Longboat Key Homes with Florida Architectural style

Longboat Key Homes with Florida Architectural style

Welcome to Longboat Key, Florida – a slice of paradise nestled along the stunning Gulf Coast. This idyllic barrier island is renowned for its pristine beaches, vibrant sunsets, and a laid-back lifestyle that perfectly captures the essence of coastal living. With its charming blend of natural beauty and upscale amenities, Longboat Key is a sought-after destination for those looking to embrace the Florida lifestyle.

Longboat Key boasts a rich tapestry of Florida architectural styles, characterized by their seamless integration with the surrounding environment. Here, you’ll find exquisite homes that reflect the essence of tropical living, featuring open floor plans, expansive windows, and lush landscaping. Many properties showcase the classic elements of Mediterranean Revival and Contemporary designs, complete with terracotta roofs, stucco exteriors, and large outdoor spaces perfect for entertaining or simply soaking in the sun.

The community is home to a diverse range of properties, from luxurious beachfront estates to charming villas tucked away in serene neighborhoods. Whether you’re seeking a year-round residence or a seasonal getaway, Longboat Key offers an array of options to suit every lifestyle.

In addition to its stunning real estate, Longboat Key is known for its exceptional recreational opportunities, including world-class golf courses, fine dining, and boutique shopping. With easy access to nearby Sarasota, residents can enjoy a vibrant cultural scene, including art galleries, theaters, and festivals.

Discover the enchanting allure of Longboat Key, where every day feels like a vacation, and your dream home awaits amidst the beauty of Florida’s Gulf Coast.

Newest Longboat Key Homes with Florida Architectural style

$589,000
2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv. ⋅ 34228 Zip Code
There is a certain ease to life on Longboat Key, where mornings can begin with a walk to the beach, afternoons unfold by the pool or on the tennis court, and dinner beside the water is never far from home. Set within Cedars East at Cedars Tennis Resort & Club, this beautifully maintained three-level townhome offers a refined way to experience one of Florida’s most desirable barrier-island lifestyles. Natural light is one of the first things you notice. An abundance of windows fills the home with sunshine, creating a bright, calm, and serene atmosphere that feels perfectly suited to its coastal surroundings. New luxury vinyl plank flooring extends through the entry and main living level, giving the home a fresh, cohesive look, while carpeting along the staircase and throughout the third-floor bedroom level adds warmth and comfort to the private spaces. The second floor brings the kitchen, dining, and living areas together in an easy, welcoming flow designed for relaxed everyday living and effortless entertaining. Just beyond the living room, the screened balcony creates a peaceful outdoor retreat for morning coffee, casual dining, quiet reading, or unwinding at the end of the day. A convenient half bath completes this level. Upstairs, the primary suite offers a private ensuite bath with dual sinks and a comfortable sense of separation from the main living areas. The second bedroom features a walk-in closet and is positioned near the full guest bath and upstairs laundry closet. The washer and dryer are approximately three months old and are included with the home. Thoughtful improvements add both style and confidence, including a roof replaced in 2024, a 2024 HVAC system serviced in April 2026, updated interior paint, refreshed flooring, newer toilets, faucets, light fixtures and vents, and a new garage door. Garage parking adds welcome convenience along with room for bicycles, beach equipment, and additional storage. Life at Cedars Tennis Resort & Club is centered around the outdoors and the relaxed sophistication of Longboat Key. Enjoy tennis and pickleball, spend the afternoon by the heated community pool, stay active in the fitness facilities, or gather for a meal without leaving the neighborhood. Nearby beach access makes Gulf days easy to enjoy, while waterfront restaurants, island cafés, marinas, biking routes, and the natural beauty of Longboat Key are all close at hand. For buyers considering investment potential, the property has a strong short-term rental history and is already heavily booked from December through June 2027, offering the advantage of established demand and reservations already in place. All rentals remain subject to current association rules, approval requirements, and the terms of existing reservations. From fresh seafood and sunset dinners to quiet mornings near the shore, this location places the best of Longboat Key within easy reach. St. Armands Circle, Anna Maria Island, and the cultural attractions of Sarasota are also nearby, allowing you to enjoy the island’s peaceful atmosphere without feeling removed from everything the area has to offer. Whether envisioned as a full-time residence, seasonal retreat, or income-producing coastal getaway, this is an opportunity to enjoy thoughtful updates, abundant natural light, resort-inspired amenities, garage parking, and the unmistakable lifestyle of Longboat Key. ¤ Please see 3D Tour and Video ¤

