Location: Longboat Key
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5055 GULF OF MEXICO DR #421, LONGBOAT KEY, FL 34228
$549,00072 Days on yellowkey MLS ID: A4684543
REDUCED by $26,000 (4.5%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,224 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,224
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Set within the highly regarded Club Longboat Beach & Tennis on Longboat Key, this 2BR/2BA residence offers an excellent opportunity to create something truly special in one of the island’s most amenity-rich communities. Just under 1,500 sq. ft. and located on the second level, the residence enjoys a comfortable layout where the primary suite opens to a private terrace, bringing in light and breezes throughout the day. The dining area features a tray ceiling and flows easily into the living room, where a full wall of sliders leads to an open terrace and invites indoor and outdoor living to blend naturally. The space is ready for your personal design vision, offering a solid canvas in a location where lifestyle often takes center stage. Life at Club Longboat Beach & Tennis is known for its mix of recreation, flexibility and beachfront access. Residents enjoy 750 feet of pristine shoreline, eight Har-Tru tennis courts, pickleball courts, two heated pools, a fitness center and a relaxed, social atmosphere. Pet-friendly with 2 pets, no weight restrictions and a rental policy allowing one-month minimum stays up to twelve times per year, this residence is ideal for a full-time escape, seasonal retreat or investment opportunity.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
4825 GULF OF MEXICO DR #105, LONGBOAT KEY, FL 34228
$799,000238 Days on yellowkey MLS ID: A4667044
REDUCED by $40,900 (4.9%) on 05/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1393 Built: 1970 Tax: $11,897 (2024)Community: Westchester AptsSpa: NoCondo
Taxes:$11,897
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$599,000121 Days on yellowkey MLS ID: TB8455704
REDUCED by $26,000 (4.2%) on 05/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970Monthly Fee: $1,412 Tax: $3,678 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$3,678
Tax Year: 2025
Remarks: Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
1935 GULF OF MEXICO DR #G7-304, LONGBOAT KEY, FL 34228
$465,00047 Days on yellowkey MLS ID: TB8496217
0 Days Off yellowkey (back on 5/19/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 933 Built: 1979Monthly Fee: $1,367 Tax: $4,940 (2025)Community: Seaplace ViCondo
Taxes:$4,940
Remarks: Under contract-accepting backup offers. Experience the best of coastal living in this beautifully maintained 2-bedroom, 1-bathroom condominium, perfectly situated on the third floor of the desirable Seaside community on Longboat Key. Set within a secure, 24-hour guard-gated enclave, this charming residence offers both privacy and peace of mind. Step inside to discover a light and airy interior that was tastefully repainted in April 2021, along with stylish updates to the kitchen and bathroom completed at the same time. The functional layout includes a spacious living area that opens to a generously sized screened-in patio—an ideal space for enjoying morning coffee, evening breezes, or simply soaking in the serene surroundings. A brand-new air conditioning system was installed in October 2024, ensuring year-round comfort and energy efficiency. The building’s exterior also received a fresh coat of paint in April 2021, enhancing its curb appeal and overall charm. This coastal retreat offers direct access to the soft sands and crystal-clear waters of the Gulf, making beach days effortless and spontaneous. Residents also enjoy an array of resort-style amenities, including two heated swimming pools with relaxing spas, a well-equipped fitness center, a playground, three tennis courts, a welcoming clubhouse, and tranquil walking trails that wind through the community. Located just a short drive from the boutique shops, fine dining, and vibrant atmosphere of St. Armands Circle, this property is ideal for full-time residents, seasonal getaways, or investment opportunities. Leasing is allowed with a twomonth minimum lease period, up to six times per year, offering flexibility for owners. Don’t miss your chance to own a piece of paradise on Longboat Key!
Listing is courtesy of: EATON REALTY (813-672-8022)
Listing Agent: Alie Espinoza (813-382-6465)
1145 GULF OF MEXICO DR #401, LONGBOAT KEY, FL 34228
$1,250,000131 Days on yellowkey MLS ID: A4678330
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1172 Built: 1980 Tax: $13,294 (2025)Community: Beachplace ICondo
Taxes:$13,294
Remarks: Under contract-accepting backup offers. This highly desirable 4th floor corner residence at Beachplace boasts full direct views of the Gulf from almost every room. Renovated in a coastal contemporary style with long plank porcelain tile flooring throughout, the island lifestyle is readily apparent upon entering. The kitchen offers azure water views while meal prepping, stainless steel appliances, breakfast bar, granite counters and a closet pantry. The primary bedroom pampers owners with access to the covered terrace, spacious primary bathroom offering dual vanities and expansive water views. Highlights include impact windows, TWO Parking Spaces, new entry door, updated flooring in the bedrooms and new interior doors. With an excellent rental policy of 1 month minimum/12 times a year, there is healthy income potential - call for more details. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, fitness center, clubhouse, on-site management and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota. Your Longboat Life awaits! RENTALS IN PLACE CONVEY WITH SALE.
