open floor plan designed for gathering and entertaining. The thoughtfully designed layout includes two spacious ensuite bedrooms, a fun bunk room perfect for younger guests, and plenty of room to relax after a day at the beach. Step outside to your own private tropical oasis. The heated pool invites you to enjoy sunny afternoons and evening swims under the stars, while the expansive backyard offers abundant space for lounging, grilling, and making memories with family and friends. The generous lot size is a rarity on Anna Maria Island and provides a true sense of privacy and room to spread out. Along the side of the home, an outdoor game area creates the perfect setting for friendly competitions and endless entertainment after a day spent on the beach. Ideally located in the heart of Anna Maria Island, you're just a short stroll to the boutiques, restaurants, and vibrant atmosphere of Pine Avenue, as well as the island's world-famous beaches. Whether enjoying spectacular Gulf sunsets, dining at one of the island's favorite eateries, or relaxing poolside with loved ones, this home embodies the laid-back luxury of island living. With a proven history as a successful short-term rental and exceptional investment opportunity, this turnkey property offers the perfect blend of lifestyle and income potential. Rarely do homes on oversized lots this close to the Gulf become available. Experience the very best of Anna Maria Island and own your own slice of paradise, where every day feels like a vacation. Come live the Anna Maria Life!

4 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

Discover the ultimate island retreat just three homes from the sugar-white sands and turquoise waters of the Gulf of Mexico. Situated on an oversized 8,250-square-foot lot, this beautifully appointed 4-bedroom, 3-bath home offers nearly 1,700 square feet of coastal living and features a desirable open floor plan designed for gathering and entertaining. The thoughtfully designed layout includes two spacious ensuite bedrooms, a fun bunk room perfect for younger guests, and plenty of room to relax after a day at the beach. Step outside to your own private tropical oasis. The heated pool invites you to enjoy sunny afternoons and evening swims under the stars, while the expansive backyard offers abundant space for lounging, grilling, and making memories with family and friends. The generous lot size is a rarity on Anna Maria Island and provides a true sense of privacy and room to spread out. Along the side of the home, an outdoor game area creates the perfect setting for friendly competitions and endless entertainment after a day spent on the beach. Ideally located in the heart of Anna Maria Island, you're just a short stroll to the boutiques, restaurants, and vibrant atmosphere of Pine Avenue, as well as the island's world-famous beaches. Whether enjoying spectacular Gulf sunsets, dining at one of the island's favorite eateries, or relaxing poolside with loved ones, this home embodies the laid-back luxury of island living. With a proven history as a successful short-term rental and exceptional investment opportunity, this turnkey property offers the perfect blend of lifestyle and income potential. Rarely do homes on oversized lots this close to the Gulf become available. Experience the very best of Anna Maria Island and own your own slice of paradise, where every day feels like a vacation. Come live the Anna Maria Life!

110 Palm Avenue, Anna Maria

$1,545,000

FINANCING FELL THROUGH BACK ON THE MARKET!!! Welcome to your dream getaway, an adorable bungalow located on the north end of Anna Maria Island, directly across from the beach and a lovely park. This charming 3-bedroom, 3-bathroom home is perfect for a full-time residence, an income-generating rental, or a part-time retreat—all in an unbeatable location. Step inside to discover a welcoming living room with beautiful hardwood floors and delightful beach views, seamlessly connecting to the dining area for an open and inviting layout. The kitchen features wood cabinets, sleek quartz countertops, and stainless steel appliances, along with convenient countertop seating. The spacious primary bedroom includes a cozy sitting area and French doors that frame stunning beach views, complemented by an updated en-suite bathroom with a stylish glass shower. The second bedroom also boasts its own en-suite, providing comfort and privacy for guests. Outside, enjoy your private deck, ideal for sunbathing and grilling, complete with an outdoor shower for rinsing off after a day at the beach. The heated pool offers a refreshing retreat on warm days, while the covered, screened front porch is the perfect spot to relax with morning coffee and take in the serene blue waters. Located close to Pine Avenue’s boutique shops, delightful restaurants, and the picturesque Bean Point, this property features a durable metal roof, hardy board siding, and newer windows, enhancing its appeal and longevity. Don’t miss the chance to make this charming bungalow your own—schedule your showing today and embrace the island lifestyle!

