Location: Longboat Key
Do Not Show Listings
3540 GULF OF MEXICO DR #102, LONGBOAT KEY, FL 34228
$599,00029 Days on yellowkey MLS ID: A4685789
1 Days Off yellowkey (back on 4/2/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1284 Built: 1980 Tax: $5,007 (2025)Community: Buttonwood CoveCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,007
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: This perfect slice of paradise offers Spectacular Bay Views for Beautiful Sunrises from your Spacious Lanai or Primary Bedroom and Deeded Beach Access for Breath Taking Sunsets. To top it off you have an assigned, deep water slip for your boating needs with no bridges to the intercoastal. This beautiful 2 bedroom, 2 bath, 1,284 sqft Condo is a first floor unit, above the garage level. Split Floor Plan delivers separation from your Primary Bedroom Suite and your Guestroom. Bright white walls and updated ceilings with recessed lights add to the bright airy feel. Open concept Living Room and Dining Room combination. Plantation shutters, impact windows. Tastefully decorated and furnished with exclusions. Complex offers park like grounds, a beautiful Heated Pool and Tennis/Pickleball courts for when you are done boating or enjoying the views. Assigned Garage Level Storage Closet and Parking Space. Convenient mid key location, less than a mile from Publix and CVS, and a short ride to the shops and restaurants of St Armand’s and Downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Sean Clark (941-312-1146)
3030 GRAND BAY BLVD #323, LONGBOAT KEY, FL 34228
$1,250,00070 Days on yellowkey MLS ID: A4681067
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1998 Tax: $9,798 (2025)Community: Grand Bay 3Condo
Taxes:$9,798
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: This sought-after 2,550 sq. ft. Cayman model in Grand Bay is located within the community’s desirable Building III and ideally positioned to capture magnificent Sarasota Bay and sparkling city views, with additional vistas overlooking the Harbourside Golf Course. Approximately 700 square feet of outdoor living includes two expansive terraces: an east-facing for breathtaking sunrises over the bay and a west-facing showcasing unforgettable glowing sunsets. A private elevator foyer opens to the spacious living area with 9-foot ceilings and immediate “wow” views of the bay. The primary suite is thoughtfully positioned for privacy, featuring serene bay views, a sliding glass door to the bayfront terrace, and an updated primary bathroom with dual bath areas. The guest bedroom is located on the west side of the residence with direct access to the west-facing terrace. The den, considered an occasional 3rd bedroom, offers exceptional flexibility with two sets of concealed movable doors allowing this space to be closed off from the kitchen and dining areas for privacy, and it enjoys access to a third full bath. The dining room is centrally located, enhancing the open flow between living spaces while offering both bay and west-exposure views. The kitchen includes a breakfast room and abundant cabinetry. Luxury vinyl flooring runs throughout the residence. The condominium is being sold partially furnished for the new owner to begin their coastal journey with ease. Grand Bay residents enjoy an exceptional array of resort-style amenities, including two heated pools & spas, two Har-Tru tennis courts, a state-of-the-art fitness center with sauna, 24-hour guard-gated security, and on-site management. Miles of sidewalks and trails wind throughout the natural beauty of Bay Isles, a true sanctuary for nature lovers. Bay Isles Beach Club membership is included exclusively for owners, offering gated parking and private beach access with beach amenities, grills, and conveniences. Optional Longboat Key Club membership, including golf, is also available.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
380 GULF OF MEXICO DR #515, LONGBOAT KEY, FL 34228
$1,199,00053 Days on yellowkey MLS ID: A4683391
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2380 Built: 1994 Tax: $11,342 (2025)Community: Tangerine Bay ClubCondo
Taxes:$11,342
Remarks: One or more photo(s) has been virtually staged. 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 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 is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
603 LONGBOAT CLUB RD #402N, LONGBOAT KEY, FL 34228
$1,250,000161 Days on yellowkey MLS ID: A4670556
1 Days Off yellowkey (back on 4/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1458 Built: 1970 Tax: $13,618 (2025)Community: Longboat Key TowersCondo
Taxes:$13,618