Listing Agent: Ian Addy, Pa (941-961-8850)
2110 HARBOURSIDE DR #536, LONGBOAT KEY, FL 34228
$749,00037 Days on yellowkey MLS ID: A4685244
REDUCED by $50,000 (6.3%) on 05/12/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988 Tax: $12,286 (2025)Community: Fairway Bay 3Spa: YesCondo
Taxes:$12,286
Remarks: Under contract-accepting backup offers. Completely reimagined with an uncompromising eye for detail, this furnished, southeast-facing 3-bedroom residence in The Atrium of Fairway Bay offers refined living with sweeping views across the lagoon, mangroves, open bay, and Sarasota skyline beyond. Thoughtfully remodeled with no expense spared, the flexible layout feels both elegant and exceptionally functional. Rich wood floors run throughout the main living areas, grounding the residence in warmth and sophistication while complementing the shimmering water and city views beyond the glass. A curated mix of tile, wood, stone, and carefully selected colors creates a distinctive ambiance throughout. In the living room, a full wall of sliders opens to a covered terrace that invites the outdoors in and captures the tranquil beauty of the surrounding vistas. Recessed lighting, 8-inch crown molding, plantation shutters, custom-built cabinetry, and a dry bar with wine fridge elevate the space with both style and purpose. The kitchen is beautifully tailored for daily living and entertaining alike, featuring a large custom island with cooktop, granite counters, tile backsplash, tray ceiling, Bosch stainless steel appliances, a built-in desk, and an oversized custom pantry that adds rare storage and convenience. The primary suite is a spacious retreat, highlighted by a dramatic corner wall of floor-to-ceiling glass and slider access to the terrace. Its bath is generously sized and beautifully finished with dual vanities, warm wood accents, and a glass walk-in shower with built-in bench. Two additional bedrooms provide flexibility for guests, a home office, or den, complemented by a beautifully updated full bath. Additional features include an in-residence laundry room and a top-tier AC system equipped with ultraviolet germicidal UV light and an Ecobee smart programmable thermostat. Located behind the gates of Bay Isles, The Atrium of Fairway Bay offers a relaxed, amenity-rich lifestyle with two community pools, tennis courts, fitness facilities, beautifully landscaped bayfront walking paths, kayak access, and deeded Gulf beach access through the Bay Isles Beach Club. Residents also enjoy 24-hour gated security, with optional access to Longboat Key Golf & Tennis Country Club memberships and deepwater slips.
615 DREAM ISLAND PL #210, LONGBOAT KEY, FL 34228
$949,90026 Days on yellowkey MLS ID: TB8503989
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1509 Built: 1985 Tax: $11,560 (2024)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$11,560
Remarks: Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year round, or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay. Bright and spacious, the open floor plan features soaring 9 ft ceilings, custom finishes, a gourmet kitchen with top-of-the-line appliances and a sleek wet bar. The primary suite offers stunning water views, dual closets, and a spa-inspired bath. The second bedroom is spacious and set apart from the primary. Step into the enclosed lanai for breathtaking 180° water views and added living space— perfect for relaxing or entertaining. This unit comes with a deeded 40' boat slip #3 which features upgraded power and plumbing, new wraps, caps, marine grade bumpers and a deck box- a rare bonus that can accommodate a 55' vessel! Harbour Villa Club is nestled in a quiet corner and you can walk or bike to the beach, area restaurants, and beloved Harry's Corner Store. This is a pet friendly community with covered parking, storage, elevators, kayak and bike storage, private dock, heated pool, tennis/pickleball courts, grills and beautiful landscaping. Weekly rentals allowed. Call today!
