Displaying: For Sale
Location: Longboat Key
Property Type(s): Condos
Living Area Square Feet: 1000 to 1499
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Longboat Key - 112 properties found
4500 GULF OF MEXICO DR #3, LONGBOAT KEY, FL 34228
$739,00090 Days on yellowkey MLS ID: A4685838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1325 Built: 1975 Tax: $2,843 (2025)Community: Windward Bay AmdCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$2,843
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: Martha B. King Middle
Remarks: GORGEOUS BAYFRONT PENTHOUSE VIEWS--RARE TOP FLOOR OPPORTUNITY!! Nestled in the heart of a vibrant Longboat Key Community, this stunning two-bedroom, two-bathroom condo offers unparralled water views of Sarasota bay, creating a great backdrop for both sunrises and sunsets. Step inside and be captivated by the breathtaking scenery and spacious design that blends coastal living with sophistication. Beautifully renovated with new floor to ceiling hurricane windows, this condo seamlessly integrates the living and dining areas with an open kitchen featuring stone countertops, custom cabinets and new Stainless steel appliances. The light-filled primary bedroom boasts two closets, one being a walkin complete with built in ample storage. Both bathrooms have been tastefully renovated, offering a spa-like ambiance that invites relaxation. Take in manatee and dolphin viewing from the expansive Florida Room or relax in style looking out the huge picture window as the sun rises over the bay. This professionally managed, pet friendly community offers an array of amenities including 26 acres of landscaped ground, 2 marinas, 2 heated pools, tennis courts, pickle ball courts, state-of-the art Fitness Center, library and Community Clubhouse. Take advantage of the Deeded Beach Access just steps away. With its prime location, stunning views and extensive amenities, this property represents a rare opportunity to embrace the best of waterfront living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Marcela Terrell (941-929-3010)
4350 CHATHAM DR #106, LONGBOAT KEY, FL 34228
$399,00092 Days on yellowkey MLS ID: A4687361
REDUCED by $10,000 (2.4%) on 05/05/2026
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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Yawitz (941-587-8091)
4485 GULF OF MEXICO DR #804, LONGBOAT KEY, FL 34228
$1,025,00065 Days on yellowkey MLS ID: A4690646
REDUCED by $50,000 (4.7%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1175 Built: 1973 Tax: $6,115 (2025)Community: Arbomar AptsCondo
Taxes:$6,115
Remarks: Renovated direct Gulf-front 2BR/2BA on Longboat Key. End-unit 8th-floor condo at The Arbomar, panoramic sunset views, pets allowed, hurricane-protected. For buyers seeking a move-in-ready beachfront residence on Longboat Key, this renovated direct Gulf-front end unit at The Arbomar delivers updated condition and views that don't quit. The 8th-floor 2-bedroom, 2-bath floor plan offers 1,175 square feet, with panoramic Gulf views from the balcony and partial bay views from the bedrooms. Inside, the renovated kitchen features wood cabinetry, quartz countertops, under-cabinet lighting, and stainless-steel appliances. Ceramic tile flooring extends through the main living areas, paired with crown molding, plantation shutters, and custom built-ins. Electric hurricane shutters provide added protection. Recent owner improvements include the renovated kitchen, updated bathrooms, a newer HVAC system, and a tankless water heater. At the building level, The Arbomar has invested in major upgrades including a new roof, hurricane-rated insulated windows, new entry and storm doors, and water-resistant Gemstone concrete coating on lanais and common breezeways. Amenities include a Gulf-front heated pool, fitness room, club room, community kitchen, kayak storage, and climate-controlled storage. The association is well-managed and well-funded, with quarterly HOA fees of $4,000. Rentals are permitted at one-month minimum, four times per year, after the required ownership holding period; pets are permitted for owners, rentals are pet-free. The residence conveys unfurnished, with one assigned carport space. On Gulf of Mexico Drive near island dining, golf, boating, shopping, St. Armands Circle, and downtown Sarasota.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-260-3350)
Listing Agent: Julie Larson, Llc (941-284-9826)
2020 HARBOURSIDE DR #457, LONGBOAT KEY, FL 34228
$724,000Listed 06/23/2026 3:43PM MLS ID: A4696667
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1442 Built: 1984 Tax: $9,366 (2025)Community: Fairway Bay 2 Ph 1Spa: YesCondo
Taxes:$9,366
Elementary School: None
High School: None
Middle School: None