3 Beds ⋅ 3 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

FINANCING FELL THROUGH BACK ON THE MARKET!!! Welcome to your dream getaway, an adorable bungalow located on the north end of Anna Maria Island, directly across from the beach and a lovely park. This charming 3-bedroom, 3-bathroom home is perfect for a full-time residence, an income-generating rental, or a part-time retreat—all in an unbeatable location. Step inside to discover a welcoming living room with beautiful hardwood floors and delightful beach views, seamlessly connecting to the dining area for an open and inviting layout. The kitchen features wood cabinets, sleek quartz countertops, and stainless steel appliances, along with convenient countertop seating. The spacious primary bedroom includes a cozy sitting area and French doors that frame stunning beach views, complemented by an updated en-suite bathroom with a stylish glass shower. The second bedroom also boasts its own en-suite, providing comfort and privacy for guests. Outside, enjoy your private deck, ideal for sunbathing and grilling, complete with an outdoor shower for rinsing off after a day at the beach. The heated pool offers a refreshing retreat on warm days, while the covered, screened front porch is the perfect spot to relax with morning coffee and take in the serene blue waters. Located close to Pine Avenue’s boutique shops, delightful restaurants, and the picturesque Bean Point, this property features a durable metal roof, hardy board siding, and newer windows, enhancing its appeal and longevity. Don’t miss the chance to make this charming bungalow your own—schedule your showing today and embrace the island lifestyle!

317 N Bay Boulevard, Anna Maria

$2,175,000

Spring Avenue. One of Anna Maria Island's most coveted addresses and this elevated pool home does it justice. Located on an island named one of America's prettiest cities by Forbes, this is the kind of home that turns heads before you even walk through the door. Four-car garage plus additional off-street parking front and back means no compromises, whether you're hosting a full house or storing all the toys that come with island life. The open, airy layout with vaulted ceilings and warm wood accents gives you that treehouse-in-the-palms feeling the moment you arrive. Two bedrooms open directly to a private back deck. The pool is your backyard centerpiece. Stroll to Pine Avenue for coffee, dinner, and boutique shopping. Catch the free island trolley at the corner. The Gulf and the Bay are both within easy reach and you are centered between them. No HOA. Weekly rentals permitted. Turnkey furnished. Whether this becomes your primary island escape or a high-performing vacation rental, the bones, the location, and the lifestyle are already here waiting.

3 Beds ⋅ 2 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

Spring Avenue. One of Anna Maria Island's most coveted addresses and this elevated pool home does it justice. Located on an island named one of America's prettiest cities by Forbes, this is the kind of home that turns heads before you even walk through the door. Four-car garage plus additional off-street parking front and back means no compromises, whether you're hosting a full house or storing all the toys that come with island life. The open, airy layout with vaulted ceilings and warm wood accents gives you that treehouse-in-the-palms feeling the moment you arrive. Two bedrooms open directly to a private back deck. The pool is your backyard centerpiece. Stroll to Pine Avenue for coffee, dinner, and boutique shopping. Catch the free island trolley at the corner. The Gulf and the Bay are both within easy reach and you are centered between them. No HOA. Weekly rentals permitted. Turnkey furnished. Whether this becomes your primary island escape or a high-performing vacation rental, the bones, the location, and the lifestyle are already here waiting.

315 Spring Avenue, Anna Maria

$2,695,000

Named "A Wave From It All" by the sellers, this exceptional coastal property offers high-end finishes and a layout designed for seamless indoor/outdoor living. The outdoor pool area serves as a private tropical oasis, perfect for relaxation. The main residence features three bedrooms, each with a king bed and ensuite bathroom. The kitchen is equipped with a Sub-Zero refrigerator, a Wolf range and microwave, Bosch dishwasher and wine cooler. For ultimate privacy, the primary suite is accessed through a unique bookcase doorway. This home comes furnished and includes original artwork by renowned artists and a beautiful outdoor mural by Chad "Cheeta" Ruis. The property also includes a versatile casita featuring two Murphy beds, a half bath, an office area, a laundry room, and a convenient outdoor shower located just outside the half bath which includes both hot and cold water. A small storage garage is available on-site for bikes and beach gear. Located on the North end, the home is a short walk from Bean Point beaches, Bayfront Park, and the boutiques and dining on Pine Avenue. Additionally, the adjacent 10,600+ sq. ft. parcel at 240 Gladiolus is available for separate purchase. It is currently landscaped to enhance the estate and includes a large garage. Don't miss out on this unique opportunity and schedule your private showing today!