Listing is courtesy of: CENTURY 21 BILL NYE REALTY (813-782-5506)
Listing Agent: Lori Lahart (813-297-9610)
3427 WINDING OAKS DR #14, LONGBOAT KEY, FL 34228
$1,150,00065 Days on yellowkey MLS ID: A4686623
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2555 Built: 1988 Tax: $13,850 (2025)Community: Winding OaksSpa: NoCondo
Taxes:$13,850
Elementary School: Southside Elementary
Remarks: Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota’s coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership—ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances—perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area—while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.
Listing Agent: Carolyn Donnelly, Pa (941-350-9900)
4325 GULF OF MEXICO DR #103, LONGBOAT KEY, FL 34228
$1,100,00012 Days on yellowkey MLS ID: A4693621
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1336 Built: 1975 Tax: $4,084 (2025)Community: Tiffany PlazaSpa: NoCondo
Taxes:$4,084
Remarks: Experience coastal living in this two-bedroom, two-bath direct Gulf-front residence ideally on the main floor of a desirable mid-rise community on Longboat Key. Freshly painted and thoughtfully enhanced with quartz countertops in both the kitchen and laundry room, along with recently updated washer and dryer appliances, the residence also features crown molding, updated trim and plantation shutters throughout, as well as Gulf-side hurricane shutters. The covered Gulf-side lanai provides the perfect setting to relax and enjoy the coastal surroundings year-round. The primary bedroom offers a very large walk-in closet. This residence includes a designated covered parking space along with private exterior storage. Residents enjoy an impressive array of amenities, including a clubhouse with a sauna, a heated Gulf-front pool, an interlocking stone patio and barbecue, a covered area and direct beach access. Ideally in a sought-after mid-key location, the property is close to St. Armands Circle, with its renowned boutiques, dining and shopping, while downtown Sarasota is just over the bridge, offering arts, culture, dining and entertainment. Heading north, enjoy convenient access to Anna Maria Island, while heading south, you will find the many amenities of Longboat Key, including Publix, CVS, places of worship, banks, parks, town hall, Bayfront Park, public tennis courts, boat launches and more.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$675,00057 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Taxes:$5,662
Middle School: Booker Middle
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
815 BAYPORT WAY #815, LONGBOAT KEY, FL 34228
$850,00049 Days on yellowkey MLS ID: A4689278
0 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1601 Built: 1981 Tax: $7,370 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$7,370
High School: Booker High
Remarks: Under contract-accepting backup offers. Welcome to a true hidden gem of tropical paradise at Bayport Beach and Tennis Club on Longboat Key. Designed by renowned architect Tim Seibert, this one-of-a-kind community spans 27 lush, tropical acres and offers an unmatched coastal lifestyle with 1,200 feet of pristine private beach, where chairs and umbrellas are ready for you to enjoy endless days along the Gulf. As you arrive, you’re immediately surrounded by beautifully maintained grounds and the relaxed, resort-style atmosphere that makes this community so special. Stepping inside this spacious 2 bedroom, 2 bathroom furnished residence, you’re welcomed by a light and airy interior with terracotta-look tile flooring flowing throughout the main living areas, setting a warm coastal tone. The kitchen has been thoughtfully renovated with all new cabinetry, under-cabinet lighting, quartz countertops, a modern backsplash, and stainless steel appliances, creating a clean and functional space that opens seamlessly into the living and dining areas. The expansive living room is both inviting and impressive, designed to feel like a single-family home, with stunning Sarasota Bay views that instantly capture your attention. Shutter doors provide privacy while leading into a sunroom, offering a flexible space to relax and take in the scenery. The owner’s suite is a true retreat, complete with a dedicated office nook perfectly positioned to enjoy peaceful water views. The ensuite bathroom features dual quartz-topped vanities and a walk-in closet, combining comfort and convenience. A split bedroom floorplan ensures privacy, with the guest bedroom offering its own walk-in closet and easy access to the updated guest bathroom. An in-unit laundry area adds to the everyday ease of living. Step outside onto your expansive private deck, where breathtaking views of Sarasota Bay create the perfect backdrop for morning coffee, evening wine, or entertaining guests while surrounded by nature. Bayport Beach and Tennis Club offers an incredible array of amenities, including a Junior-Olympic heated pool, four Har-Tru tennis courts, a fitness center, fishing pier, kayak storage + launch, and an active clubhouse filled with social events. Scenic walking trails wind through the property, where you’ll often spot local wildlife such as osprey, herons, ibis, and egrets, enhancing the serene, natural setting. Just moments away, Bayfront Park offers pickleball courts, green space, and stunning bay views, while St. Armands Circle provides exceptional shopping and dining. A short drive over the iconic Ringling Bridge brings you into vibrant downtown Sarasota, known for its world-class arts scene, including theaters, museums, galleries, and waterfront dining. From private beach access to unmatched amenities and breathtaking bay views, this residence offers the perfect blend of comfort, nature, and coastal elegance in one of Longboat Key’s most sought-after communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Keith Curcio (941-376-7683)
836 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$995,000166 Days on yellowkey MLS ID: A4674750
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2813 Built: 1991Monthly Fee: $1,644 Tax: $4,852 (2025)Community: Cedars East Sec 3Condo
Taxes:$4,852
Remarks: Bay Views! Investor Dream Home! A double condo unit which feels like a single-family home, because it is not attached to anything but sunshine, the bay and dreams! Elevated among the treetops on the bay side of Longboat Key, it features 2 oversized garage spaces, wood floors throughout the first elevated living level, an open great room with a large open kitchen for entertaining, an inviting wood-burning fireplace, screened lanai for bay breezes and a office/den/flex room. Upstairs you will find 2 guest bedrooms which share a full bath and a primary bedroom with a view of Sarasota Bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. The ensuite primary bath features dual sinks and 2 large walk-in closets. Amenities in the premier tennis community include exceptional access to Bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!
