Location: Longboat Key
Do Not Show Listings
455 LONGBOAT CLUB RD #402, LONGBOAT KEY, FL 34228
$2,095,00056 Days on yellowkey MLS ID: A4686984
REDUCED by $100,000 (4.6%) on 05/04/2026
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2410 Built: 1990 Tax: $18,228 (2025)Community: PierreSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$18,228
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Gulf-front living takes on a refined sense of scale in this beautifully renovated residence at The Pierre, an intimate waterfront community of just 66 residences set behind the gates of the Longboat Key Club. With 2,400+ sq. ft. of thoughtfully updated living space, the residence offers a seamless blend of comfort, style and presence in one of the island’s most desirable locations. From the moment you enter the foyer, the tone is set with diagonal tile flooring, high ceilings, crown molding and tray accents that create a sense of openness and quiet sophistication. The great room unfolds with ease, connecting living, dining and kitchen spaces in a way that supports both everyday living and entertaining. A full wall of glass in the living area draws in natural light and frames views of the Gulf and manicured grounds, while a custom built-in adds both function and visual interest. The dining area sits adjacent, wrapped in glass and oriented toward the view, creating a natural setting for gatherings. The kitchen has been remarkably reimagined with black stone countertops, off-white cabinetry with glass panel accents, high-end appliances and generous counter space with a breakfast bar. A slider opens to the terrace, allowing for easy indoor-outdoor flow. A private office with double glass doors and a tray ceiling with custom lighting provides a quiet and versatile workspace. The primary suite is spacious and serene, featuring a breath taking view, terrace access and a large bath designed with both comfort and flexibility in mind. Dual water closet areas and a distinctive glass-enclosed circular shower with detailed tilework add a unique architectural element. Guest accommodations are well-sized and welcoming, and an in-residence laundry room adds everyday convenience. Residents of The Pierre enjoy a full complement of amenities, including concierge service, under-building parking, 24-hour security, a fitness center, 2 guests suites, heated pool, spa, children’s pool, Har-Tru tennis courts, shuffleboard courts and private beach access. Membership opportunities at the Longboat Key Club offer access to championship golf and fine dining, all within proximity to St. Armands Circle and Sarasota’s vibrant downtown.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
6750 GULF OF MEXICO DR #152, LONGBOAT KEY, FL 34228
$355,00061 Days on yellowkey MLS ID: A4686698
REDUCED by $20,000 (5.3%) on 05/03/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 990 Built: 1970 Tax: $2,215 (2025)Community: Whitney BeachCondo
Taxes:$2,215
Remarks: If you’ve been waiting for the perfect second-floor residence in the highly sought-after Whitney Beach community on Longboat Key, this is the one. Offering some of the finest views in the complex, this turn-key condominium has been thoughtfully upgraded and is move-in ready. What truly sets Whitney Beach apart is its rare combination of resort-style living and relaxed island charm: Pet-friendly paradise — One of the few communities on Longboat Key that welcomes up to two large dogs, making it a dream for dog lovers. Private boat docks on the protected bayou, providing easy access to the water. One of the widest and most beautiful private beaches on the island, with direct deeded access. Resort-style heated and cooled pools for year-round enjoyment. Prime second-floor positioning that delivers the community’s best panoramic views. Unforgettable wildlife moments right from your home — watch mama manatees nurturing their calves in the canal and dolphins feeding just offshore. Convenient kayak storage and launch area. Exceptionally walkable location — just steps from upscale restaurants, shops, and a fitness center. One of the most pedestrian-friendly communities on all of Longboat Key. A thoughtfully designed floor plan with a low-density, intimate feel — no high-rise hotel atmosphere here. Spacious, peaceful surroundings where residents enjoy privacy and breathing room. Serene walking path to the iconic Beer Can Island (Greer Island), with its pristine beach and natural beauty. Just over the bridge lies Coquina Beach, home to vibrant weekly craft fairs and farmers markets. Nestled at the tranquil northern end of Longboat Key, this location offers the best of both worlds — easy proximity to the charming village atmosphere and world-class amenities of Anna Maria Island, one of America’s most treasured coastal gems. Don’t miss your opportunity to own a piece of this turquoise paradise at an exceptional value. Wake up every morning in one of Florida’s most exclusive island retreats — where luxury, nature, and relaxed coastal living come together perfectly.
Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)
Listing Agent: Amy Jones (941-993-9380)
2295 GULF OF MEXICO DR #23S, LONGBOAT KEY, FL 34228
$1,295,000217 Days on yellowkey MLS ID: A4669226
REDUCED by $100,000 (7.2%) on 04/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,812 (2024)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$9,812
Tax Year: 2024
Remarks: Set directly on the shores of the Gulf of Mexico, this beautifully renovated residence in the Islander Club captures the essence of Longboat Key beachfront living. Located in the desirable South Tower, this 2BR/2BA home showcases a fresh coastal design with wide-plank flooring, crown molding, recessed lighting, and an open layout oriented to the water. The kitchen exudes coastal charm with stone countertops, shaker cabinetry, stainless-steel appliances, and a sea-glass tile backsplash. Both baths have been redone with refined finishes, glass-enclosed showers, and clean modern tilework. Floor-to-ceiling sliders open to an expansive covered terrace—perfect for outdoor dining, lounging, and taking in sweeping Gulf views. The primary suite also enjoys terrace access and an endless horizon of turquoise water. Residents of the Islander Club enjoy 400 feet of private beach, a Gulf-front pool, fitness center, tennis courts, pickleball, library, social lounge, and on-site management within two secure towers and gated entry. The recently updated common areas - including the elegant lobby and clubroom - offer a stylish, contemporary ambiance overlooking the Gulf. Ideally positioned near St. Armands Circle and Sarasota’s world-class dining, shopping, and cultural attractions, this residence offers an effortless blend of comfort, sophistication, and beachfront tranquility.
1591 GULF OF MEXICO DR #512, LONGBOAT KEY, FL 34228
$2,400,000224 Days on yellowkey MLS ID: A4668544
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2154 Built: 2024Community: St. Regis Longboat KeyCondo
Taxes:$0
Remarks: Fractional Ownership. Fractional Ownership Opportunity at The St. Regis Longboat Key. Each purchase includes complimentary Resort Membership, valued at $125,000, along with the added benefit of no annual dues (a $14,000 value) and no minimum annual expenditure requirements. The Resort Membership can be enjoyed year-round, providing exceptional value and convenience to owners. For 2025, fee for each 30 day interest is set at $24,785, with an anticipated decrease in 2026. This comprehensive fee covers a wide range of services and expenses, including Condo fees, Property taxes, Utilities, Housekeeping services, Property management, Insurance, Furniture replacement reserve, and Maintenance reserve. This elegant and gracious two-bedroom St. Regis residence is owned by a limited liability company (LLC), offering a distinctive ownership structure where shares are allocated in 30 day segments. Prospective buyers have the opportunity to purchase one or more 30 day segments May through October, with each 30 day segment available at a price of $400,000. This condominium is designed with spacious rooms, expansive glass windows, and soaring ceilings that create an airy and inviting atmosphere. The gourmet kitchen is well-appointed with premium Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, and a side-by-side refrigerator, making it ideal for culinary enthusiasts. The large owner's suite offers a luxurious primary bath featuring double vanities, a deep soaking tub, a frameless walk-in shower, and a private water closet. The residence is being sold fully furnished with pieces from Restoration Hardware. With walls of glass opening to the large wraparound private terrace, owners can host memorable gatherings with stylish furnishings, an outdoor gas grill, and offering stunning views of Sarasota Bayfront. Additional conveniences include a private two-car garage on the first level and easy access to a semi-private elevator that opens directly into the residence. Nestled within the first branded residential community and ultra-luxury five-star resort on the Gulf of Mexico, The Residences at The St. Regis Longboat Key combine legendary service with the tranquil allure of a secluded seaside getaway on Longboat Key, Florida. The community spans over 17 acres and boasts 800 feet of direct beachfront, offering residents an unparalleled lifestyle. Amenities include signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience the finest in fractional luxury living at The St. Regis Longboat Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
2055 GULF OF MEXICO DR #G2-213, LONGBOAT KEY, FL 34228
$622,00076 Days on yellowkey MLS ID: TB8485915
REDUCED by $3,000 (0.5%) on 05/03/2026