508 Forest Way Unit 508, Longboat Key
$425,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.

4390 Exeter Drive Unit 107, Longboat Key
$1,999,000
5 Beds ⋅ 3 Baths ⋅ Country Club Shores SubDv. ⋅ 34228 Zip Code
Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front home offers the rare opportunity to pick up where the current owner left off—finishing a sophisticated coastal residence with the majority of major structural work already completed. For discerning buyers seeking to capture immediate equity and create a bespoke waterfront retreat, this property represents outstanding value in prime Longboat Key real estate. Set on a spacious 110’ x 110’ canal-front lot, the home features a fully reconstructed seawall and a private dock equipped with a 13,000-pound Platinum Series boat lift, providing effortless access to Sarasota Bay and the sparkling Gulf of Mexico. The residence is framed for approximately 3,089 square feet under air, offering 5 bedrooms and 3 bathrooms in an elegant coastal ranch-style layout designed for seamless indoor-outdoor living. Substantial improvements have already been executed to the highest standards: a brand-new roof, complete framing, exterior walls, plumbing and electrical rough-ins, natural gas lines, insulation, HVAC ductwork, and impact-resistant windows and doors. Premium materials and finishes—including custom Italian cabinetry, Miele appliances, designer fixtures, and additional high-end components—convey with the property. Engineer-prepared plans provide a clear roadmap for completion, empowering the next owner to personalize the final touches while benefiting from the extensive work already invested. Located in one of the best positions within the desirable Country Club Shores community, this fixer-upper presents the perfect canvas to realize the seller’s vision of an amazing luxury waterfront home. Imagine waking to serene water views, launching your boat from your private dock, and enjoying the effortless Florida lifestyle that defines Longboat Key. Just moments away, enjoy world-class amenities and recreation: championship golf at the prestigious Longboat Key Club, pristine Gulf beaches for sun-soaked days, and the vibrant dining and shopping scene at St. Armands Circle. Explore Sarasota’s renowned fine and performing arts venues, upscale boutiques, and waterfront restaurants—all while residing in this sought-after enclave. Whether you crave boating adventures, cultural experiences, or relaxed coastal living, this location delivers unparalleled convenience and luxury. Don’t miss this unique opportunity to complete a standout waterfront property and unlock its full potential in one of Florida’s most desirable communities.

525 Sloop Lane, Longboat Key
$950,000
3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv. ⋅ 34228 Zip Code
Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

2350 Harbour Oaks Drive, Longboat Key
$569,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
If you are looking for a tastefully upgraded Longboat Key beach house, this is it! Relax in your completely renovated coastal-contemporary, stand-alone villa, with its front pond view, private rear patio and large yard space. The uncrowded, 11-mile Longboat Key beach is directly across Gulf of Mexico Drive via Spanish Main's private deeded access. Your spacious, light-filled home welcomes you with a charming entrance foyer, open living-dining room with built-in cabinets and a large kitchen-family room area with sliding doors to the rear yard. Your bright kitchen has an island, new appliances, quartz counters, and wood cabinets with lots of storage space. Important additional benefits include a new electric hot water tank, new hurricane rated doors and rear sliders, tile roof replaced in 2017, flat roof in 2024, impact windows in 2020 and 2024, and A/C in 2022. The primary bedroom has a walk-in closet and an en suite bath with a new walk-in shower and vanity. The guest bedroom has a view of the pond and double closets. The guest bathroom has a skylight and a new walk-in shower, vanity, linen and medicine cabinets. If you want to move right in or rent it, the attractive turn-key furnishings are negotiable. Outside, there is a large side storage area for bicycles and beach toys. The front porch offers a tranquil area to relax and view the large pond with its ducks, jumping fish, and pretty night lights. Walk, bike or drive to the heated community pool, patio area, and clubhouse adjacent to the deep water marina and kayak launch. If you are a boat person, slips can be rented, as available, for an extremely reasonable cost and there is easy access to Sarasota bay and the Intracoastal Waterway with no fixed bridges. Spanish Main Yacht Club is an over-55 community, conveniently located near several restaurants, Durante Park, community tennis, pickle-ball, dog park, fitness activities and St. Armands Circle shops and restaurants. Let me show you the lifestyle that this beautiful, unique villa has to offer.