Remarks: Under contract-accepting backup offers. Nestled behind the exclusive gates of the Longboat Key Club, Longboat Key Towers stands as one of the island’s most distinguished Gulf-front communities. Within the north tower, this elegant fourth-floor residence captures breathtaking views from sunrise to sunset — with two expansive balconies overlooking the shimmering Gulf of Mexico to the west and the rolling greens and bay waters to the east. The living and dining areas frame the Gulf like a work of art, with floor-to-ceiling picture windows that make you feel as though you’re floating above the shoreline. A thoughtfully designed kitchen offers generous cabinetry, pantry storage, a full suite of appliances, and a convenient service entrance. A gracious double-door entry opens to a welcoming foyer that leads to the guest quarters and bath. The spacious primary suite features a walk-in closet, a separate vanity area, and a private bath, with both bedrooms sharing access to the eastern balcony for tranquil morning views across the golf course. In this secure, modernized building, residents enjoy covered and guest parking, private storage, and a breezeway that connects both towers — enhancing the sense of community. Amenities abound: a Gulf-front heated pool and spa surrounded by a paver-brick sundeck, a well-equipped fitness center, and attentive on-site management and staff. A $12 million renovation in 2008 brought new impact-rated windows, roofing, exterior resurfacing, spa and pool enhancements, paver decks, and refreshed lobbies and fitness facilities. The 2015 plumbing project further modernized the infrastructure with new domestic water piping and lining. Every detail has been considered, offering peace of mind and timeless appeal. This is truly an owner’s retreat. Just beyond your door lies The Links on Longboat, a spectacular seaside golf course reimagined for today’s player — a par-71 layout spanning 6,748 yards of beautifully maintained greens. Membership options at the Longboat Key Club provide access to a second Harbourside course, world-class tennis, fine and casual dining venues, a full-service spa and fitness center, club gatherings, concierge services, and The Longboat Key Club Moorings — a deep-water marina offering exclusive affiliation opportunities. Living on Longboat Key is more than a lifestyle — it’s a privilege. With fine dining, boutique shopping, and cultural attractions just minutes away at St. Armands Circle and downtown Sarasota, this location perfectly blends resort-style living with everyday convenience.
Listing Agent: Judy Kepecz-Hays (941-587-1700)
3060 GRAND BAY BLVD #174, LONGBOAT KEY, FL 34228
$1,939,00099 Days on yellowkey MLS ID: R4910478
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2550 Built: 1994Monthly Fee: $2,617 Tax: $17,500 (2024)Community: Grand Bay 1Condo
Taxes:$17,500
Tax Year: 2024
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)
1281 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$1,050,00015 Days on yellowkey MLS ID: A4688079
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 1999 Tax: $9,956 (2025)Community: Water Club 01 At Longboat KeyCondo
Taxes:$9,956
Remarks: Welcome to a little piece of paradise on Longboat Key at the stunning gated Gulf-front condominium community of Water Club, which offers a coastal lifestyle complete with direct access to sandy beaches, high-end amenities and exceptional security and concierge services. This designer-inspired, furnished two-bedroom, 2.5-bath condominium is on the newer north building's plaza level and features nearly 1,400 square feet, 10-foot ceilings, double crown molding, plank wood flooring in the living areas, natural colors and floor to ceiling storm impact windows and doors. An open floor plan offers garden views from the spacious living room and the kitchen, which has both a breakfast bar and a seating area. A beautiful kitchen renovation was completed in December 2025 with handsome wood cabinets, stone countertops and GE Profile appliances. The split plan allows privacy for owners and guests in the two separate primary en-suite bedrooms, each with large windows, custom drapes and carpet, wall closets with built-ins and baths with combination tub/showers. ?An expansive balcony with glass railing barriers can be accessed through the living area and one of the primary suites. This lovely condo conveniently has a stack washer and dryer, linen closet, underbuilding storage unit and assigned parking and its own front desk concierge. Behind the 24-hour guarded-gate is true luxury living with a modern clubhouse, state-of-the-art fitness room, locker room and spa, sauna, bar and lounge, library, game room, ballroom and catering kitchen and outside terrace for gatherings and watching sunsets over the Gulf waters. Besides the magnificent beach and Florida-friendly landscaped grounds, the outdoor amenities include a peaceful courtyard, fire pit, resort-style pool and hot tub and new Har-tru tennis courts. Water Club is conveniently near island golf courses and Publix, and a short distance from St. Armands Circle and downtown Sarasota for dining, shopping, entertainment and cultural venues.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kathleen Ucci (941-302-2344)
2165 GULF OF MEXICO DR #115, LONGBOAT KEY, FL 34228
$2,350,00045 Days on yellowkey MLS ID: A4684194