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 1094 Built: 1974 Tax: $5,426 (2025)Community: Seaplace ICondo
Taxes:$5,426
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: NO expense spared and everything replaced! Gulf and greenbelt views await from your top floor Seaplace condo! Completely remodeled. This gorgeous gulf-facing oversized one bedroom, 1.5 bath end unit with vaulted ceilings features 1,094 square feet of living space and spacious lanai adding an additional 112 square feet with custom 95% UV blocking solar shades. The convenient second floor location provides quick access to the beach, which is only 178 yards from your front door. Enjoy beautiful sunsets with a glass of wine, while taking in the peaceful greenbelt and gulf views from your screened-in lanai complete with high quality Polywood outdoor furniture and Modern Forms WIFI enabled ceiling fan. The spectacular remodel includes new hurricane impact sliding glass doors and bedroom window, new front door and casement window, HVAC unit replaced in 2022, LG Thin Q stacked washer and dryer, ceiling fans in bedroom and living room, Nest programable WIFI thermostat, all new plumbing and plumbing fixtures, all electrical replaced including electrical outlets, new switches and LED recessed lighting throughout. The new porcelain plank "driftwood look" floor tiles throughout the condo and into the Lanai compliment the coastal, beachy vibe of the Cypress Pecky Wood and shiplap accent walls. The gourmet kitchen was completely redesigned with an open concept and includes Kraftmaid soft close wood cabinetry and drawers, GE Cafe appliances suite with convection oven, warming drawer and conduction cooktop, floating shelves and Cambria Quartz counters. The popcorn ceilings were removed and re-plastered with smooth texture throughout. Both bathrooms have new vanities with Cararra marble counters, tile accent walls, including Calcatta Gold Marble Penny tile in half bath and redesigned primary bath. The bedroom features custom open concept built-in closets with soft close drawers and doors. Custom woven wood shades in living room and black out shades in bedroom. Other features include all new solid core interior doors, expansive storage closet under the stairs, owner's locker in common area, dedicated bike storage room adjacent to condo and one assigned parking space. Situated on 42 acres of manicured resort grounds and amenities, Seaplace is one of Longboat Key's most desirable communities. Enjoy two Olympic sized swimming pools, spas, one mile of trails along the shore and throughout the complex, 3 tennis courts, remodeled club house, fitness center, barbecue islands and parklike grounds. Whether you are looking for a vacation get-away, second home, investment property or permanent residence, this is the one! Seaplace is a gated community with a 24-hour guarded gate. Situated only one complex North of the famed St. Regis Luxury Hotel and Residences. This lovely condo is sold completed outfitted, fully-furnished with high quality furnishings from Pottery Barn, Restoration Hardware and comes complete with two fairly new Schwinn bicycles. Must see to appreciate. Owner has a real estate license in CA.
Listing is courtesy of: CONTINENTAL REAL ESTATE GROUP (877-996-5728)
Listing Agent: Derek Eisenberg
535 SANCTUARY DR #C807, LONGBOAT KEY, FL 34228
$3,750,000114 Days on yellowkey MLS ID: A4680240
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2580 Built: 1990 Tax: $25,298 (2025)Community: Sanctuary IvSpa: YesCondo
Taxes:$25,298
Middle School: Pine View School
Remarks: Sanctuary penthouse with spectacular views of the Gulf, and Intracoastal Waterway to Sarasota. *Now Unfurnished*. Total renovations completed in 2023 with nothing overlooked, including but not limited to EFCO turtle-approved glass, high-impact double pane hurricane sliders and windows, crystal custom kitchen cabinets by SRQ Custom Cabinetry, Thermador appliances including induction cooktop, wall-mounted microwave and convection oven, side-by-side Thermador refrigerator, Wi-Fi enabled dryer and hood fan, laundry room with added pantry features and a newly created breakfast bar. Complete water filtration system and quartz countertops throughout, with 5.5-inch baseboards with custom-milled crown molding and trim, solid wood doors, rectified 12-by-60-inch porcelain tile flooring, and custom built-ins in living room and primary bedroom. Hunter Douglas remote-controlled blinds, 10-foot-high ceilings complete with skylights, tankless hot water system, and two zoned air conditioning units installed in 2019 and 2023. Amenities include cable, water and internet. New roof in 2024. Storage locker with under-building parking. Nearly 18 acres with 1,200 feet of Gulf of Mexico beachfront, an Olympic-sized heated pool and spa with extensive pool decks, a fire pit and gazebos to provide shade. A 24/7 guard gate, Har-Tru tennis courts, on-site management, and a two-story clubhouse come complete with a fitness center, showers, saunas and a large entertaining room with catering facilities. Membership to the Longboat Key Club is available which would include six restaurants, 45 holes of golf, 20 tennis courts plus other amenities. You are close to shopping, Publix, CVS, places of worship, a library, town hall and banks, St. Armands Circle along with Sarasota and all it offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
