Location: Longboat Key
Do Not Show Listings
225 SANDS POINT RD #7101, LONGBOAT KEY, FL 34228
$699,00092 Days on yellowkey MLS ID: A4678918
3 Days Off yellowkey (back on 3/30/2026)
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $7,270 (2025)Community: Inn On The Beach Ph IiiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,270
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Under contract-accepting backup offers. Enjoy peaceful lagoon views from this completely remodeled Junior Suite. Sold turnkey furnished and currently in the hotel program, the Junior Suites in this building have 10’ ceilings unlike the other buildings. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace. As an owner in the hotel program you are able to take advantage of the amenities offered by the 410 acre member-only Longboat Key Club while using your owner time. These include fine dining in 5 exclusive restaurants, 45 holes of Championship Golf, the award-winning Tennis Gardens, spa, fitness center, white sand beach with umbrellas & waitstaff, and a full service marina. The renovated rooms, main dining area, pool and guest services provide an enhanced product and elevated experience to a property that already accumulates a multitude of awards including the AAA Four-Diamond Award and Condé Nast Travelers Top Florida Resorts. Start enjoying your Longboat Life today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
3240 GULF OF MEXICO DR #B104, LONGBOAT KEY, FL 34228
$495,00011 Days on yellowkey MLS ID: A4688243
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1975 Tax: $4,538 (2025)Community: PortobelloCondo
Taxes:$4,538
Remarks: Experience tranquil island living in this beautifully maintained first-floor residence at Portobello, offering private, serene views of expansive grounds, lush mangroves, and the bay. With your beach, shimmering Gulf waters, and breathtaking sunsets just across the street, this is the perfect coastal retreat. Designed with a desirable split floor plan, the home is filled with natural light from sliding glass doors that span the width of the residence. The large screened-in lanai is accessible from the living area and both bedrooms—seamlessly blending indoor and outdoor living while overlooking a generous grassy yard space and peaceful bayou, perfect for canoeing and kayaking right from your backyard. The kitchen features granite countertops and stainless steel appliances. Offered turn-key and fully furnished, this residence is move-in ready and ideal for seasonal or full-time living. Portobello is a sought-after Beach-to-Bay community ideally located mid-Key, offering an exceptional array of amenities including 600 feet of private beach frontage and 260 feet along the bay. Residents enjoy a heated community pool, tennis courts, clubhouse, BBQ and picnic areas, fishing pier, and kayak launch. Just minutes from the world-class shopping and dining of St. Armands Circle and everything Sarasota has to offer, this exceptional residence invites you to experience the pinnacle of Longboat Key living—where every day feels like a vacation.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
6700 GULF OF MEXICO DR #117, LONGBOAT KEY, FL 34228
$550,0007 Days on yellowkey MLS ID: A4687787
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1969 Tax: $2,348 (2025)Community: Whitney BeachSpa: NoCondo
Taxes:$2,348
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Welcome to 6700 Gulf of Mexico Drive #117, a beautifully reimagined end-unit 2-bedroom, 2 full bath residence in the sought-after Whitney Beach community on Longboat Key. Taken down to the studs and completely renovated, this waterfront condominium offers coastal living with sweeping views of Bishop’s Bayou, abundant natural light, and exceptional privacy. A private front courtyard welcomes you inside, where new high-end luxury vinyl plank flooring flows throughout, and a bright, open layout immediately draws your eye to the water. As an end unit, additional windows enhance the airy feel, while hurricane-impact windows and sliding doors frame tranquil bayou views. From the main living space—and even from the primary bedroom upon waking—you’ll enjoy peaceful scenes of dolphins, manatees, and glowing sunsets reflecting across the water. The fully redesigned kitchen is both stylish and functional, featuring granite countertops, soft-close cabinetry, custom glass-front accents, classic subway tile backsplash, designer pendant lighting, peninsula seating for four, and a full suite of GE stainless steel appliances—all positioned to