Listing Agent: Eileen Saunders (662-404-0816)
1145 GULF OF MEXICO DR #503, LONGBOAT KEY, FL 34228
$1,395,00092 Days on yellowkey MLS ID: A4683782
3 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1503 Built: 1980 Tax: $13,436 (2025)Community: Beachplace ISpa: YesCondo
Taxes:$13,436
Remarks: Welcome to Beachplace #1-503, a coveted fifth-floor direct Gulf-front getaway in Building 1, offering panoramic beach and Gulf views from one of Longboat Key’s most desirable waterfront communities. Encompassing 1,503 square feet of interior living space, this two-bedroom, two-bath residence delivers front-row access to turquoise waters and spectacular sunset skies. Extensively updated, this residence features oversized diagonal tile flooring throughout, enhancing flow and visual continuity. Impact windows, sliders, and doors were installed in 2017, providing added peace of mind. The open-concept kitchen was thoughtfully redesigned to maximize Gulf views, showcasing rich solid-wood cabinetry in a mahogany finish, granite countertops, tile backsplash, breakfast bar, and stainless-steel appliances. This modernized culinary space connects effortlessly to the dining area and great room, ideal for entertaining while overlooking the beach. The primary suite occupies the northwest corner to capture sweeping water views and evening sunsets. French door access to the terrace and an updated en-suite bath with quartz surfaces, dual sinks, and a glass-enclosed shower create a private retreat. The guest bedroom is positioned on the east side of the residence, also en-suite, offering comfort and privacy for visitors. Positioned beneath the penthouse extended terrace above, the covered Gulf-front balcony provides shaded outdoor living—an ideal vantage point for year-round enjoyment of the shoreline. Walls of impact-rated glass sliders open from the living room directly to the terrace, creating a seamless connection to the water and filling the interior with natural light. Beachplace is a gated Gulf-front community with 24-hour guard security, on-site management, and resort-style amenities. Residents enjoy a heated beachfront swimming pool and spa, clubhouse, fitness center, Har-Tru tennis courts, pickleball, and a private boardwalk to access the beach. Assigned parking and elevator access add convenience to this elevated mid-rise building. Located on the southern end of Longboat Key, Beachplace offers immediate access to the Longboat Key Club’s golf and tennis facilities (requires separate membership), nearby marinas, and the boutiques and restaurants of St. Armands Circle. Downtown Sarasota is just minutes away, where theaters, galleries, waterfront parks, and renowned dining complete the lifestyle. Whether enjoying a morning walk along the Gulf or an evening performance downtown, this direct beachfront residence places the very best of Sarasota living within easy reach.