4500 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$769,000193 Days on yellowkey MLS ID: A4671822
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,913 (2025)Community: Windward Bay AmdCondo
Taxes:$7,913
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
6700 GULF OF MEXICO DR #143, LONGBOAT KEY, FL 34228
$425,00026 Days on yellowkey MLS ID: A4692139
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 936 Built: 1969 Tax: $2,215 (2025)Community: Whitney BeachCondo
Remarks: Welcome to your coastal retreat on beautiful Longboat Key! This charming second-story condo is being offered turnkey furnished, making it completely move-in ready—just bring your suitcase and start enjoying island life. Inside, the bright living room showcases peaceful water views bringing the beauty of marine life right to your window. The kitchen features stainless steel appliances and coastal-inspired design. The home offers a relaxed, airy feel perfect for full-time living, a seasonal getaway, or an investment property. This pet-friendly and rental-friendly community is vibrant and social, offering an unmatched waterfront lifestyle. Residents enjoy private beach access, two pools, tennis and shuffleboard courts, a fitness center, and kayak launch and storage. Boating and fishing enthusiasts will appreciate the boat slips and fishing dock, while outdoor living is elevated with grill stations, picnic areas, and complimentary beach chairs. Whether you are searching for a relaxing coastal escape or an active waterfront lifestyle, this exceptional Longboat Key condo delivers the very best of Florida living with breathtaking water views, abundant amenities, and endless opportunities to enjoy the beauty of marine life and island living!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Brooke Moran (941-705-3351)
545 SANCTUARY DR #B506, LONGBOAT KEY, FL 34228
$1,828,000159 Days on yellowkey MLS ID: A4675800
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2375 Built: 1991 Tax: $19,482 (2025)Community: Sanctuary IiiCondo
Taxes:$19,482
High School: Riverview High
Remarks: Bright, spacious and beautifully maintained, this 3BR/2.5BA fifth-floor residence at The Sanctuary offers refined coastal living in one of Longboat Key’s most sought-after gated communities, ideally positioned on the island’s desirable southern end. Upon entry, walls of floor-to-ceiling glass sliders immediately draw your eye to sweeping panoramic views of the Sarasota city skyline, shimmering Sarasota Bay and the emerald fairways of the Links golf course. By night, downtown’s twinkling lights create a dramatic and ever-changing backdrop. The popular Brittany floor plan features recessed lighting, crown molding, 18-inch tile flooring throughout the main living areas and a tiled open terrace perfectly suited for sunrise coffee or evening cocktails. The kitchen has been opened to enhance flow and functionality, offering solid-surface countertops, a center island, tile backsplash and an eat-in area framed by a wall of glass. Double doors lead to the oversized primary suite, filled with natural light and offering terrace access, a walk-in closet and a spa-inspired bath with soaking tub, walk-in shower and dual vanities. Wraparound terraces further enhance the indoor-outdoor lifestyle, making this residence ideal for both everyday living and entertaining. The Sanctuary delivers an unparalleled resort-style experience with 1,200 feet of pristine white-sand beachfront, private boardwalk beach access, a heated Gulf-side pool with 25-meter lap lane, outdoor whirlpool spa and beachfront gazebo. Additional amenities include two lighted Har-Tru tennis courts, a state-of-the-art fitness center, saunas, an entertainment room, on-site management, 24-hour guard-gated security and coveted under-building parking. Pet-friendly with restrictions. Nestled behind the gates of the exclusive Longboat Key Club, this exceptional residence offers the perfect blend of luxury, privacy and breathtaking views—truly one of Longboat Key’s premier addresses.