capture the water views. Both bathrooms have been completely renovated with glass walk-in showers, elegant tilework, and quartz-topped vanities, offering a clean, modern aesthetic. A new Whirlpool stackable washer and dryer adds everyday convenience. Whitney Beach is a unique beach-to-bay community with deeded private access to the Gulf just across the street. Residents enjoy resort-style amenities including pools, tennis courts, shuffleboard, barbecue areas, kayak storage and launch, walking paths, and a tranquil bayfront pavilion. Boat slips are available when offered, and the community pier provides a charming setting for fishing or relaxing by the water. Ideally located on the north end of Longboat Key, this residence offers easy access to Anna Maria Island, as well as the dining, shopping, and cultural attractions of Sarasota. Whether as a full-time home, seasonal retreat, or investment, this is an exceptional opportunity to enjoy the best of bay-to-beach living. Professional photos coming soon.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kelly Sallee (941-914-0400)
6700 GULF OF MEXICO DR #139, LONGBOAT KEY, FL 34228
$485,000133 Days on yellowkey MLS ID: A4674675
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1305 Built: 1969 Tax: $4,551 (2024)Community: Whitney BeachCondo
Taxes:$4,551
Tax Year: 2024
Remarks: PRICED BELOW MARKET VALUE AT $499,000 ! Fully renovated 2 Bedroom 2 Bath Whitney Beach Bay Side FIRST FLOOR condo ready for occupancy. It has undergone FEMA approved storm mitigation & has had a full rebuild & inspections. All new handsome Luxury Vinyl Plank flooring throughout plus tile in the primary bedroom’s stunning en suite with shower & 2nd bathroom with tub. Large, impact resistant sliders in the lanai area overlooking the canal waterfront & living room area & front door have been installed. A brand new kitchen was installed with quartz counters, custom cabinetry, stainless steel refrigerator & stove & new overhead lighting fixtures in every room. This like new & totally improved condo offers almost 1,500 square feet of interior living space plus a storage room at the entry which has a new stackable washer & dryer. Whitney Beach Bay Side offers two heated pools, kayak launch & storage, boat slips, fishing docks & a charming boathouse overlooking serene Bishop’s Bayou which leads to Sarasota Bay. This rental friendly community allows minimum of one month rentals, six times a year. It is also pet friendly allowing large dogs one of very few on Longboat Key. On the deeded beach access/Gulf of Mexico side, there is the Whitney Beach Conservancy land owned by the condo association for the use of owners, tenants & guests. Tennis & pickleball courts, a barbecue & picnic area & tike huts lead to the gorgeous sandy beach where you will enjoy swimming, sunning, shell collecting , and gatherings with neighbors while watching the most stunning sunsets you will ever see!
Listing Agent: Maruta Miluns (941-374-9702)
3427 WINDING OAKS DR #14, LONGBOAT KEY, FL 34228
$1,150,00029 Days on yellowkey MLS ID: A4686623
0 Days Off yellowkey (back on 4/16/2026)
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: Under contract-accepting backup offers. 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 is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Carolyn Donnelly, Pa (941-350-9900)
3806 GULF OF MEXICO DR #C310, LONGBOAT KEY, FL 34228
$389,00013 Days on yellowkey MLS ID: R4911020
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,457 Tax: $2,813 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,813
High School: Booker High
Middle School: Booker Middle
Remarks: Longboat’s Beach Harbor club is situated on 5 Acres along the most beautiful stretch of Longboat Key Shoreline. Sugary sand and flowing seaoats beside the azure blue Gulf of Mexico. The beach Harbor club offers 133 condo units, deeded beach access with showers, umbrellas and beach chairs. Amenities also include newly constructed boat slips, rooftop decks, outdoor cook areas, heated oversized swimming pool, community area for kayaks, clubhouse, and shuffle board. Longboat Beach Harbor is a friendly community with group events and many fun times to build relationships and enjoy sense of community living. Close to Bayfront Park with Tennis, Publix/CVS shopping. This renovated condo is situated on the 3rd floor not requiring flood insurance. Air conditioned indoor hall-way with security entrance. Newly appointed appliances, bathrooms, HVAC, luxury flooring and trim. Up-scale appointed fixtures and details throughout.