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2485 Built: 1996 Tax: $12,382 (2025)Community: Villa Di Lancia Ph 1Condo
Taxes:$12,382
Remarks: Experience and enjoy breathtaking, unobstructed Gulf views from this exceptional “walk-down” corner 3-bedroom 3-bath residence in the prestigious Villa Di Lancia community on South Longboat Key. Fully updated and spanning 2,485 sq. ft., this residence feels like its own private beachfront home. Upon entering from the semi-private elevator lobby, you are welcomed into an open and light-filled floor plan with soaring 10-foot ceilings and expansive walls of glass. As one of the most desirable corner residences in the community, this residence showcases panoramic Gulf views from nearly every room, which can be enjoyed by an additional wall of windows that flood the interior with natural light. The expansive great room connects to a nearly 500 sq. ft. covered terrace — your front-row seat to spectacular sunsets over turquoise waters! The terrace also has a private staircase allowing direct access to the beach and Gulf-front pool and spa, creating a rare and seamless indoor-outdoor lifestyle. The updated eat-in kitchen features a serving bar, walk-in pantry, full laundry room, and generous storage. The split floor plan allows owners and guests alike to enjoy quiet privacy. The primary suite is a true retreat, complete with direct Gulf views, private terrace access, spacious closets, and a large en-suite bath. The guest wing includes a second en-suite bedroom, as well as a third bedroom or a convenient and flexible den space with an adjacent bath. Villa Di Lancia is an exclusive boutique community with only 38 residences with resort-style amenities. Relax by the heated Gulf-front pool and spa, or enjoy friendly competition on the Har-Tru tennis and pickleball courts, as well as a state-of-the-art fitness center and steam room. Resort-style living has been effortlessly achieved throughout the community, including the newly updated clubhouse, social room and kitchen, on-site management, 24-hour manned gate, EV charging station, secure under-building parking, guest parking, and a private storage room. This welcoming community is both pet-friendly and impeccably maintained. Ideally located on the southern end of Longboat Key, residents enjoy proximity to fine and casual dining, golf, marinas, shopping, St. Armands Circle, and Sarasota’s cultural attractions. Residences here are rarely available. This is a rare opportunity to own a luxurious beachfront sanctuary and experience refined coastal living at its finest. This residence feels like a beautiful private home on the beach!
1241 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$2,795,000168 Days on yellowkey MLS ID: A4669837
Bed: 3 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3045 Built: 1996 Tax: $25,341 (2024)Community: Water Club 01 At Longboat KeyCondo
Taxes:$25,341
Remarks: Welcome to The Water Club at Longboat Key, where privacy, spaciousness, and resort-style amenities complement the natural beauty of the setting at the edge of the sparkling waters of the Gulf of Mexico. Residents benefit from a semi-private elevator that opens directly into an impressive foyer, offering sweeping views of Sarasota Bay and the city skyline through floor-to-ceiling windows. This residence is on the north side of the south building, the sunset view side, overlooking the beautiful pool deck amenity of the community. This eighth-floor Brighton residence is highly coveted for its three-bedroom configuration with panoramic vistas of the Gulf, beach, and bay from two expansive terraces. Features include ten-foot ceilings, extensive glass walls, and storm protection shutters , enhancing both comfort and sophistication. The living room is designed to maximize openness and showcase sunsets over the Gulf. The primary suite offers a private terrace, den, walk-in closet, and dual bathrooms. With a split-bedroom plan, privacy is maintained for two generous guest suites, each featuring an en-suite bath. The kitchen is efficiently appointed with significant storage and a breakfast area overlooking the water. The Water Club stands as Longboat Key’s premier gated beachfront community, situated on 16 acres of meticulously landscaped grounds. Amenities include a 17,000-square-foot clubhouse, well-equipped fitness center and spa, heated lap pool and hot tub, four Har-Tru tennis courts, concierge services, and versatile gathering spaces such as a library, billiards room, ballroom, firepit, and grilling area. Additional conveniences include under-building parking, climate-controlled storage, on-site management, and 24-hour security. Ideally located on the south end of Longboat Key, residents enjoy proximity to Longboat Key Club golf facilities, Publix shopping center, exclusive St. Armands Circle, downtown Sarasota’s cultural offerings, and Sarasota International Airport, just 20 minutes away. The Water Club is pet-friendly and impeccably maintained, providing the pinnacle of coastal luxury living.