Listing Agent: Judy Kepecz-Hays (941-587-1700)
1932 HARBOURSIDE DR #244, LONGBOAT KEY, FL 34228
$1,200,00049 Days on yellowkey MLS ID: A4689076
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1192 Built: 1982 Tax: $9,436 (2024)Community: Fairway Bay 1Condo
Taxes:$9,436
Remarks: Welcome to this breathtaking, fully remodeled, turnkey furnished contemporary residence in Fairway Bay—nestled on picturesque Longboat Key. From the moment you enter, you're greeted by a thoughtfully redesigned open floor plan, elevated ceilings, solid core doors, and impeccable high-end finishes. IT IS TRULY ONE OF A KIND! This condominium is truly one-of-a-kind! Exceptional Kitchen features include: Bertazzoni induction range, refrigerator, and dishwasher, built-in Miele plumbed espresso machine, sleek, low-profile custom cabinetry with quartz countertops, glass tile backsplash and ambient lighting and an expansive quartz island perfect for formal dining or casual entertaining. The living room flows effortlessly from the kitchen, opening onto a covered, tiled lanai—blurring the line between indoor and outdoor living. Floor-to-ceiling impact windows frame panoramic views of Sarasota Bay, the Ringling Bridge, and the city skyline, offering million-dollar scenery from the comfort of your home. Enter the generously sized and luxurious Primary Suite with custom built-ins and ample closet space. The ensuite bath is a spa-inspired bath with dual vanities, Hansgrohe Axor faucets, Toto washlet, walk-in shower with multiple heads and elegant finishes. The guest suite features custom cabinetry and an ensuite bathroom with a Victoria & Albert volcanic limestone bathtub. Other recent upgrades include Hurricane-impact windows and doors, tankless water heater, additional upper cabinetry in kitchen and utility room, ceiling fans and more. For your convenience & comfort there is easy elevator access, coveted garage parking space and private onsite storage. Fairway Bay residents enjoy the resort-Style amenities including Deeded beach access & exclusive beach club, 24-hour gated security, pool, spa, tennis courts, and fitness center plus all the perks of Bay Isles living. Whether you're soaking in the sun, enjoying vibrant Sarasota culture and nightlife, or relaxing in your private retreat, this home is a perfect sanctuary.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Jan Jordan (941-737-4169)
2425 GULF OF MEXICO DR #10F, LONGBOAT KEY, FL 34228
$1,495,000324 Days on yellowkey MLS ID: A4656887
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973 Tax: $14,482 (2024)Community: Sea Gate ClubSpa: NoCondo
Taxes:$14,482
Remarks: Price Reduced $100k—Welcome to Sea Gate Club #10F, a rare 10th-floor corner unit with sweeping, unobstructed Gulf views on Longboat Key. This 2-bed, 2-bath residence is filled with natural light and offers stunning sunsets from nearly every room—an ideal coastal retreat for relaxing or entertaining. Located in an intimate 89-unit beachfront community, Sea Gate Club offers a quiet, refined lifestyle with extensive recent upgrades, including impact windows, new roof, exterior renovation, pool, elevators, and more—no pending special assessments. Enjoy resort-style amenities: Gulf-front pool and spa, fitness center, tennis court, library, and social spaces, plus beachside extras like tiki huts and storage for bikes and water gear. Just minutes from St. Armands Circle, you’ll have easy access to dining, shopping, and island charm. Private, peaceful, and rarely available—this is Gulf-front living at its best.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Erica Thomas, Llc (941-799-9365)
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000198 Days on yellowkey MLS ID: A4671530
REDUCED by $21,000 (4.0%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $6,314 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,314
Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.