Listing is courtesy of: LEN SCAVRON (908-304-5454)
Listing Agent: Len Scavron (908-304-5454)
779 SAINT JUDES DR N, LONGBOAT KEY, FL 34228
$479,000279 Days on yellowkey MLS ID: O6326464
REDUCED by $13,000 (2.6%) on 04/16/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 882 Built: 1972 Tax: $5,814 (2024)Community: Villa Dos PalmasCondo
Taxes:$5,814
Remarks: PRICED TO SELL ! Coastal Elegance Meets Effortless Island Living in Longboat Key Experience the ultimate Gulf Coast lifestyle in this beautifully maintained 2-bedroom, 1.5-bath canal-front residence, perfectly positioned within one of Longboat Key's most desirable waterfront communities. Whether you're searching for a full-time sanctuary or a refined seasonal retreat, this exceptional property delivers comfort, style, and location in perfect harmony. Inside, a thoughtfully updated kitchen takes center stage-featuring brand-new appliances, sleek contemporary countertops, and modern cabinetry designed for both everyday living and effortless entertaining. Solid block construction offers durability and peace of mind, while the newer roof enhances long-term value and security. Step outside and immerse yourself in true island living. With deeded beach access just moments away, you can transition from morning coffee to toes-in-the-sand within minutes. Enjoy leisurely strolls to some of the island's most beloved dining destinations, including Harry's Continental Kitchens, Solorzano's Pizzeria, Lazy Lobster, Lo' Key Island Café, and the iconic Euphemia Haye Restaurant. The property also includes a private 1-car carport and dedicated exterior storage-adding convenience to coastal charm. Perfectly situated on a generous canal-front lot, this residence is a short walk to the sparkling waters of the Gulf of Mexico and only 15 minutes from the sophisticated boutiques and fine dining of St. Armands Circle. Wake to peaceful bay breezes. Spend your afternoons basking on pristine white sands. End each day with spectacular Gulf sunsets painting the sky in gold and coral hues. This is more than a condo-it's a lifestyle. Don't miss your opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: BROKERS REAL ESTATE GROUP INC (407-770-1464)
Listing Agent: Alessandro Rosa (407-460-6589)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500201 Days on yellowkey MLS ID: A4667037
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2394 Built: 1992 Tax: $9,083 (2023)Community: Tangerine Bay ClubCondo
Taxes:$9,083
Tax Year: 2023
Remarks: Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing. This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
435 L AMBIANCE DR #L807, LONGBOAT KEY, FL 34228
$3,500,000192 Days on yellowkey MLS ID: A4668015
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2525 Built: 1994 Tax: $29,083 (2024)Community: L Ambiance At Longboat Key Club Ph 02Spa: YesCondo
Taxes:$29,083
High School: Riverview High
Middle School: Pine View School
Remarks: Discover Your Coastal Paradise at L'Ambiance!** Step into a world of instant enjoyment. Nestled along the stunning Gulf of Mexico, L'Ambiance offers you a front-row seat to Sarasota's dramatic sunrises and captivating sunsets. This exceptional corner residence is a rare gem, designed to help you create a lifetime of cherished memories. As you glide off your private elevator into the foyer, prepare to be mesmerized by panoramic views that seamlessly blend the indoors with the stunning outdoors. Meticulously crafted by a professional decorator, this residence is a masterpiece of elegant living, featuring expansive glass walls that invite the beach's natural beauty into your home. Enjoy the custom kitchen and luxurious bathrooms, all adorned with travertine flooring in the main living areas and plush carpeting in the bedrooms. Imagine sipping your morning coffee on the east terrace, soaking in the breathtaking sunrise, or toasting to the magical afterglow of sunset with a glass of champagne on the southwest terrace. This spacious 2-bedroom (plus den or 3-bedroom) and 3.5-bathroom residence exemplifies the pinnacle of beachside luxury. Your maintenance fee ensures a stress-free lifestyle, covering everything from the building's exterior and cable service to flood insurance and on-site management so that you can immerse yourself fully in the extraordinary island living experience. With concierge services, a resort-style pool and spa, guest suites for visitors, and a state-of-the-art fitness center, L'Ambiance offers amenities that elevate your everyday life. Sarasota's pristine white, sugar-sand beaches are just the beginning! Dive into a vibrant cultural scene to enjoy the Sarasota Opera, the Sarasota Ballet, and the West Coast Symphony. Explore the renowned Ringling Museum of Art, wander through charming art galleries and antique shops, or indulge in exquisite dining at world-class restaurants. Whether you crave the excitement of marinas and golf courses or the casual charm of local cafes, Sarasota truly has it all. Make this luxurious beachfront residence your new home and embrace the unparalleled lifestyle that awaits you at L'Ambiance. Your dream of extraordinary living is just a step away!