Listing Agent: Michael Moulton (941-928-3559)
1211 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
$1,499,000152 Days on yellowkey MLS ID: A4670789
REDUCED by $26,000 (1.7%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1598 Built: 1985 Tax: $14,271 (2024)Community: PromenadeCondo
Taxes:$14,271
Remarks: No matter where you 'summer' you belong in sunny Sarasota for the 'winter'. Feast your eyes on this TURN-KEY FURNISHED, BEACH FRONT condo. Your job? BRING YOUR LUGGAGE ... everything else is here! This lovely Longboat Key condo is beautifully furnished, fully equipped and calling your name. Renovated and reimagined for casual living just a few years ago, it features an open kitchen, gulf front balcony dining, fabulous wet bar and a cozy living room for quiet moments by the fire. The sleeping areas are split for maximum privacy for you and your guests. The primary suite is everything you'd hope for - gulf views from your bed, a truly exceptional ensuite bath, plenty of closet space plus a private make up area. The guest room is comfortably furnished, quiet and also offers its own view. Tile flooring throughout, full size laundry equipment, storage galore, custom window coverings and so much more. This beautiful complex is among LBK's most sought after, thoughtfully designed for resident comfort and security, well managed and impeccably maintained. The unit has been only gently used by its owners and NEVER RENTED, although leasing is ok. The complex provides concierge, private beach access, heated pool and spa, tennis, fitness and sauna areas, community rooms for parties, BBQ, sunny patio and so much more. You'll appreciate a storage locker as well as both an assigned parking spot and plentiful guest parking. 5 minutes to the Longboat Key Club or Publix, 10 minutes to St Armands. 15 minutes to downtown Sarasota. Leave the snow behind ... the sun is shining and it will be 80 degrees today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Sharon Whalen, Pa (941-957-8805)
5055 GULF OF MEXICO DR #331, LONGBOAT KEY, FL 34228
$895,000158 Days on yellowkey MLS ID: A4670624
REDUCED by $90,000 (9.1%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $5,337 (2024)Community: Club LongboatCondo
Taxes:$5,337
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: One or more photo(s) has been virtually staged. Welcome to your coastal retreat in paradise — a stunning third-floor waterfront residence in Club Longboat Beach and Tennis, offering expansive Gulf views and one of the largest floor plans in the community. This exceptional 2-bedroom plus 3rd bedroom/study layout perfectly blends elegance, comfort, and functionality, ideal for full-time living or as a refined vacation escape. With 750 feet of pristine Gulf frontage, this home immerses you in the beauty and serenity of coastal living. Beautiful engineered white oak wood floors flow throughout the open, sun-filled living space, which seamlessly extends to your private balcony’s, the perfect spot to enjoy the tranquil sound of the waves and stunning sunsets. The updated kitchen features stone countertops, white cabinetry, and has been opened up to create a larger, more connected floor plan ideal for entertaining. The primary suite is a private sanctuary, boasting a remodeled marble bath with high-end fixtures and a spa-like ambiance. The guest suite provides equal comfort and privacy, featuring a beautifully appointed travertine-floored bathroom. A custom wall of California closets offers exceptional storage and style. The Club Longboat Beach and Tennis community offers amazing amenities, including private beach access with lounge chairs and beach umbrellas, eight professional har-tru tennis courts, pickleball, fitness center, shuffleboard, barbeque area, clubhouse with regular social events, sauna, spa and two heated swimming pools. Club Longboat is a pet-friendly community allowing up to two pets with fees that include exterior maintenance and insurance, cable, water, sewer and trash. Perfect as a full-time residence or an income-producing rental, with one-month minimum leases permitted up to 12 times per year. Only a short drive to many fine restaurants, boutiques, Anna Maria Island, St. Armands Circle and the City of Sarasota. Sarasota is a well-known center for arts and culture including the Asolo Theater, Van Wezel Performing Arts Center and Ringling Museum. Schedule your showing today and make resort style living a reality.