Listing Agent: Ryan Skrzypkowski (941-328-8307)
380 GULF OF MEXICO DR #515, LONGBOAT KEY, FL 34228
$1,150,00096 Days on yellowkey MLS ID: A4683391
REDUCED by $49,000 (4.1%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2380 Built: 1994 Tax: $11,342 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$11,342
Remarks: One or more photo(s) has been virtually staged. 2BD+DEN! Positioned as the southern-most community on Longboat Keys’ Gulf of Mexico Drive is the stunning Tangerine Bay. Its presence of pristinely manicured tropical color admired by all that enter the Key. Within this gated community lies #515- horizontal to Sarasota’s bayfront experiencing views that span across blue waters abundant with active sea-life. This 2bd/Den/2.5bath/2-car private garage home, with excellent wall space for displaying your finest art collection, extends over 2,300 square feet of living space. Courtyard entry, equipped with gas hook-up for your own grill, offers slider access into the kitchen/ family room area which is perfect for a different entertaining perspective since the courtyard is large enough to also accommodate table and chairs. Of course, the coveted place to dwell will be the grand living/ dining area and balcony to experience morning sun over the calming waters or the miracle of all the hues the sky can offer as the sun begins to set behind you. Large primary en-suite enjoys the water view and slider access to the balcony, considerably sized walk-in closet and super-spacious bathroom to create the spa-like atmosphere of your dreams. #515 will not disappoint with the generous kitchen, kitchen water filtration, split floorplan, updated windows and doors, 2024 remote roll-down hurricane shutters, 2023 A/C, 2026 water heater, roof and sprinkler heads replaced approx. three years ago. With a spanning lap pool, meandering lush lounging areas, spa, fishing/day dock, tennis/ pickleball, fitness center and clubhouse- Tangerine Bay is poised for pleasure to all who get to call it home. For a small annual fee, owners can also become members of the Bay Isles Beach Club.
Listing Agent: Cindy Schatzle (941-587-7556)
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,350,000230 Days on yellowkey MLS ID: A4667938
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$31,926
Remarks: The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include two under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
1975 GULF OF MEXICO DR #G4-308, LONGBOAT KEY, FL 34228
$449,000238 Days on yellowkey MLS ID: A4666939
0 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1977 Tax: $5,438 (2024)Community: Seaplace IiiSpa: YesCondo
Taxes:$5,438
Remarks: Under contract-accepting backup offers. 0.5 mi to Gulf beach access • Two heated pools & tennis courts • Gated Gulf-front community Welcome to Seaplace, a premier Gulf-front condominium community along Longboat Key’s scenic Gulf of Mexico Drive. This two-bedroom, two-bath residence (Unit G4-308) combines coastal living and community amenities in one of Sarasota County’s most desirable barrier-island locations. The open-concept layout flows seamlessly from the kitchen through the main living area to a screened lanai overlooking lush tropical landscaping and the Har-Tru tennis courts. Durable LVP flooring enhances the main living spaces, while neutral finishes allow a bright, airy feel throughout. The kitchen features ample cabinetry, and generous counter space for meal prep. The primary suite includes a walk-in closet and private bath; the secondary bedroom and full guest bath offer ideal separation for visiting friends and family. Convenient in-unit washer and dryer add everyday functionality. Residents of Seaplace enjoy approximately ½ mile of Gulf beachfront, two heated swimming pools and spas, a Gulf-side sundeck, Har-Tru tennis courts, walking paths throughout 42 acres of manicured grounds, a well-equipped fitness center, clubhouse with full kitchen and library, sauna, children’s playground, barbecue grills, and 24-hour staffed security gate. The quarterly association fee of $4,315 covers exterior maintenance, building insurance, water, sewer, cable, and amenities. Service animals are permitted per association rules; no pets otherwise. Seasonal and annual rentals are allowed with a two-month minimum. Situated along the island’s southern corridor, Seaplace offers proximity to both natural beauty and daily convenience. Publix (0.8 mi) and Bayfront Park Recreation Center (1.6 mi) provide easy access to groceries, pickleball courts, and a kayak launch. Fine dining options such as Harry’s Continental Kitchens (1.3 mi) and Euphemia Haye (1.1 mi) are nearby, along with The Shore Restaurant (1.9 mi) and the boutiques of St. Armands Circle (3.8 mi). Longboat Key Club Golf & Tennis (2.7 mi) and Downtown Sarasota (6.5 mi) offer world-class recreation and cultural attractions including the Van Wezel Performing Arts Hall, Ringling Museum, and Marie Selby Botanical Gardens. Seaplace’s Gulf-front setting provides direct beach access for sunrise or sunset walks, while community walking trails and tropical courtyards create a resort-style atmosphere year-round. This move-in-ready residence represents an exceptional opportunity to enjoy coastal living on Longboat Key, combining location, amenities, and Gulf access within a secure, well-maintained community. Includes interior laundry, screened lanai, and access to multiple pools, tennis, clubhouse, and beachfront amenities. Floor plan are available within the listing for additional detail.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228