Listing Agent: Roger Pettingell (941-387-1840)
2410 HARBOURSIDE DR #131, LONGBOAT KEY, FL 34228
$1,849,00012 Days on yellowkey MLS ID: A4693248
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 3825 Built: 1993 Tax: $15,203 (2025)Community: Marina BaySpa: YesCondo
Taxes:$15,203
Remarks: Dramatic Sarasota Bay views and a true “house-size” floor plan define this spacious 3BR/3.5BA residence in Marina Bay with 3,825 sq. ft. of living space. A private elevator lobby opens directly into the home, where generous living and dining areas, a formal foyer, powder room, separate family room, and two terraces create an easy flow for everyday living and entertaining. All three bedrooms feature en-suite baths and terrace access, while the primary suite enjoys panoramic bay and skyline views, separate bath areas, a large shared shower, jetted tub, and excellent closet space. The kitchen includes Sub-Zero refrigeration, solid-surface counters, breakfast area, and ample storage. A separate den with custom built-ins, bar area, and wine storage adds a comfortable office, media, or flex space. Marina Bay is a gated waterfront community in Bay Isles offering secured under-building parking, pool, spa, fitness center, tennis, pickle ball, storage, waterfront amenities, and beautifully maintained grounds. Residents also enjoy deeded access to the private Bay Isles Beach Club on the Gulf, with beach facilities, picnic areas, grills, and a relaxed residents-only setting. Optional membership to the Longboat Key Club is available separately, offering golf, tennis, dining, beach and pool amenities, spa, fitness, wellness programming, club events, and nearby marina access. Conveniently located close to Publix, CVS, restaurants, Longboat Key Club, St. Armands Circle, and downtown Sarasota.
3060 GRAND BAY BLVD #174, LONGBOAT KEY, FL 34228
$1,798,000142 Days on yellowkey MLS ID: R4910478
REDUCED by $141,000 (7.3%) on 05/17/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1994Monthly Fee: $2,617 Tax: $17,500 (2024)Community: Grand Bay 1Spa: YesCondo
Taxes:$17,500
Remarks: PRICE POINT ADJUSTMENT ON HIGH FLOOR UNIT! Resort Living At It's Finest with this Grand Bay Condominium offers Privacy in the exclusive Bay Isles community. Grand Bay is situated directly on Bishops Point offering extensive Sarasota City views. Get swepted away by the dramatic unobstructed views of the city and expansive Sarasota Bay. The expansive floor to ceiling"Walls of Windows" with terraces on both the east and west sides of the building. Perfect sunrises and sunsets are the order the day ! The open floor plan from living room, to dining room, to den (can be easily converted into a 3rd bedroom) and the convenience of the kitchen all flow smoothly for entertaining and easy living. The den, kitchen, and guest bedroom all face west with access to the terrace for spectacular sunsets. The kitchen offers all of the latest modern conveniences with an oversized SubZero refrigerator/freezer, mini Perlick bottle refrigerator, Bosch dishwasher, Wolf triple oven with microwave, warming oven and Empava induction cooktop. This unit is sold fully furnished with high end quality names like Ethan Allen, Hancock & Moore and Italian leather. The master bedroom boasts panoramic views of the city and connects to the east terrace with plenty of space for sunbathing and nature watching. The marble master bath invites you to soak in the garden tub to relax the day away. Grand Bay Building 1 Caymen unit offers Total Privacy on the East and West Balconies with Glass railings for unobstructed viewing privacy! The en-suite guest bedroom is currently being used as an office and features its own grand views of the Longboat Key’s Harbourside golf course and the Gulf of Mexico beyond. Grand Bay is situated behind the Longboat Key Club gates and offers additional gated security at the building entrance for your peace of mind. Amenities for your enjoyment include two Har-Tru tennis courts, a state-of-the-art fitness center on the second floor of the Newly modernized Grand Bay clubhouse, two large heated pools and private beach access to the Newly modernized PRIVATE Bay Isles Beach Club directly on the Gulf of America. Grand Bay offers Electric Car Charging Stations. The Travertine stone floors are polished to perfection and is in pristine condition. This is resort style living, at its finest with the convenience of being located on Longboat key. Just minutes from St. Armand's world renowned shopping, restaurants and the cultural capital of Florida that is downtown Sarasota. Memories that will last a lifetime....All offers submitted via FAR-BAR contract form. Please use showing time button for all showings
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
775 LONGBOAT CLUB RD #807, LONGBOAT KEY, FL 34228
$2,295,000229 Days on yellowkey MLS ID: A4667077
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1842 Built: 1984 Tax: $10,487 (2024)Community: Beaches Of Longboat Key Ph-1Condo
Taxes:$10,487
Middle School: Pine View School