Listing Agent: Ryan Heers (941-726-1703)
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000285 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceCondo
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)
4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$649,90082 Days on yellowkey MLS ID: A4679160
REDUCED by $10,000 (1.5%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,738 (2025)Community: Windward Bay AmdCondo
Taxes:$7,738
Remarks: SELLER SAYS “SELL!” Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. From dolphins at dawn to sunsets on the Gulf—every day is paradise. 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, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.
Listing Agent: Debby Mccaig (941-544-1713)
360 GULF OF MEXICO DR #312, LONGBOAT KEY, FL 34228
$1,100,000106 Days on yellowkey MLS ID: A4676411
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2298 Built: 1992 Tax: $13,341 (2025)Community: Tangerine Bay ClubCondo
Taxes:$13,341
Remarks: Tangerine Bay Club An Island Resort-style condo located at the premier location on Longboat Key. This professionally painted 2 bedroom, 2.5bath with office/den features views of Sarasota Bay. It is in close proximity to New Pass and the pristine beaches of the Gulf of Mexico. Upgraded Ergon Fall White stone ceramic tile flooring is as beautiful as it is durable. The kitchen will satisfy your culinary desires an features; European cabinetry, lavish corian counters, Ge Profile Stainless steel appliances, Gas cooktop including an 18-bottle wine cooler and double oven. The chef's kitchen desk space will help you plan your extravagant meals. It is conveniently located near the breakfast nook and view of your courtyard. The open floor isilluminated by natural direct and indirect sunlight. Catch breathtaking sunrises over Sarasota Bay or relax by the gas fireplace during the winter. Hang out on the patio enjoying your favorite beverage and enjoy the lush exotic view. Mahogany doors through the residence give the condo a splendid feel. Stay cool all summer long with the brand- new Comfort Maker A/C unit that was just installed. Cleanses and refresh in your spa-like remodeled master bathroom with a new vanity, separate sinks, new toilet, new jacuzzi tub, tile quartz counters, and spacious neutral tile shower. Come enjoy the outrageous serenity of a LBK sunset. Maybe you will be lucky enough to witness a Flash of Green or Bioluminescence lights. Tangerine Bay offers resort-style amenities centered around one of the luxurious private pools on all of Longboat Key. The amenities include a cabana, fitness center, library, hot tub, and pool surroundedby tropical landscape. The resort also features tennis courts, pickleball courts, and a clubhouse. Organized social including group happy hours in the Cabana, scheduled group pickleball games, and planned excursions to local cultural happenings. Come hang out at Your Private Beach Access at Bay Isles Beach Club for only $250 per year. The privacy and island feel of Tangerine Bay is highlightedby its Bay front living enjoy the recently renovated boat dock which is a secret fishing spot or slip into your kayak and launch out for some peace and serene calm. Longboat key is one of the top destinations for enthusiasts of golf, tennis, fine dining, world-class fishing, and boating. In addition, Tangerine Bay Club is positioned at the southernmost point of theisland, walking distance to Quick Point Nature Preserve located on the New Pass and Sarasota Bay. Come check out all the tropical birds and enjoy a stroll through the nature path. Bring your fishing pole or picnic lunch. Tangerine Bay is located across from the famous Longboat Key Club Golf Course . Come enjoy fine dining in downtown Sarasota, St Armands Cir, or many highly rated island restaurants.Just over the bridge is City Island, Mote Aquarium, Ken Thompson Park, and Sarasota Sailing Squadron marina. The St. Armand's Circle shopping district and Lido Key Beach are just a few minutes drive.