Remarks: Located on the 5th-floor penthouse level of Fairway Bay, this corner 2BR/2BA residence offers beautiful views of Sarasota Bay, the downtown skyline, manicured grounds, pool, and mangrove channels. Garage parking, a rare and desirable feature on Longboat Key, adds to the appeal. From the moment you enter, a wall of sliders draws your eye through the living room to the bay beyond. Tile floors run through the main living areas, and the open layout includes a spacious living room with a flexible bump-out area ideal for extra seating, a reading nook, or workspace. The dining area flows to the kitchen, which features a functional layout, breakfast bar, and adjoining eat-in area with sliders opening to the side terrace. The primary suite offers bay views, built-ins, a walk-in closet, direct terrace access, and a bath with dual vanities, separate water closet, and excellent potential for updating. The guest bedroom is comfortable and includes an en suite bath. The corner terrace extends the living space outdoors, offering a peaceful setting from morning light on the water to the evening glow of downtown. One of the true highlights of Bay Isles living is deeded private beach access through the Bay Isles Beach Club, a resident-only Gulf-front retreat with an on-site attendant, covered gathering and picnic areas, restrooms, changing rooms, barbecue grills, volleyball court, and beach accessory storage. Fairway Bay residents also enjoy 24-hour gated security, tennis courts, fitness facilities, walking paths, and the benefits of Bay Isles living. Optional Longboat Key Club memberships offer access, depending on category, to championship golf, Har-Tru tennis, private dining, beach and pool club facilities, spa, fitness center, wellness studio, club events, and marina amenities. Deepwater slips may also be available separately.
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
$799,000266 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
Tax Year: 2024
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 Agent: Jodene Moneuse, Pa (941-302-4913)
600 SUTTON PL #B302, LONGBOAT KEY, FL 34228
$475,00068 Days on yellowkey MLS ID: A4690036
REDUCED by $25,000 (5.0%) on 04/27/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1132 Built: 1973Monthly Fee: $1,642 Tax: $7,415 (2025)Community: Sutton PlaceSpa: NoCondo
Taxes:$7,415
Remarks: Enjoy the best of the Longboat Key lifestyle in this beautifully updated 2-bedroom, 2-bath waterfront condo at Sutton Place, offering a rare Gulf-to-Bay experience with Sarasota Bay views and PRIVATE DEEDED BEACH ACCESS to a Gulf-front beach just across the street. This light and bright residence features a spacious, open floor plan with quality finishes throughout, including porcelain tile and engineered hardwood flooring for a clean, modern, low-maintenance feel. The updated kitchen is both stylish and functional, showcasing quartz countertops, a mother-of-pearl mosaic backsplash, tray ceiling, and stainless steel appliances. The primary suite includes a fully remodeled bathroom with quartz counters, custom glass shower, and marble tile, while the guest bathroom features granite countertops and a vessel sink. A glass-enclosed and screened lanai extends the living space, bringing in natural light and allowing you to enjoy peaceful bay breezes year-round. Recent upgrades include newly installed IMPACT RESISTANT WINDOWS & DOORS, providing added safety, energy efficiency, and peace of mind. Updated lighting was also added in the living area This residence is being sold TURNKEY FURNISHED, making it truly move-in ready or ideal as a second home or investment property. As an added bonus, the sale includes four brand new KAYAKS—perfect for enjoying the community’s direct bay access and embracing the waterfront lifestyle. Sutton Place is a highly desirable waterfront community offering exceptional amenities, including deeded Gulf beach access with pavilion, gated parking, showers, and picnic areas, TWO heated bayside POOLS, BBQ grills, BOAT SLIPS (first-come, $300/year), kayak storage and launch, fishing dock, clubhouse, and covered parking with ample guest spaces. The community is pet-friendly (2 pets up to 25 lbs each), not age restricted, and allows two rentals per year with a one-month minimum after the first year of ownership, making it ideal for both personal use and investment. Recent community improvements include new roofs, exterior repainting, and resealing (2023), along with a completed milestone inspection. Ideally located mid-key, close to Bayfront Park, dining, shopping, and just a short drive to Anna Maria Island, St. Armands Circle, and downtown Sarasota. Don’t miss this opportunity to own a piece of paradise on Longboat Key.