524 Spanish Drive S Unit 125, Longboat Key
$307,000
1 Beds ⋅ 1 Baths ⋅ Longboat Harbour Towers SubDv. ⋅ 34228 Zip Code
Price Improved! Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features Hurricane-Impact Sliding Glass Doors &Windows( over $40 Value) allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a Private Beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, plus more ..and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value. Don't Waite! Schedule your private virtual viewing today.

4350 Chatham Drive Unit 105, Longboat Key
$499,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
The lifestyle stays premium. The price just got friendlier. Tucked within the waterfront community of Spanish Main Yacht Club on the north end of Longboat Key, this fully renovated detached villa offers a timeless coastal flair just steps from the beach. A true hidden gem and slice of paradise, residents enjoy private deeded beach access to the Gulf of America, a deep water marina with affordable boat slips, and the ultimate boating lifestyle with easy access to waterfront restaurants and open waters. This light and bright 2-bedroom, 2-bath residence is being offered turnkey furnished. Featuring an open floorplan with luxury vinyl plank flooring, impact windows and doors, custom window shades throughout, and a spacious Florida room ideal for additional living or entertaining space. The beautifully updated kitchen showcases quartz countertops, stainless steel appliances, abundant custom cabinetry with soft-close drawers, and a large seating island perfect for gathering. Additional highlights include an interior laundry room with stackable washer and dryer, water softener system, stone paver patio, covered parking, and private driveway. Spanish Main Yacht Club is a vibrant and active 55+ community offering a heated waterfront pool, shuffleboard, social events, pet-friendly policies, maintenance-free living, and one of the most desirable 40-slip marinas on Longboat Key. Ideally located just minutes from St. Armands Circle, Sarasota, and Anna Maria Island, this exceptional Longboat Key retreat is ready for immediate enjoyment.

546 Spanish Drive S, Longboat Key
$1,899,000
4 Beds ⋅ 3 Baths ⋅ Triton Cove SubDv. ⋅ 34228 Zip Code
Welcome to island living on Longboat Key, one of Sarasota's premier barrier island destinations. In Triton Cove, this coastal residence offers direct Gulf Beach access across the street and a lifestyle designed for boating, seasonal use or year-round living along Florida's Gulf Coast. Enjoy nightly sunsets along Gulf of Mexico Drive or experience world-class dining and shopping on nearby St. Armands Circle. An elevated entry leads to the main living level, where expansive glass defines the open-concept design, connecting the living room, kitchen and dining areas. Positioned within a five-residence enclave, this property offers convenient access to Sarasota dining, shopping and waterfront recreation while supporting a low-maintenance ownership experience. This tri-level single-family home features four bedrooms and 2.5 baths, complemented by a two-car garage with dual 8-foot doors and extensive storage. The ground level includes multiple flexible-use rooms ideal for fitness, storage or organization of beach equipment, kayaks, bicycles and boating gear. A dumbwaiter provides direct access from the garage to the kitchen. Interior features include engineered wood flooring in main living areas and new carpet in bedrooms. The kitchen is designed with wood cabinetry, granite countertops, deep storage drawers, an appliance garage, a rollout pantry wall and stainless steel appliances, including a GE wall oven/microwave combo, an induction cooktop and an LG refrigerator. Additional features include a wet bar with cabinetry and a mirrored wall, an electric fireplace and plantation shutters. The primary suite offers a private setting with dual vanities, a soaking tub, a separate shower, two walk-in closets and a Juliette balcony with partial gulf views. The third level includes a bonus room suitable for media, an office or a private retreat. Outdoor living includes a natural gas-heated pool and spa, an outdoor shower and a private fenced setting. Pool systems including a new motor, filters and heater, and the interior of the pool has been refinished. Recent improvements include a 2024 shingle roof with warranty, zoned HVAC systems installed in 2018 and 2020, and a 2025 water heater. The home includes a monitored alarm system. Triton Cove offers a maintained environment with low monthly HOA fees of $500, including landscape maintenance of common areas, pest control, pool service and exterior lighting. Leasing is permitted up to four times annually with a one-month minimum. Located near Longboat Key Bayfront Park and Longboat Dog Park, residents may enjoy pickleball, tennis, playgrounds and picnic areas. Nearby conveniences include grocery, pharmacy, boat rentals and storage options along Longboat Key, as well as being within reach of Sarasota amenities. Optional membership to the Longboat Key Club provides access to golf, tennis, beach and social amenities, enhancing the gulf-front lifestyle experience on Florida's west coast. Don’t miss out on your private tour of this special coastal home featuring four bedrooms, 3000-plus square feet of air-conditioned living space, a two-car garage, a 30-foot pool and a hot tub on Longboat Key with beach access with low taxes for under $2 million; this is an extraordinary value!