Listing is courtesy of: SUNREAL ESTATE INC (941-376-7653)
Listing Agent: Karl Helbig (941-376-7653)
3810 GULF OF MEXICO DR #F206, LONGBOAT KEY, FL 34228
$325,00019 Days on yellowkey MLS ID: A4686238
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1007 Built: 1970 Tax: $3,657 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,657
Remarks: Start living the Longboat Key lifestyle from day one in this furnished coastal condominium at Beach Harbor Club with serene bay views. This spacious two bedroom, two bath residence is ideally located in a sought after beach to bay community along Gulf of Mexico Drive. Positioned on the second floor with convenient elevator access, the residence is filled with natural light and offers a comfortable, easy flowing layout. The living and dining areas feel bright and inviting, with soft views of Sarasota Bay creating a calm, coastal backdrop. Beautiful luxury vinyl flooring extends throughout much of the residence, adding a fresh and cohesive feel. The kitchen provides ample space and storage, features an InSinkErator replaced in 2024, and a separate laundry room with a Maytag stackable washer and dryer adds everyday convenience. Both bedrooms are generously sized and well situated, with the primary bedroom being ensuite. Both bathrooms feature tubs, offering comfort and flexibility for owners and guests alike. A 2 ton Trane HVAC system installed in 2024 adds significant value and peace of mind. All furniture and furnishings are included, making this a truly move in ready opportunity. The residence experienced no damage or flooding from recent storms. Beach Harbor Club stretches from the Gulf to Sarasota Bay, offering the best of both worlds with a private deeded beach for stunning sunsets and Bayfront amenities include a marina with fishing pier, kayak storage. The community also features a heated pool, cabanas and grilling and picnic areas, a clubhouse, and a fitness center. Covered carport parking is included. You are a short drive to SRQ airport, with easy access to nearby beaches including Siesta Key, Lido Beach, and Anna Maria Island, as well as the shopping, dining, and boutiques of St. Armand's Circle and the vibrant downtown Sarasota scene. Simply arrive, unpack, and start enjoying your place in the sun.
Listing Agent: Pam Bailey (941-777-5039)
4900 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$698,000158 Days on yellowkey MLS ID: A4671087
1 Days Off yellowkey (back on 2/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1312 Built: 1975 Tax: $6,787 (2024)Community: Windward BayCondo
Taxes:$6,787
Remarks: Under contract-accepting backup offers. Breathtaking full bay views greet you as you enter this delightful 2 Bedroom 2 bath condo at Windward Bay. The interior has been freshly painted and fully updated with brand new Luxury Vinyl Plank flooring and Moen plumbing fixtures. The Unit boasts granite countertops and Brookhill custom wood cabinets in kitchen and baths, GE Profile double oven, Bosch stacking washer/dryer, Hunter Douglas window treatments, large walk-in master bed closet, hurricane impact windows, and Honeywell WiFi thermostat with humidity control. Enjoy the stunning waterfront views as you dine or relax on your private lanai. Windward Bay is a low density, pet friendly community nestled on 26 acres with 1/2 mile of waterfront trails and 3 adjacent beach accesses. (1deeded,2public). It enjoys a prime mid key location near dining, shopping, and world class entertainment in St Armand's Circle, Sarasota, and Anna Maria Island. The property has many recent updates including new roofs, painting of the mid-rises and extensive landscaping. Its numerous amenities include 2 heated pools, tennis and pickleball courts, 2 marinas with 28 boat slips, kayak racks and launches, covered parking, grills, firepits, and seating areas throughout, and a clubhouse with kitchen, meeting room, fitness center, 2 saunas, and a library. One of the very few units at Windward Bay with ALL of its assessments having been fully paid, including the 15 year Community Capital Improvement and the 30 year Longboat Key undergrounding. For added security, the State of Florida Milestone Inspection on all buildings is complete and Windward Bay is certified for an additional 10 years. Whether your're considering a getaway, a new home, or a rental property, don't miss this great opportunity to own your piece of paradise.