4 Beds ⋅ 4 Baths ⋅ Luana Isles SubDv. ⋅ 34216 Zip Code

Named "A Wave From It All" by the sellers, this exceptional coastal property offers high-end finishes and a layout designed for seamless indoor/outdoor living. The outdoor pool area serves as a private tropical oasis, perfect for relaxation. The main residence features three bedrooms, each with a king bed and ensuite bathroom. The kitchen is equipped with a Sub-Zero refrigerator, a Wolf range and microwave, Bosch dishwasher and wine cooler. For ultimate privacy, the primary suite is accessed through a unique bookcase doorway. This home comes furnished and includes original artwork by renowned artists and a beautiful outdoor mural by Chad "Cheeta" Ruis. The property also includes a versatile casita featuring two Murphy beds, a half bath, an office area, a laundry room, and a convenient outdoor shower located just outside the half bath which includes both hot and cold water. A small storage garage is available on-site for bikes and beach gear. Located on the North end, the home is a short walk from Bean Point beaches, Bayfront Park, and the boutiques and dining on Pine Avenue. Additionally, the adjacent 10,600+ sq. ft. parcel at 240 Gladiolus is available for separate purchase. It is currently landscaped to enhance the estate and includes a large garage. Don't miss out on this unique opportunity and schedule your private showing today!

242 Gladiolus Street, Anna Maria

$1,424,000

**NEW PRICE! $1,424,000 | PRIME NORTH END ANNA MARIA ISLAND LOCATION | 8,350 SQ. FT. LOT | REDEVELOPMENT OPPORTUNITY | WEEKLY RENTALS PERMITTED | ARTESIAN WELL!** **LOCATION IS EVERYTHING, AND THIS ONE IS HARD TO BEAT! * Welcome to 306 Palm Avenue, an incredible opportunity to own a piece of paradise in one of the most sought-after locations on Anna Maria Island! Situated on the island's highly desirable NORTH END, just a short stroll from the breathtaking beaches and the charming shops, restaurants, and boutiques of Pine Avenue, this property offers the location, lot size, and potential that buyers dream about! Sitting on an approximately **8,350-square-foot (.19-acre) lot**, this property presents an exceptional opportunity for investors, builders, or buyers looking to create their very own island retreat. Whether you're envisioning a stunning new coastal home, a complete transformation of the existing residence, or a vacation getaway with income-producing potential, the possibilities are exciting! The existing 3-bedroom, 3-bathroom home offers approximately 1,902 square feet of living space, including a separate mother-in-law suite configuration, providing an opportunity to explore a variety of renovation options. **ONE OF THE PROPERTY'S MOST UNIQUE FEATURES IS ITS SEPARATELY DEEDED ARTESIAN WELL!** A distinctive feature that sets this property apart, offering a potential water source for irrigation and landscaping, subject to verification of its condition and permitted uses. The property's well reportedly provides irrigation water to the nearby community center, making it a distinctive part of this north-end property. Imagine creating your own lush tropical oasis with beautiful palms, vibrant landscaping, and an inviting outdoor living space! This property can be sold with or without the well! **WEEKLY RENTALS ARE PERMITTED**, adding another layer of opportunity for those considering a vacation home or investment property. With the Gulf beaches just moments away and the shopping, dining, and old-Florida charm of Pine Avenue nearby, this is the kind of location that makes Anna Maria Island so desirable. The existing home sustained flooding during the 2024 hurricanes and requires substantial renovation, making this an ideal opportunity for buyers ready to bring their contractor, architect, and imagination. A newer metal roof installed in 2024 is already in place, offering an additional feature for those considering renovation. **NOW OFFERED AT $1,424,000 — A $271,000 REDUCTION FROM THE ORIGINAL ASKING PRICE!** Opportunities to secure a sizable lot in this coveted north-end location don't come along every day. Whether your vision is to renovate, reimagine, or explore new construction, 306 Palm Avenue is your chance to create something truly special on Anna Maria Island! **DON'T JUST BUY A HOUSE — CREATE YOUR OWN PIECE OF PARADISE!**