Listing Agent: Christina Weger (941-773-4154)
546 SPANISH DR S, LONGBOAT KEY, FL 34228
$499,00023 Days on yellowkey MLS ID: A4694824
REDUCED by $10,000 (2.0%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1241 Built: 1966 Tax: $2,488 (2025)Community: Spanish Main Yacht Club CondoSpa: NoCondo
Taxes:$2,488
Remarks: The lifestyle stays premium. The price just got friendlier. Tucked within the waterfront community of Spanish Main Yacht Club on the north end of Longboat Key, this fully renovated detached villa offers a timeless coastal flair just steps from the beach. A true hidden gem and slice of paradise, residents enjoy private deeded beach access to the Gulf of America, a deep water marina with affordable boat slips, and the ultimate boating lifestyle with easy access to waterfront restaurants and open waters. This light and bright 2-bedroom, 2-bath residence is being offered turnkey furnished. Featuring an open floorplan with luxury vinyl plank flooring, impact windows and doors, custom window shades throughout, and a spacious Florida room ideal for additional living or entertaining space. The beautifully updated kitchen showcases quartz countertops, stainless steel appliances, abundant custom cabinetry with soft-close drawers, and a large seating island perfect for gathering. Additional highlights include an interior laundry room with stackable washer and dryer, water softener system, stone paver patio, covered parking, and private driveway. Spanish Main Yacht Club is a vibrant and active 55+ community offering a heated waterfront pool, shuffleboard, social events, pet-friendly policies, maintenance-free living, and one of the most desirable 40-slip marinas on Longboat Key. Ideally located just minutes from St. Armands Circle, Sarasota, and Anna Maria Island, this exceptional Longboat Key retreat is ready for immediate enjoyment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jackie Griese (941-718-0045)
528 FOREST WAY, LONGBOAT KEY, FL 34228
$585,00018 Days on yellowkey MLS ID: A4695863
3 Days Off yellowkey (back on 6/22/2026)
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1440 Built: 1989Monthly Fee: $945 Tax: $3,072 (2025)Community: Cedars East Sec 2Condo
Taxes:$3,072
Remarks: Under contract-accepting backup offers. Elevated, renovated, fully furnished, pet friendly, close to the beach AND a short term rental opportunity on Longboat Key?! This is the one you've been looking for! You don't have to be a tennis player to understand the value of this fabulous townhome in Cedars Tennis Club. This 2 bedroom, 2 and a half bath condo is the perfect island escape. Beautifully updated and furnished, all you’ll need to bring is your bathing suit and a toothbrush to start enjoying island life to the fullest. Add to it a short term two week rental policy, this could also be your perfect investment property. Current annual income has been around $50,000, but that also includes a lot of family enjoyment in between. New impact windows, a new roof, 2021 air conditioning units and a private garage make this condo even more appealing. Spend your days in the sun with just a short walk to the beach or the Bay. Enjoy the community swimming pool, with a fabulous tiki bar. Join the club to enjoy the fitness center and tennis privileges. Take a bike ride on 11 miles of bike paths down the island or a walk to Joan Durante Park. The cultural mecca of downtown Sarasota is just a short drive away. And don’t forget to make time to see the stunning evening sunsets. The Longboat Key lifestyle is waiting for you!