Remarks: Welcome to Beaches of Longboat Key - Unit 807 From a morning stroll on the beach to twilight cocktails on your wrap around balcony watching the glittering lights of Sarasota over the bay, you will experience beauty all around. Longboat Key, a jewel in the crown of the Sarasota Coastline, has so much to share. This elegantly appointed home will not disappoint. Custom finishes are abundant throughout the 1,842 sq ft condominium, not to mention the breath-taking views from the over 300 sq ft wrap-around balcony. This gracious home offers generous living space, with sweeping views from every window. Upon entering 807, you are greeted to stunning engineered Brazilian Cherry Hardwood flooring that continues throughout the home. A Reme Halo Air Purification System keeps the air fresh and clean. All windows and sliders are Impact. Beautiful crown molding throughout. The custom kitchen created by Campbell’s Cabinetry, Quartzite countertops, SubZero 42” Side by Side Refrigerator Freezer, Wolf Steam Convection Oven, GE Monogram Induction Cooktop, Zephyr PISA range hood. Bosch Dishwasher, Blanco Silgranite Sink, Hansgrohe Faucet. Custom cabinetry can be found throughout this beautiful residence. Primary Bedroom Suite offers views, comfort and luxury. Two bedrooms, each with well-designed baths, custom touches are found everywhere. There is one assigned parking space assigned to the unit on the upper level, and there is ample parking on the lower level for your second vehicle. Beaches is a great community offering you every convenience: 24-hour Concierge, Heated pool & Spa, Fitness Room, Tennis Courts, Social Room, Catering Kitchen, direct Walkway access to the Beach and a Basement Storage area. This proactive community is hard at work completing several important and vital projects: Stack Pipelining throughout the building, Roof Replacement will take place later this year and Temporary Wind/Surge Barriers are being purchased to protect the main floor of the building. Morning, noon and night, there is always something wonderful to experience at Beaches on beautiful Longboat Key. Schedule you showing today!
Listing Agent: David Stasney (941-705-8464)
4234 GULF OF MEXICO DR #D1, LONGBOAT KEY, FL 34228
$595,000177 Days on yellowkey MLS ID: A4673543
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1248 Built: 1973 Tax: $2,929 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$2,929
Remarks: Waterfront Gem. Refined coastal renovation, waterfront location, deeded beach, pet-friendly, pickleball, tennis, kayaking, boating, and the best of casual island living. Enjoy the larger D1 floorplan, offering owners more square footage in this open concept two-bedroom, two-bath condominium in Longboat Key's Pelican Harbour & Beach Club. Plus this unit comes totally turnkey furnished and is move-in ready. The Association's amenities include private beach, tennis and pickleball courts, heated resort-style pool, clubhouse, bike storage, kayak launch, and owner boat docks. The condominium features include hurricane windows and doors, contemporary-style fireplace, new flooring, custom cabinetry, stainless appliances, crown molding, plantation shutters, tankless water heater, new air conditioner, and designer ceiling fans. Spacious primary suite boasts a private bath with custom walk-in shower, built-in closets, and water views. The guest suite, split from the primary, offers friends and family alike private space and a convenient adjoining bath with a custom walk-in shower, as well. There is plenty of closet space and storage throughout, and an in-unit laundry with matching front-load HE washer and dryer. In addition, with the D1 plan being larger than other Pelican Harbour two-bedroom condominiums, owners will appreciate the larger spaces for gathering and hosting. Association provides on-site maintenance; landscaping; building property, wind, flood and liability insurances; roofs; exterior painting; cable; water; sewer; trash; and more. Pelican Harbour also has fully funded reserves and has installed new roofs, new hurricane-rated carports, upgraded pickleball and tennis courts, and offers owner boat docks with electric and water. Pelican's private beach is only steps away and offers stunning sunset and Gulf views with miles of turquoise waters and crystal sands. You'll also appreciate the convenient mid-island location close to Bayfront Park, grocery, restaurants, shopping, places of worship, and easy access to St. Armands, Sarasota and Anna Maria. Gorgeous coastal renovation, larger D1 floor plan, fantastic mid-island location, pet-friendly and one of the best amenity packages on the island. Enjoy Pelican Harbour and Beach Club. Schedule your private showing.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,00061 Days on yellowkey MLS ID: A4687586
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1148 Built: 1973 Tax: $6,756 (2025)Community: Sutton PlaceCondo
Taxes:$6,756