3 Beds ⋅ 3 Baths ⋅ Bimini Bay Colony Club Sub SubDv. ⋅ 34216 Zip Code

**NEW PRICE! $1,424,000 | PRIME NORTH END ANNA MARIA ISLAND LOCATION | 8,350 SQ. FT. LOT | REDEVELOPMENT OPPORTUNITY | WEEKLY RENTALS PERMITTED | ARTESIAN WELL!** **LOCATION IS EVERYTHING, AND THIS ONE IS HARD TO BEAT! * Welcome to 306 Palm Avenue, an incredible opportunity to own a piece of paradise in one of the most sought-after locations on Anna Maria Island! Situated on the island's highly desirable NORTH END, just a short stroll from the breathtaking beaches and the charming shops, restaurants, and boutiques of Pine Avenue, this property offers the location, lot size, and potential that buyers dream about! Sitting on an approximately **8,350-square-foot (.19-acre) lot**, this property presents an exceptional opportunity for investors, builders, or buyers looking to create their very own island retreat. Whether you're envisioning a stunning new coastal home, a complete transformation of the existing residence, or a vacation getaway with income-producing potential, the possibilities are exciting! The existing 3-bedroom, 3-bathroom home offers approximately 1,902 square feet of living space, including a separate mother-in-law suite configuration, providing an opportunity to explore a variety of renovation options. **ONE OF THE PROPERTY'S MOST UNIQUE FEATURES IS ITS SEPARATELY DEEDED ARTESIAN WELL!** A distinctive feature that sets this property apart, offering a potential water source for irrigation and landscaping, subject to verification of its condition and permitted uses. The property's well reportedly provides irrigation water to the nearby community center, making it a distinctive part of this north-end property. Imagine creating your own lush tropical oasis with beautiful palms, vibrant landscaping, and an inviting outdoor living space! This property can be sold with or without the well! **WEEKLY RENTALS ARE PERMITTED**, adding another layer of opportunity for those considering a vacation home or investment property. With the Gulf beaches just moments away and the shopping, dining, and old-Florida charm of Pine Avenue nearby, this is the kind of location that makes Anna Maria Island so desirable. The existing home sustained flooding during the 2024 hurricanes and requires substantial renovation, making this an ideal opportunity for buyers ready to bring their contractor, architect, and imagination. A newer metal roof installed in 2024 is already in place, offering an additional feature for those considering renovation. **NOW OFFERED AT $1,424,000 — A $271,000 REDUCTION FROM THE ORIGINAL ASKING PRICE!** Opportunities to secure a sizable lot in this coveted north-end location don't come along every day. Whether your vision is to renovate, reimagine, or explore new construction, 306 Palm Avenue is your chance to create something truly special on Anna Maria Island! **DON'T JUST BUY A HOUSE — CREATE YOUR OWN PIECE OF PARADISE!**

306 Palm Avenue, Anna Maria

$1,500,000

One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION $100,000...Allowing You Endless Possibilities for Improvements. Welcome to the highly sought after North end of Anna Maria Island. Just steps away from the Morning Sunrise or Evening Sunsets, Take your Pick. This 2 Bed / 2 Bath Island Home Features an Open Floor Plan, Spacious Kitchen, Front & Back Balconies, Large Fenced Back Yard and Ample Parking Both Under House and Extended Driveway. Use your creativity to convert the large open 1st floor workshop into your Personal Space, Home Office, or Outdoor Entertaining Venue. The large backyard can easily accommodate a Pool, Putting Green, Bocci Ball Court, or whatever suites your fancy. Excellent vacation rental income opportunity as well. A perfect combination of Island comfort. A short walk to the Anna Maria City Beach and the bustling offering of shops & dining venues on Pine Avenue. Not to mention the soon to be completed, (October 2026), Anna Maria Island City Pier. "PIERADISE" will feature an Open-Air Neighborhood Bar & Grill, Bait & Tackle Shop and Open Dock Fishing. Island Living at its Best with Great Rental Income Potential Option. This one is definitely worth a visit. Call today to schedule your private showing.