$469,500159 Days on yellowkey MLS ID: A4675820
1 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 928 Built: 1974 Tax: $6,201 (2025)Community: Seaplace IiCondo
Taxes:$6,201
Remarks: Under contract-accepting backup offers. A perfect coastal retreat located in Seaplace, and now at an unbeleivable price! This is one of Longboat Keys most desirable beachfront communities. A light and bright 2 bedroom, 1 plus bath, 5th floor condo with a beautiful Bay view. (the photos of the view just do not do it justice!) An exceptional location in the highly sought-after Gulf-front M1 building means you can have your toes in the sand in mere moments. It is beautifully turn-key furnished and meticulously maintained and is ready for its next appreciating owner. The large primary bedroom has its own private ensuite portion of the bath with a sink that can be shut off from a full bath, making it what one would call a 1 bath PLUS. The 2nd bedroom offers a perfect spot for visitors to help you enjoy this amazing way of life to the fullest. Seaplace offers resort style living with unmatched amenities that include 2 large pools and hot tubs; a kiddie pool; 3 har-tru tennis courts; a recently renovated Gulf-front clubhouse; a fitness center; library; gas grills; a one-mile paved walking path surrounding the lush 42-acre property, and a gatehouse with 24-hour security. Located near the newly opened St.Regis Resort, St.Armands Circle and the cultural epicenter of downtown Sarasota, you’ll be close to world-class restaurants, hotels, entertainment, arts, culture, and shopping. Come see this fabulous condo soon and make your island living dream a reality in 2026!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228
$530,000142 Days on yellowkey MLS ID: A4676925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,041 (2024)Community: Longboat HarbourCondo
Taxes:$6,041
Remarks: Located in the gated waterfront community of Longboat Harbour, this updated first floor residence offers direct walkout access to manicured green space and peaceful water views. Positioned near deeded beach access, the home provides a seamless blend of coastal living and everyday convenience. Interior features include tile flooring throughout, Frigidaire appliances, plantation shutters and automated blinds. The residence is offered turnkey furnished, including a West Elm leather sofa, coordinated coastal accent tables, coffee table, breakfast set and dining table with six chairs. The air conditioning system was replaced approximately two and a half years ago. All appliances and the hot water heater are under warranty, including parts and labor, through February 2027. Covered assigned parking and ample guest parking are included. Longboat Harbour is home to the Longboat Yacht Club, offering an active social calendar and waterfront gatherings for residents, whether or not they maintain a slip. Dock slips are available on a first-come basis for $460 per year. Community amenities include kayak storage and launch, seasonal dock rentals, a fitness center with instructor-led classes, tennis and pickleball courts, sauna, craft room, woodshop, library, and game rooms. No pets permitted. Rentals allowed twice annually with a 30 day minimum.
Listing Agent: Sharon Meier (407-927-5669)
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000328 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,600,00078 Days on yellowkey MLS ID: A4685503
REDUCED by $150,000 (2.2%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Taxes:$50,055
High School: Sarasota High
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
1930 HARBOURSIDE DR #145, LONGBOAT KEY, FL 34228
$549,00051 Days on yellowkey MLS ID: A4686987
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $50,000 (8.3%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982 Tax: $8,215 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$8,215
Remarks: Under contract-accepting backup offers. Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where shifting blue and green tones take center stage. The layout flows effortlessly from the updated kitchen into the dining area and living room, allowing the view to remain the focal point throughout. The kitchen has been thoughtfully redesigned with striking stone countertops, low-profile white cabinetry, a refined tile backsplash and stainless-steel appliances. The living room opens to an expansive terrace through a full wall of sliders, offering a front-row perspective of the mangroves and channel, where boats pass by and manatees are often seen gliding through the water—creating a setting that feels both peaceful and connected. The primary suite serves as a private retreat with rich wood flooring, direct terrace access and a well-appointed bath featuring dual vanities and a separate water closet. The guest bedroom is comfortably sized, and the guest bath has also been tastefully updated. Residents of Fairway Bay enjoy a bayside lifestyle with deeded beach access through the private Bay Isles Beach Club, one underbuilding parking space, 24-hour gated security, walking trails, a heated pool, tennis courts and a fitness center. Membership opportunities at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available, and small pets up to 15 pounds are welcome.
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