3810 GULF OF MEXICO DR #F206, LONGBOAT KEY, FL 34228
$325,00026 Days on yellowkey MLS ID: A4686238
5 Days Off yellowkey (back on 4/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1007 Built: 1970 Tax: $3,657 (2025)Community: Beach Harbor ClubCondo
Taxes:$3,657
Remarks: Under contract-accepting backup offers. 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)
4234 GULF OF MEXICO DR #Q2, LONGBOAT KEY, FL 34228
$648,800406 Days on yellowkey MLS ID: A4643486
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $6,219 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$6,219
Remarks: Beautiful, custom 2024 renovated second floor two bedroom, two bathroom Pelican Harbour & Beach Club condo with panoramic Sarasota Bay views plus Deeded Beach access right across the street. Stunning water views across Sarasota Bay are yours from the Great Room, the Primary Bedroom & from your waterfront, covered & screened in Balcony. Entertain your guests here or enjoy your own private dining outdoor lanai. Almost everything is new & improved in this open concept, sunny & bright home from updated electrical to new impact resistant hurricane proof sliders & windows throughout. You’ll really enjoy the large new window in the kitchen with great views of the pool so you can keep an eye on family & grandchildren. The totally redesigned kitchen features all new custom raised panel cabinetry with soft close drawers, light gray with graining Quartz center island & kitchen counters, Frigidaire Gallery induction cooktop, white subway tile back splash & built in Whirlpool microwave & oven. Newly installed Luxury Vinyl Plank flooring is 9” wide plank in a light oak color. Other improvements include a wine refrigerator, a n HVAC system installed in 2023 plus a new roof on this building in 2024 & exterior painted in 2024. The Sellers have invested close to $100,000 to accomplish this stunning remodel. The open floor plan features a large Great Room which includes the dining area & the living room with several couches plus a double bed size Murphy bed attractively hidden between two built in bookshelves & cabinetry for extra sleeping accommodation. The generous sized Primary Bedroom with En Suite bath has serene waterfront Bay views with sliders opening to the screened in balcony. The En Suite features dual sinks, a custom walk-in tub/shower combo & a Toto toilet. The second guest bedroom is bright & comfortable with an adjoining bath with a shower. Bonus feature of the in unit laundry room is a full size LG high efficiency washer & dryer. There is abundant storage room in this unit especially in the number of new kitchen cupboards, storage areas & closets. Assigned storage lockers are also available in the mail room. Pelican Harbour & Beach Club condominium complex offers one of the best Amenity packages on Longboat Key including 200 feet of private deeded beach with new lounge chairs and beach side bathroom, resort style heated pool, adjoining clubhouse, marina with newly built boat docks and fishing docks for boats up to 28 feet with Sarasota Bay frontage of 800 feet, kayak storage & launch area and is large dog/pet friendly complex plus has tennis & pickleball courts which have recently been renovated & painted. On site maintenance staff plus a professional management company, funded reserves and has successfully passed its milestone inspection for the beach side midrise condo building plus has installed brand new roofs & hurricane rated carports. None of the units in this building sustained any damage from hurricanes Helene or Milton or had any water intrusion. Pelican Harbour’s perfect location at Mid Key Longboat is close to all the best restaurants & shops on Longboat Key and Bay Front Park which offers walk in pickleball games, tennis courts, dog park areas plus an exercise/fitness classes building.