2 Beds ⋅ 2 Baths ⋅ Anna Maria Beach SubDv. ⋅ 34216 Zip Code

One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION $100,000...Allowing You Endless Possibilities for Improvements. Welcome to the highly sought after North end of Anna Maria Island. Just steps away from the Morning Sunrise or Evening Sunsets, Take your Pick. This 2 Bed / 2 Bath Island Home Features an Open Floor Plan, Spacious Kitchen, Front & Back Balconies, Large Fenced Back Yard and Ample Parking Both Under House and Extended Driveway. Use your creativity to convert the large open 1st floor workshop into your Personal Space, Home Office, or Outdoor Entertaining Venue. The large backyard can easily accommodate a Pool, Putting Green, Bocci Ball Court, or whatever suites your fancy. Excellent vacation rental income opportunity as well. A perfect combination of Island comfort. A short walk to the Anna Maria City Beach and the bustling offering of shops & dining venues on Pine Avenue. Not to mention the soon to be completed, (October 2026), Anna Maria Island City Pier. "PIERADISE" will feature an Open-Air Neighborhood Bar & Grill, Bait & Tackle Shop and Open Dock Fishing. Island Living at its Best with Great Rental Income Potential Option. This one is definitely worth a visit. Call today to schedule your private showing.

517 Spring Avenue, Anna Maria

$1,799,900

Location! Location! Location! TRY BEFORE YOU BUY!!** Come Visit…Fall in Love with luxury beach living at it’s finest in this amazing, turnkey furnished, completely and beautifully remodeled 3 bedroom, 3 bathroom resort like pool home with lush island tropical landscaping. This exquisite cottage is nestled on a quiet palm tree lined street, just north of Pine Avenue, in the highly desirable city of Anna Maria, only three houses from the Bay Beach and City Pier!! This is a wonderful investment opportunity, currently showcased as a vacation rental, but could easily be enjoyed as a primary residence or secondary home for our welcomed “snow birds.” This open~ airy~ split floor plan effortlessly combines the seamless living areas of the kitchen, living room, and dining rooms. The updated, beautifully appointed kitchen is sure to impress even the most discerning chef, featuring coastal shaker wood cabinets, glass tile backsplash, stainless appliances, quartzite counter tops, and spacious island with ample seating and storage, illuminated by the beautiful glass pendant lighting above. The stunning formal dining room, with it’s gorgeous, expansive 21 ft sliding glass impact doors overlook the extremely spacious screened lanai and the breathtaking views of the spectacular resort-like pool~spa oasis. Enjoy abundant seating in the spacious living room with sleeper sofa, while watching your favorite movie on the large screen TV above the beautiful electric fireplace. After an enjoyable day at the beach or dinner at one of the many wonderful island restaurants, retreat to the serene primary king en-suite with walk-in shower. The second bedroom offers plenty of space with two twin beds. Impressive third bedroom presents a secondary king en-suite with vaulted ceilings, walk-in shower, private entrance, and is on the alternate side of the home for welcomed privacy. Indulge in the epitome of aquatic luxury with a meticulously crafted pool, complete with state-of-the-art heating and cooling systems, fiber optics, offering a symphony of color and ambiance. The tropical pool oasis is adorned by the captivating centerpiece, the hand crafted giant sea turtle sculpture that was painted by a local artist and previously hung in Mote Marine Aquarium in Sarasota. Enjoy peace of mind with new Hurricane Impact Windows (2022), new Hurricane Impact sliding glass doors (2025), new electrical wiring updated (2025), all new plumbing with new drain lines to the sewer as well as new supply lines (2022), newly built saltwater pool with pebble tech surface-heated and cooled with fiber optic lighting (2023), pool safety alarms (2023), new interior painting (2025), exterior painting (2022), outdoor shower, new landscaping (2023), new A/C (2025), new metal roof (2025)… too many updates to list! Extensive updates list available upon request. Enjoy all that Anna Maria has to provide with it’s nearby City Pier, beautiful world famous beaches, swimming, boating, fishing, abundant island boutiques and shops, plus wonderful island restaurants for your dining pleasure. Enjoy watching the enticing virtual tour and call today!! **If you book a stay as a guest and decide to buy, you will have your net rental refunded with an accepted contract at the Closing of Escrow. Subject to availability. Maximum rental 7 days. Based on NET rental rate. Cleaning, taxes & fees apply.