Listing Agent: Richard Perlman (941-228-8580)
4350 CHATHAM DR #106, LONGBOAT KEY, FL 34228
$409,00021 Days on yellowkey MLS ID: A4687361
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $2,272 (2025)Community: Longboat HarbourCondo
Taxes:$2,272
High School: Manatee High
Middle School: W.D. Sugg Middle
Remarks: Light, bright, charming and ready to move into! Kitchen gutted to studs, totally updated. Tile floors, lots of closet space throughout. Updated baths, Enclosed Lanai with tile floors and electric shades overlooks lovely water view. Lovely updated decor. Furnishings are negotiable . Longboat Harbour is amenity packed- 4 heated pools, tennis/pickleball, At the clubhouse/communinity center there is a full equipped gym with sauna and lockers, library, wood shop, kayak float/launch, social room, billiards room, shuffleboard. Great location! The community laundry room and pool are just around the corner and this unit in Building E has the shortest walk to the deeded beach access across the street, where there are restrooms and showers. Longboat Harbour is a very vibrant community with many social activites. An excellent rental as well. Call me for a showing. No water intrusions post-hurricanes 2024.
Listing Agent: Michael Yawitz (941-587-8091)
3804 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228
$397,00019 Days on yellowkey MLS ID: TB8490120
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1133 Built: 1970 Tax: $3,764 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,764
Remarks: Welcome to your new slice of paradise at the Beach Harbor Club! This gem is located in 'B' building, closest to the Gulf of Mexico, and less than one-minute walk to pristine white sand beach ! "This bright two-bedroom, two-bathroom condo has been thoughtfully updated for 2025 with a brand-new HVAC system and water heater, giving you total peace of mind. Standing out as a unique residence that is 12.5% larger than front-facing units, this south-facing home is drenched in tons of natural light and features a modern open-concept kitchen and living room design. The chef’s kitchen is a true centerpiece, boasting a 14-foot-long center granite counter and custom cabinetry with soft-close drawers and doors. Throughout the entire home, you will find cool-to-the-touch 18-inch travertine tiles on all floors and Bahama shutters on every window, while the primary suite offers a spacious walk-in closet and beautiful views of the Gulf—vistas that can also be enjoyed right from the foyer. Designed for convenience with two separate entrance doors, this condo makes it easy to walk to the beach via your deeded access on the pristine sands of Longboat Key or launch a kayak into the bay right from the community docks. Between the heated pool, fitness center, and sunset views over the water, it feels like a year-round vacation. You’re perfectly placed mid-key, so you can easily bike over to Bayfront Park for a game of pickleball or a walk along the bay trails. With a covered carport, everything is set for you to just arrive and start enjoying the coastal lifestyle—Longboat living truly doesn't get better than this! Schedule your tour today! Come and visit this Beauty, this will not last long!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Sarah Wampler (941-209-0676)
1050 LONGBOAT CLUB ROAD #903, LONGBOAT KEY, FL 34228
$995,000375 Days on yellowkey MLS ID: A4647430
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974 Tax: $13,724 (2024)Community: Privateer NorthCondo
Taxes:$13,724
Remarks: SIGNIFICANT PRICE REDUCTON - This TOTALLY RENOVATED ISLAND BEAUTY will charm the most sophisticated Buyers and the spectacular sunrise views over Sarasota Bay enhanced by sunset-lit City and Golf Course views will take your breath away. Ideally situated within a short beach walk between the popular Resort at Longboat Key Club and the brand-new St. Regis Resort, this perfect gem features storm shutters PLUS impact-rated sliding doors for complete safety & security and to enhance the amazing sunrise to sunset views from its desirable 9th floor location. Taken down to the studs, and perfectly planned to utilize every inch, with all new electrical components and LED lighting, new PVC pipes, solid core doors, custom designed cabinetry thought-out, and so much more, there is nothing left to do but enjoy the island lifestyle from the moment you arrive. The open-concept kitchen makes entertaining a breeze and offers custom solid-wood cabinetry, gorgeous quartz countertops, a Sub-Zero refrigerator, and stylish hi-end Bosch appliances, including a wine cooler. The primary bedroom & living room lead to a separate balcony where you can soak up the sun while enjoying the peaceful island surroundings. BTW - the views from the Primary