2301 GULF OF MEXICO DR #43N, LONGBOAT KEY, FL 34228
$1,000,00039 Days on yellowkey MLS ID: A4686190
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $10,915 (2025)Community: Islander Club Of LongboatCondo
Taxes:$10,915
Remarks: One or more photo(s) has been virtually staged. Perfectly positioned in the sought-after Islander Club Condominium, this 2-bedroom, 2-bath residence offers commanding Gulf and beach views from the living room, dining room, and both bedrooms. Expansive windows frame the sparkling waters of the Gulf of Mexico, creating a breathtaking backdrop for everyday living while showcasing spectacular sunset skies each evening. Situated front and center on the 4th floor, the residence enjoys one of the most desirable vantage points in the building, elevated enough for panoramic shoreline views yet close enough to feel immersed in the beauty and rhythm of the beach below. Competitively priced, the condominium presents a rare opportunity for the next owner to create their own vision of coastal living. Whether designing a sophisticated modern retreat or a relaxed island escape, the residence offers a blank canvas ready to be transformed to your personal taste and style—truly a chance to make it your own. Residents of the Islander Club enjoy a collection of resort-style amenities including direct access to the pristine Gulf Beach, a beachfront Olympic size swimming pool, tennis courts, fitness center, clubhouse, library, and beautifully landscaped tropical grounds. Located on the coveted south end of Longboat Key, the community offers convenient access to Publix, the world-class shopping and dining of St. Armands Circle as well as the vibrant arts, cultural venues, and waterfront restaurants of downtown Sarasota. Go ahead – Make it your own and have it your way!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Steve Nursey (941-356-7010)
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000162 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)
5125 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$725,000393 Days on yellowkey MLS ID: A4645905
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 961 Built: 1983 Tax: $3,448 (2025)Community: Seagrape InnCondo
Taxes:$3,448
Remarks: An exceptional opportunity to own a private family retreat on the pristine shores of Longboat Key—while generating rental income when you’re away. Located within the intimate beachfront enclave of Sea Grape Inn, this unique resort community offers just eight residences, creating a peaceful, uncrowded atmosphere rarely found on the island. Approved for daily, weekly, or monthly rentals, the property provides excellent flexibility for both personal enjoyment and investment potential. From the moment you arrive, the difference is clear. Each residence is thoughtfully appointed and lives more like a private coastal home than a typical vacation rental. This beautifully maintained condo features stone countertops, updated cabinetry, abundant appliances, and tile flooring throughout. The screened porch serves as a tranquil retreat—perfect for enjoying gentle Gulf breezes, spectacular sunsets, and lush tropical landscaping. Step outside to enjoy the heated beachfront pool overlooking the Gulf—an ideal setting for relaxing swims while taking in sweeping water views. The uncrowded beach is just beyond, with chairs provided for effortless seaside enjoyment. Additional amenities include on-site laundry, a BBQ gazebo area, beach towels, and internet service—everything needed for a seamless coastal getaway. Professional on-site management handles all rentals, marketing, cleaning, bookkeeping, and administrative details, offering truly turnkey ownership with no hidden charges. The residence is being offered turnkey furnished, ready for immediate enjoyment or continued rental success. Ideally situated near local restaurants, nature trails, parks with tennis and pickleball, and convenient shopping, this property combines privacy with accessibility. Financials are available upon request. The condo enjoys strong rental demand; showings will be accommodated with 24-hour notice and guest approval. Please contact the listing agent for availability. Life truly is better on Longboat Key!