3 Beds ⋅ 3 Baths ⋅ Lake La Vista Sub SubDv. ⋅ 34216 Zip Code

Location! Location! Location! TRY BEFORE YOU BUY!!** Come Visit…Fall in Love with luxury beach living at it’s finest in this amazing, turnkey furnished, completely and beautifully remodeled 3 bedroom, 3 bathroom resort like pool home with lush island tropical landscaping. This exquisite cottage is nestled on a quiet palm tree lined street, just north of Pine Avenue, in the highly desirable city of Anna Maria, only three houses from the Bay Beach and City Pier!! This is a wonderful investment opportunity, currently showcased as a vacation rental, but could easily be enjoyed as a primary residence or secondary home for our welcomed “snow birds.” This open~ airy~ split floor plan effortlessly combines the seamless living areas of the kitchen, living room, and dining rooms. The updated, beautifully appointed kitchen is sure to impress even the most discerning chef, featuring coastal shaker wood cabinets, glass tile backsplash, stainless appliances, quartzite counter tops, and spacious island with ample seating and storage, illuminated by the beautiful glass pendant lighting above. The stunning formal dining room, with it’s gorgeous, expansive 21 ft sliding glass impact doors overlook the extremely spacious screened lanai and the breathtaking views of the spectacular resort-like pool~spa oasis. Enjoy abundant seating in the spacious living room with sleeper sofa, while watching your favorite movie on the large screen TV above the beautiful electric fireplace. After an enjoyable day at the beach or dinner at one of the many wonderful island restaurants, retreat to the serene primary king en-suite with walk-in shower. The second bedroom offers plenty of space with two twin beds. Impressive third bedroom presents a secondary king en-suite with vaulted ceilings, walk-in shower, private entrance, and is on the alternate side of the home for welcomed privacy. Indulge in the epitome of aquatic luxury with a meticulously crafted pool, complete with state-of-the-art heating and cooling systems, fiber optics, offering a symphony of color and ambiance. The tropical pool oasis is adorned by the captivating centerpiece, the hand crafted giant sea turtle sculpture that was painted by a local artist and previously hung in Mote Marine Aquarium in Sarasota. Enjoy peace of mind with new Hurricane Impact Windows (2022), new Hurricane Impact sliding glass doors (2025), new electrical wiring updated (2025), all new plumbing with new drain lines to the sewer as well as new supply lines (2022), newly built saltwater pool with pebble tech surface-heated and cooled with fiber optic lighting (2023), pool safety alarms (2023), new interior painting (2025), exterior painting (2022), outdoor shower, new landscaping (2023), new A/C (2025), new metal roof (2025)… too many updates to list! Extensive updates list available upon request. Enjoy all that Anna Maria has to provide with it’s nearby City Pier, beautiful world famous beaches, swimming, boating, fishing, abundant island boutiques and shops, plus wonderful island restaurants for your dining pleasure. Enjoy watching the enticing virtual tour and call today!! **If you book a stay as a guest and decide to buy, you will have your net rental refunded with an accepted contract at the Closing of Escrow. Subject to availability. Maximum rental 7 days. Based on NET rental rate. Cleaning, taxes & fees apply.

154 Crescent Drive, Anna Maria

$1,750,000

Welcome to "Birdsong"! Discover the perfect blend of island charm and modern comfort in this beautifully updated 2-bedroom, 2-bath home located in one of Anna Maria Island’s most desirable neighborhoods. Just a 3-minute walk to the pristine Gulf beaches, this property offers the ideal setting for full-time living, a second home, or a high-performing investment. Step inside to an inviting open-concept layout featuring bright coastal décor, tile flooring throughout, and a seamless flow from the living area to the well-appointed kitchen with stainless steel appliances, granite countertops, and ample storage. Retreat to the serene primary suite with its private bath, while guests enjoy a comfortable second bedroom and full bathroom. Outdoors, your private oasis awaits—complete with a sparkling saltwater pool, lush tropical landscaping, and multiple lounging areas perfect for relaxing after a day at the beach. With established successful vacation rental performance, this home comes turnkey-ready for immediate enjoyment or continued income generation.