3040 Gulf Of Mexico Drive Unit 3, Longboat Key
$324,000
1 Beds ⋅ 1 Baths ⋅ Neptune On Longboat Key SubDv. ⋅ 34228 Zip Code
A renovated condo directly across from public beach access under $350,000. on Longboat Key? This is the one you've been looking for! Perfectly positioned for both personal enjoyment and strong rental income potential. Whether you're seeking a low-maintenance vacation escape or an income-generating property, this location checks all the boxes. Walk across the street to watch sunset on the sand, then stroll to Publix, Bayfront Park's tennis & pickleball courts, the library, or one of the island’s cozy dining spots. Everything your guests—or you—could want is right at your doorstep. The unit features a bright, open living space with tile flooring, a spacious bedroom, walk-in closet and parking. The well-maintained community offers low HOA fees and a relaxing island vibe that keeps guests coming back. Don’t miss out on this rare opportunity to own on Longboat Key—whether you're investing in your future or your lifestyle.

2850 Gulf Of Mexico Drive Unit 5, Longboat Key
$599,000
2 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code
Enjoy the benefits of a well-managed waterfront community with just 39 residences and attractively low condominium association fees. Set within an intimate waterfront enclave, this Bay Harbour retreat captures the essence of refined island living. Framed by swaying palms and 720 feet of shimmering Sarasota Bay frontage, the community feels like a private tropical sanctuary, where beautiful sunrises paint the sky and waterfowl dive gracefully for fish along the shoreline. Boaters will appreciate the ideal marina location, offering a quick, scenic ride to the Gulf of Mexico. The marina is fully equipped with electrical service, fresh water and a fish-cleaning station, while the seawall provides front-row views of dolphins and playful manatees. A kayak launch adds even more ways to enjoy life on the water. Inside, this spacious two-bedroom, two-bath residence spans 1,300-plus square feet of light-filled living with captivating views of Bay Harbour Marina and Sarasota Bay. Both bedrooms feature walk-in closets, and the kitchen blends style and function with wood cabinetry with glass fronts, stainless-steel appliances, solid-surface countertops and tile flooring throughout. The generous primary suite offers an en-suite bath and a peaceful vantage point overlooking the turquoise bay waters. Offered furnished, the home includes an in-unit washer and dryer, covered assigned parking, ample guest parking and elevator access. Bay Harbour’s amenities elevate the experience with a heated pool, grilling area and first-come boat slips accommodating vessels up to 42 feet. Owners may have one pet. Positioned in south Longboat Key, you’re just 15 minutes from downtown Sarasota, home to upscale shopping, acclaimed dining, galleries, theater, opera, ballet and vibrant arts scene. And for everyday indulgence, you can visit or bike to St. Armands Circle, a beloved destination of boutiques, cafés and coastal charm.

448 Gulf Of Mexico Drive Unit A205, Longboat Key
$750,000
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
$1,795,000
3 Beds ⋅ 3 Baths ⋅ Emerald Harbor SubDv. ⋅ 34228 Zip Code
Exceptional opportunity to own a Longboat Key waterfront home in the highly desired community of Emerald Harbor. This 3BR/2BA, 1,926-sf canal front home with pool sits on an oversized 100x155-ft lot along one of Longboat’s widest canals (~110 ft) offering deep-water boating access just a half mile to the Intracoastal Waterway. Private beach access with parking is less than half a mile away. The property experienced storm-related water damage in 2024 and is ready for renovation or a brand-new custom home build. Enjoy island living close to The St. Regis Longboat Key Resort, The Resort at Longboat Key Club, St. Armands Circle, and North Longboat Village favorites—Shore, Mar Vista, Whitney’s, and Lazy Lobster. Emerald Harbor Longboat Key home for sale combines boating, beach access, and the ultimate Florida lifestyle—an unbeatable fixer-upper Longboat Key canal-front opportunity in one of the island’s premier neighborhoods.

741 Old Compass Road, Longboat Key
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