Remarks: This is the one you have been waiting for!! INCREDIBLE UNOBSTRUCTED BAY VIEWS & BREATHTAKING SUNRISES from this light-filled CORNER unit in the beach-to-bay community of Sutton Place. Enjoy stunning vistas from nearly every room through impact windows and doors! Meticulously maintained and beautifully renovated, this spacious two-bedroom, two-bath coastal retreat is truly exceptional. The thoughtfully designed open concept chef’s kitchen with premium cabinetry, plentiful storage, and Cambria quartz countertops seamlessly connects to the expansive living area through a custom dining island with wraparound seating. Plantation shutters throughout the kitchen and living area add to the coastal island feel. The enclosed lanai, featuring walls of glass that span along the rear of the unit, provides an ideal setting for morning coffee, evening relaxation, remote work, or accommodating additional guests. The spacious primary and secondary bedrooms provide exceptional views, each with direct access to the lanai through impact-rated sliding doors. The serene primary bedroom boasts a generous walk-in closet fitted with a custom organizer and an elegantly renovated bathroom with a walk-in shower, complete with a linen closet. The secondary bedroom offers ample storage with a double closet, also fitted with custom organizers. The adjacent guest bath has been tastefully renovated. Parking is easy with a covered, assigned space in a convenient location, plus plenty of overflow and guest parking. While the stairs are easily accessible; there is also an elevator for added convenience. The in-building storage unit provides extra space for any additional storage needs. Sutton Place offers a wide range of amenities, including two heated swimming pools, a community clubhouse, marina facilities with boat slips (current wait list but only $300 annually!!), kayak storage equipped with electric launch, a fish cleaning station, designated grilling areas, car wash stations, and deeded beach access with private beach pavilion featuring storage lockers, showers, and restrooms. The community successfully endured the recent storms, experiencing minimal overall damage and no impact to any individual units. With its exceptional location, unmatched views, and wonderful amenities, this property is an opportunity not to be missed! Schedule your private showing today!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Melissa Rodocker (703-969-2345)
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00047 Days on yellowkey MLS ID: A4687549
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,164 Tax: $3,185 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,185
Remarks: Experience the best of Gulf-front living and gorgeous views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is walking distance to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a locking owner's closet in the unit. You have to see this home to really appreciate how special it is.
Listing Agent: Judy Mitchell (941-275-6838)
4485 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$1,075,00037 Days on yellowkey MLS ID: A4690646
REDUCED by $20,000 (1.8%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1175 Built: 1973 Tax: $6,115 (2025)Community: Arbomar AptsCondo
Taxes:$6,115
Remarks: Direct Gulf-front 2BR/2BA on the 8th floor of Longboat Key's Arbomar. Panoramic sunset views, renovated interior, pets allowed, low HOA fees. Direct Gulf-front condo with unobstructed views rarely available on Longboat Key! This 8th-floor residence at The Arbomar delivers panoramic views of the Gulf of Mexico, white sand beaches and sunsets that fill the horizon year-round. This 2-bedroom, 2-bath home offers 1,175 sq. feet and the kind of setting buyers often wait years to find. Inside the renovated kitchen features wood cabinetry, quartz countertops, under-cabinet lighting, and stainless-steel appliances. Ceramic tile flooring runs through the main living areas, while crown molding plantation shutters and custom built-ins add clean, timeless detail throughout. Electric hurricane shutters ensure peace of mind and long-term value. Wake to open water views and end the day with the changing colors of the sunset from your private 8th-floor vantage point. Whether used as a full-time residence or seasonal retreat, this home offers the everyday ease that draws buyers to beachfront living in the first place. Most recent improvements include fully renovated kitchen, updated bathrooms, a newer HVAC system, and a tankless water heater. The Arbomar also completed major exterior upgrades including new roof, hurricane-rated insulated windows, new entry and storm doors, and water-resistant Gemstone concrete coating on lanais and common area breezeways. Community amenities include a Gulf-front heated pool, fitness room, club room, community kitchen, kayak storage, and climate-controlled storage lockers. The condominium association is well-managed and well-funded, with low quarterly fees of $4,000. Ownership details include one-month minimum rentals permitted up to four times per year after the required ownership holding period. Pets are permitted for owners, while rentals are pet-free. The residence conveys unfurnished and includes one assigned carport space with additional guest parking available. Located on Gulf of Mexico Drive, this Longboat Key address places you near island dining, golf, boating, shopping, St. Armands Circle, and downtown Sarasota. For buyers seeking a true beachfront position, updated condition, and views that never get old, this residence stands apart.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-260-3350)
Listing Agent: Julie Larson, Llc (941-284-9826)
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