775 LONGBOAT CLUB RD #808, LONGBOAT KEY, FL 34228
$2,195,00060 Days on yellowkey MLS ID: A4683021
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2122 Built: 1984 Tax: $17,930 (2025)Community: Beaches Of Longboat KeyCondo
Taxes:$17,930
Remarks: Behind the gates of the Longboat Key Club, this exceptional residence at The Beaches captures sweeping, unobstructed views of the Gulf of Mexico and its pristine shoreline, where vivid sunsets paint the horizon each evening. Perched on the eighth floor, this coveted Star floor plan is ideally positioned as a spacious end residence, offering 2,122 square feet of thoughtfully designed living space with 3 bedrooms and 3 full baths. Walls of glass frame panoramic water vistas and invite natural light to pour into the main living areas. Newly installed impact-rated sliders enhance both storm protection and seamless indoor-outdoor living, while oak engineered hardwood flooring flows beautifully through the living room, dining area, and kitchen, creating a warm yet sophisticated coastal aesthetic. The generous layout provides an effortless blend of comfort and refinement, with well-proportioned bedrooms and baths designed to accommodate both everyday living and gracious entertaining. The Beaches is recognized as one of the premier beachfront addresses within the Longboat Key Club, offering direct access to the sugar-white sands and turquoise waters of the Gulf. Residents enjoy an elevated level of service and amenities, including a 24-hour concierge, resort-style pool, fitness center, tennis courts, and impeccably maintained grounds. Ideally located on the southern end of Longboat Key, this gated community affords convenient access to the fine dining and boutiques of St. Armands Circle, the vibrant arts and culture of downtown Sarasota, and the exclusive offerings of the Longboat Key Club. This is a rare opportunity to secure a front-row seat to the Gulf and embrace the effortless elegance of Florida’s most sought-after coastal lifestyle.
Listing Agent: Lenore Treiman (941-356-9642)
240 SANDS POINT RD #4206, LONGBOAT KEY, FL 34228
$1,115,000200 Days on yellowkey MLS ID: A4667039
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982Monthly Fee: $1,418 Tax: $9,141 (2024)Community: Inn On The Beach Ph IiCondo
Taxes:$9,141
Remarks: This junior suite, located in Building 4, offers spectacular northwest-facing views of the Gulf, providing owners with breathtaking sunsets and expansive water vistas. For those seeking accommodation for larger groups or families, units 4205 and 4206 are conveniently offered for sale next to each other, allowing parties to stay in close proximity. The suite has undergone a complete renovation, ensuring a modern and refreshed living space for its occupants. Currently, the unit is integrated into the hotel program, providing potential owners with a streamlined rental management option. Building 4 itself boasts an advantageous position on the northernmost stretch of the beach, promising a sense of quietude and enhanced privacy away from the main pool areas. Ownership of this suite grants exclusive access to the prestigious member-only Longboat Key Club. This membership unlocks a wealth of amenities designed to elevate the lifestyle experience, even during owner-occupied periods. Culinary delights await at five exclusive restaurants, offering a diverse array of fine dining options. Golf enthusiasts can indulge in 45 holes of championship golf, while tennis players can hone their skills at the award-winning Tennis Gardens. For relaxation and rejuvenation, a state-of-the-art spa and wellness center is available. The pristine white sandy beach is complemented by umbrella service and attentive waitstaff, ensuring a luxurious beach day. Furthermore, a full-service marina caters to boating enthusiasts.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Jackie Kleppinger (941-320-0049)
240 SANDS POINT RD #4205, LONGBOAT KEY, FL 34228
$1,115,000200 Days on yellowkey MLS ID: A4667038
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 640 Built: 1982Monthly Fee: $1,418 Tax: $9,961 (2024)Community: Inn On The Beach Ph IiCondo
Taxes:$9,961
1935 GULF OF MEXICO DR #G7-304, LONGBOAT KEY, FL 34228
$465,00011 Days on yellowkey MLS ID: TB8496217
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: 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)
1000 LONGBOAT CLUB RD #304, LONGBOAT KEY, FL 34228
$874,5006 Days on yellowkey MLS ID: A4689434
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $3,950 (2025)Community: Privateer SouthCondo
Taxes:$3,950
Middle School: Brookside Middle