6700 GULF OF MEXICO DR #139, LONGBOAT KEY, FL 34228
$449,000197 Days on yellowkey MLS ID: A4674675
REDUCED by $11,000 (2.4%) on 06/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1305 Built: 1969 Tax: $4,551 (2024)Community: Whitney BeachCondo
Taxes:$4,551
Remarks: “PRICED BELOW MARKET VALUE NOW REDUCED TO $449,000” 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. Second bedroom is very spacious & could be subdivided to include an office. Totally updated second bathroom has a 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)
842 BAYPORT WAY, LONGBOAT KEY, FL 34228
$625,00085 Days on yellowkey MLS ID: A4687058
REDUCED by $50,000 (7.4%) on 06/16/2026
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
Elementary School: Southside Elementary
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 comfortably furnished first floor corner residence gives the feeling of a private home with the ease of low maintenance living. A favorite feature of this property is the screened lanai that opens to a west facing extended brick patio. Perfect for easy mornings and catching brilliant sunsets. Step out the garden gate to landscaped grounds and a direct 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. Inside, The open layout includes a spacious kitchen, combined living and dining, a primary bedroom with office nook, ensuite bath with dual vanities and walk-in closet,second bedroom and full bath, plus the convenience of full sized in unit laundry, covered parking and private storage closet. There is also a brand new high efficiency HVAC system and a 2023 hot water heater. 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 among 27 acres of exquisitely landscaped tropical grounds,. 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 has rented off-season for several years and has everything one needs to start enjoying right away. 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 Agent: Rosemarie Mckee (941-504-9396)
2295 GULF OF MEXICO DR #54S, LONGBOAT KEY, FL 34228
$899,000117 Days on yellowkey MLS ID: A4683112
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $7,576 (2025)Community: Islander Club Of LongboatCondo
Taxes:$7,576
High School: Riverview High
Remarks: Welcome to The Islander Club — your turnkey getaway awaits! Step into coastal living with this beautifully updated residence offering effortless style and year-round relaxation. The open, sun-filled layout features tasteful luxury finishes and seamless access to a 38-foot terrace, perfect for unwinding after a day at the beach. Unit 54S has been thoughtfully upgraded throughout, showcasing wood flooring, an updated kitchen with stainless steel appliances, refreshed bathrooms, and unique architectural details that add character and charm. The sunlit primary bedroom includes an ensuite bathroom, a large walk-in closet, and a cozy seating area ideal for reading or enjoying your morning coffee. The spacious second bedroom welcomes guests with terrace access and a generous closet for added storage. The Islander Club’s resort-style amenities include a private 400' beachfront, heated pool, brand-new fitness center, two new sauna rooms, a Har-Tru™ tennis court, two pickleball courts and on-site management for true lock-and-leave convenience. The Islander Club has recently completed an extensive series of capital improvements that elevate both the structural integrity and the everyday experience of the community. Enhancements include exterior stucco repairs and balcony waterproofing, new roofs on the carports, clubhouse, and both residential towers, and modernized pool facilities with new resurfacing, tile, and equipment. Additional upgrades such as refreshed landscaping and lighting, hurricane-rated windows and doors, and a fully renovated fitness center further enhance the appeal and long-term value of the property. Whether you’re seeking a seasonal retreat or a full-time coastal home, this move-in-ready gem delivers the best of island living and peace of mind.
Listing Agent: Julie Lojacono Mackie (773-704-1438)
3806 GULF OF MEXICO DR #C209, LONGBOAT KEY, FL 34228
$335,00034 Days on yellowkey MLS ID: A4693850
2 Days Off yellowkey (back on 6/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1046 Built: 1970Monthly Fee: $1,346 Tax: $2,934 (2025)Community: Beach Harbor ClubCondo
Taxes:$2,934
Remarks: Under contract-accepting backup offers. Discover Your Slice of Paradise! This charming turnkey 2-bedroom, 2-bath condo is perfectly positioned between the Gulf of Mexico and Sarasota Bay, offering breathtaking sunrise and sunset views. Enjoy deeded beach access complete with lounge chairs, picnic tables, charcoal grills, and outdoor showers. On the bayside, recent upgrades include a new dock with first-come boat slips, community kayaks, an electric kayak launch, and a fishing pier with a cleaning station. Host a BBQ at the tiki hut or relax by the heated pool featuring gas grills, indoor restrooms, and an outdoor shower. The newly renovated clubhouse offers an upgraded fitness center, card room, large bar, full kitchen, and plenty of gathering space for entertaining.During season, this vibrant and friendly community comes alive with Wednesday night happy hours and festive celebrations including St. Patrick’s Day, Mardi Gras, Cinco de Mayo, and more.