bedroom are simply spellbinding day and night, and it almost feels as if the trees on the adjacent Golf course are perfectly positioned to dazzle you. Residents enjoy the convenience of the on-site manager, a secure lobby and resort style amenities including tennis and pickle ball, heated pool and spa, a well equipped gym, and the total refurbishment of the lobby, hallways, inviting social room, community bathrooms, showers as well as the new beachfront landscaping which create an even more exceptional experience in this world-class beach location. A membership to Longboat Key Club’s plentiful offerings will provide many hours of outdoor fun and golf enthusiasts will appreciate the two championship courses. A 27-hole course Harbourside & an 18-hole course at Links on Longboat, both meticulously maintained offering stunning scenery. Tennis players can take advantage of 25 Har-Tru tennis courts, while pickleball fans will enjoy the 8 newly added courts. These facilities, along with professional instruction and a well-appointed pro shop, cater to athletes of all levels. Outside the gates, Longboat Key offers a 10 mile stretch of pristine beaches, boating, fishing, and a great variety of local treasures to explore. Fine & casual dining, boutique shopping and Sarasota's many cultural offerings are just moments away, creating the perfect balance of relaxation and activity in this sought-after island paradise.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
3070 GRAND BAY BLVD #632, LONGBOAT KEY, FL 34228
$724,900526 Days on yellowkey MLS ID: A4627468
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1276 Built: 1995 Tax: $7,802 (2024)Community: Grand Bay 6Condo
Taxes:$7,802
Remarks: Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace offering sunrise and sunset views. This particular condo has been tastefully updated with new variable speed HVAC with humidity control & Wi-Fi thermostat in 2024; new water heater & significantly updated kitchen in 2026; new refrigerator, washer & dryer, Hunter Douglas battery operated remote-controlled window treatments, lighting & plumbing fixtures & freshly painted all in 2023. Nothing more to do but to move in and enjoy everything Grand Bay, Longboat Key and Sarasota have to offer especially with the recently renewed transferable Home-Tech service contract! Your amenities include two large resort style heated swimming pools and spas, tennis courts, state of the art fitness center and expansive clubhouse with social activities as well as access to the private white sandy well maintained beach at the Bay Isles Beach Club on the Gulf of Mexico. You will also have access to beautiful peaceful walking trails winding along the bay front, marina and golf courses. A short drive will lead you to choice eateries along Gulf of Mexico Drive or over the bridge to St Armands Circle and downtown Sarasota.
3040 GRAND BAY BLVD #213, LONGBOAT KEY, FL 34228
$1,550,00084 Days on yellowkey MLS ID: A4678941
Bed: 2 Bath: 3.5 Liv Area Sq Ft: 2550 Built: 1996 Tax: $8,474 (2025)Community: Grand Bay 2Condo
Taxes:$8,474
Remarks: Beautifully positioned within Grand Bay on Longboat Key, this 2-bedroom + den residence offers 2,550 sq ft of light-filled living with a private elevator opening directly into the home. Expansive Sarasota Bay views, two generous terraces, and seamless indoor–outdoor flow create an ideal setting for sunsets, bay breezes, and relaxed coastal living. Set behind the gated Bay Isles entrance, residents enjoy resort-style amenities, deeded beach access, and a lifestyle defined by location, comfort, and waterfront elegance. The spacious primary suite offers a tranquil retreat with direct terrace access, peaceful water views, a large walk-in closet, and a spa-like bath featuring dual vanities, a soaking tub, and a walk-in shower. The generous kitchen featuring a Sub-Zero refrigerator and causal eat-in dining, den, and guest suite each open to a second terrace that overlooks Bay Isles’ beautifully landscaped grounds and tennis courts. The den offers versatility for a home office or additional living space, while the guest suite features an en-suite bath and private access to the expansive terrace. A dedicated wine and storage room adds a thoughtful layer of convenience and elegance, blending seamlessly into the home’s well-planned layout. Grand Bay residents enjoy an array of resort-style amenities, including two pools, a fitness center, tennis courts, a clubhouse, and deeded beach access through the Bay Isles Beach Club. Set behind the secure gates of Bay Isles, this residence offers the perfect blend of space, privacy, and the coveted Longboat Key lifestyle.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
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