Remarks: Experience elevated coastal living in this beautifully renovated two-bedroom, two-bath golf-front condominium, ideally situated behind the gates of the prestigious Longboat Key Club in the sought-after community of Privateer South on Longboat Key. Thoughtfully redesigned with a refined coastal aesthetic, this residence showcases a seamless blend of modern elegance and relaxed waterfront living. From the moment you enter, you are welcomed by an open-concept layout filled with natural light, enhanced by expansive windows and tranquil golf course views. The fully updated kitchen features sleek cabinetry, premium finishes, and a clean, contemporary design that flows effortlessly into the spacious living and dining areas—ideal for entertaining guests or enjoying quiet evenings at home. Every detail has been carefully curated to provide both style and functionality. The primary suite offers a serene retreat, complete with a beautifully appointed en-suite bath and generous closet space, while the guest bedroom and bath provide comfort and privacy for visitors. Both bathrooms have been tastefully renovated with modern fixtures and finishes, creating a spa-like atmosphere throughout the home. Residents of Privateer South enjoy a true resort-style lifestyle with an impressive array of amenities. Relax by the sparkling beachfront pool overlooking the Gulf of Mexico, maintain your wellness routine in the fully equipped fitness center, or gather with neighbors in the inviting social room. On-site management ensures ease of ownership and peace of mind. Perfectly positioned between the Gulf and Sarasota Bay, this exceptional property offers convenient access to world-class dining, shopping, and cultural attractions, all while being tucked away in a secure, gated enclave. Whether you are seeking a full-time residence or a luxurious seasonal retreat, this golf-front condominium delivers the very best of Longboat Key living.
2425 GULF OF MEXICO DR #8C, LONGBOAT KEY, FL 34228
$1,550,0006 Days on yellowkey MLS ID: A4688797
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $17,374 (2025)Community: Sea Gate ClubCondo
Taxes:$17,374
Remarks: Welcome to the prestigious Sea Gate community on world renowned Longboat Key! With direct views of the Gulf of Mexico from every room and situated perfectly on the 8th floor, this stunning 2-bedroom, 2-bathroom residence offers just under 1500 square feet of refined coastal living on pristine white shores, endless turquoise waters and vibrant sunsets that create a truly extraordinary backdrop that is postcard worthy! This beautifully appointed residence has been meticulously maintained by the owners and showcases expansive glass sliders that flood the home with natural light, seamlessly connecting the indoor living spaces to a private balcony and your front-row seat to one of Florida’s most coveted coastlines.Thoughtfully enhanced for both comfort and style, the residence features fresh interior paint, a new HVAC system and Hot Water Tank and some new kitchen appliances, delivering a modern and move-in-ready experience. The addition of an in-unit washer and dryer provides a rare and highly desirable level of convenience within the building. The spacious layout offers an effortless flow between the living, dining and kitchen areas for both everyday living and entertaining.The primary suite serves as a peaceful retreat, complete with generous proportions, ample storage and a calming ambiance inspired by the surrounding Gulf views, walk- in closet and ensuite. A well-appointed guest bedroom boasts a private balcony and large closet, while the guest bath provides comfort and privacy for visitors. Residents of Sea Gate enjoy an intimate, resort-style lifestyle with direct beach access, a beachfront pool, tennis courts, a fitness center, and beautifully maintained grounds, all within a private, boutique community setting. Additionally, Sea Gate offers covered parking, ample guest parking and a large storage unit! The building has undergone major capital improvements in recent years, including impact-rated windows (2021), a full exterior restucco and repaint (2022), a new roof (2023) and upgrades to the pool, spa, sundeck and elevator doors. Residents enjoy resort-style amenities including a Gulf front pool and hot tub, fitness center, clay tennis court, library, and a social room with catering kitchen. Shaded tiki huts, outdoor showers, and climate-controlled storage for bikes, kayaks, and paddleboards complete the experience of true beachfront living. All fully paid for by current owners, totaling over $100K/unit. Ideally located near daily shopping, Longboat Key offers a lifestyle defined by elegance and ease, with world-class golf, waterfront dining, boating, and the upscale shops and restaurants of St. Armands Circle just moments away, along with the cultural attractions of Sarasota. With monthly rentals allowed, a unit of this stature could rent for 10k a month in season offering potential income. Option to be sold turnkey furnished as well. Don't hesitate, this unit is a beaut and easy to show!
Listing Agent: Melissa Killion (941-248-6840)
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