2 Beds ⋅ 2 Baths ⋅ Shore Acres SubDv. ⋅ 34216 Zip Code

Welcome to "Birdsong"! Discover the perfect blend of island charm and modern comfort in this beautifully updated 2-bedroom, 2-bath home located in one of Anna Maria Island’s most desirable neighborhoods. Just a 3-minute walk to the pristine Gulf beaches, this property offers the ideal setting for full-time living, a second home, or a high-performing investment. Step inside to an inviting open-concept layout featuring bright coastal décor, tile flooring throughout, and a seamless flow from the living area to the well-appointed kitchen with stainless steel appliances, granite countertops, and ample storage. Retreat to the serene primary suite with its private bath, while guests enjoy a comfortable second bedroom and full bathroom. Outdoors, your private oasis awaits—complete with a sparkling saltwater pool, lush tropical landscaping, and multiple lounging areas perfect for relaxing after a day at the beach. With established successful vacation rental performance, this home comes turnkey-ready for immediate enjoyment or continued income generation.

709 Fern Street, Anna Maria

$1,895,000

Virtually Staged. Some photos have been virtually staged. Waterfront living, situated in a peaceful, natural, ”Old Florida” setting , surrounded by tropical seagrapes, palm trees and mangroves this ground-level, canal-lined 3 bedroom, 3 bath property is located in an ideal spot on the north end of Anna Maria island in the city of Anna Maria. Two blocks to the shops and food on Pine Avenue, three blocks to the Anna Maria trolley stop, four blocks to the white sand of Coconut Avenue beach on the Gulf of Mexico, five blocks to the Anna Maria city pier and a seven minute idle boat ride from your dock in back to Tampa Bay. Very walkable/bikeable as there are ten restaurants within eight blocks. A sunny, open concept interior with windows that bring the outside in. New appliances, new AC, new water heater, new flooring, new kitchen cabinets with a beverage cooler and quartz counter tops. Freshly painted and wallpapered with big bedrooms and a comfortably large master bedroom with His and Her bathrooms. Three bathrooms total, two with showers and one with a bathtub. Canal side sunroom with a cozy, elevated fireplace for those cool days and a detached two car garage that has more living space potential. On the mangrove-lined canal is an 8’x24’ dock with room for your boat and plenty of room to entertain. Look for the manatees gliding by and watch for the flying wild-eyed mullet. Maybe a dolphin will pop up! House is also on a dead-end street for added protection and does not attract beach day-trip parkers. Plenty of room for a pool or two. Come take a look at the perfect spot to enjoy Anna Maria.

3 Beds ⋅ 3 Baths ⋅ Island Cedars SubDv. ⋅ 34216 Zip Code

Virtually Staged. Some photos have been virtually staged. Waterfront living, situated in a peaceful, natural, ”Old Florida” setting , surrounded by tropical seagrapes, palm trees and mangroves this ground-level, canal-lined 3 bedroom, 3 bath property is located in an ideal spot on the north end of Anna Maria island in the city of Anna Maria. Two blocks to the shops and food on Pine Avenue, three blocks to the Anna Maria trolley stop, four blocks to the white sand of Coconut Avenue beach on the Gulf of Mexico, five blocks to the Anna Maria city pier and a seven minute idle boat ride from your dock in back to Tampa Bay. Very walkable/bikeable as there are ten restaurants within eight blocks. A sunny, open concept interior with windows that bring the outside in. New appliances, new AC, new water heater, new flooring, new kitchen cabinets with a beverage cooler and quartz counter tops. Freshly painted and wallpapered with big bedrooms and a comfortably large master bedroom with His and Her bathrooms. Three bathrooms total, two with showers and one with a bathtub. Canal side sunroom with a cozy, elevated fireplace for those cool days and a detached two car garage that has more living space potential. On the mangrove-lined canal is an 8’x24’ dock with room for your boat and plenty of room to entertain. Look for the manatees gliding by and watch for the flying wild-eyed mullet. Maybe a dolphin will pop up! House is also on a dead-end street for added protection and does not attract beach day-trip parkers. Plenty of room for a pool or two. Come take a look at the perfect spot to enjoy Anna Maria.

120 Hammock Road, Anna Maria

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