Listing is courtesy of: FLORIDA GALLERY REAL ESTATE (941-315-6678)
Listing Agent: Kathleen Magnus (941-281-5539)
4350 CHATHAM DR #Unit E-208, LONGBOAT KEY, FL 34228
$640,000208 Days on yellowkey MLS ID: A4672221
REDUCED by $35,000 (5.2%) on 06/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1316 Built: 1969 Tax: $6,535 (2025)Community: Longboat HarbourCondo
Taxes:$6,535
Remarks: One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! REDUCED $35,000! NEWLY REMODELED • COASTAL LUXURY RESIDENCE Longboat Harbour • Building E #208 | Corner End Unit • Bay & Harbour Views. CLOSEST BUILDING TO A SHORT WALK ACCROSS THE STREET WITH A PRIVATE DEEDED GULF BEACH ACCESS WITH PAVILION, RESTROOMS AND SHOWERS TOTALLY REMODELED FROM FLOOR TO CEILING second-floor corner residence in the highly sought-after Longboat Harbour Community. This light-filled home captures sweeping views of Sarasota Bay and Longboat Harbour. This spacious two-bedroom, two-bath retreat has been transformed with exceptional attention to detail. Elevated finishes, a soothing coastal palette, and an airy open layout blend modern luxury with effortless livability. Corner units of this caliber are rarely available. From the two bedrooms, you step out to the exceptionally Large Lanai with floor to ceiling sliding glass doors. A SHOWCASE KITCHEN WITH TWO SUNLIT WINDOWS AND WATER VIEWS Elegant, functional, and beautifully appointed: • Frigidaire Professional stainless steel appliances • Gleaming quartz countertops • 9-inch deep sink • Pull-out cabinet shelving • Pantry closet • Designer tile backsplash • Large Eat-In Kitchen with water views & sunsets • Instant hot-water. LUXURIOUS PRIMARY SUITE An elevated retreat professionally designed for comfort and relaxation • Private ensuite bath • Custom California Closet walk-in wardrobe • Built-in desk feature • Remote-controlled luxury solar shades. RESORT-INSPIRED AMENITIES Longboat Harbour offers a lifestyle unmatched on the Gulf Coast: • Designated covered parking spot conveniently located • Personal storage space on the third floor • Private deeded Gulf beach access with pavilion, restrooms & shower • Four sparkling pools • Fitness center & sauna • Tennis & pickleball courts • Billiards room, library & meeting rooms • Picnic areas with grills • Putting green • Fishing pier • Affordable resident-only boat dockage • KAYAK LAUNCH and KAYAK WHICH SELLER WILL BE GIFTING TO THE BUYER. Enjoy effortless waterfront living and endless ways to explore the natural beauty of Longboat Key. PROPERTY ENHANCEMENTS & UPDATES: Thoughtfully improved for comfort, reliability, and peace of mind: • NO HURRICANE DAMAGE OR FLOODING • Bosch Washer & Dryer • Newer AC: 12/5/21 • Newer Hot Water Heater: 3/3/17 • New roofs throughout the community • Electrical and plumbing systems updated. A BEAUTIFULLY RENOVATED INTERIOR THAT CREATES THE ULTIMATE COASTAL LIFESTYLE/ THE MONTHLY HOA FEE INCLUDES HAZARD, HURRICANE AND FLOOD INSURANCE/ RESERVES HAVE BEEN FULLY FUNDED
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Billie Chipain (941-587-8556)
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,00089 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)
4234 GULF OF MEXICO DR #M1, LONGBOAT KEY, FL 34228
$649,0005 Days on yellowkey MLS ID: A4696419
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $2,383 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$2,383
Remarks: It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!
Listing Agent: John Thorson, Pa (941-914-1366)
1930 HARBOURSIDE DR #122, LONGBOAT KEY, FL 34228
$549,00050 Days on yellowkey MLS ID: A4692494
REDUCED by $10,000 (1.8%) on 06/19/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1192 Built: 1982 Tax: $6,584 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$6,584
Remarks: Welcome to your waterfront retreat in the highly sought-after Fairway Bay community, where relaxed coastal living meets thoughtful design and modern comfort. This beautifully renovated 2-bedroom, 2-bath condominium offers nearly 1,200 square feet of light-filled interior space, along with sweeping views of Sarasota Bay and the downtown skyline that create a stunning and ever-changing backdrop throughout the day. Fully updated in 2020 and professionally curated by an interior designer, the residence showcases a refined yet inviting aesthetic. Inside, the open-concept layout is enhanced by warm, driftwood-inspired luxury vinyl plank flooring and an abundance of natural light. The living and dining areas flow effortlessly together, while expansive pocketing sliders open wide to a private balcony, creating a seamless indoor-outdoor experience ideal for both quiet mornings and evening entertaining. From this vantage point, you can take in tranquil water views, coastal breezes, and vibrant sunsets that define the Longboat Key lifestyle. The galley-style kitchen is both stylish and functional, featuring quartz countertops, crisp Ivory soft-close cabinetry, New AC 2025, New Water Heater 2025, New Washer and Dryer 2025, stainless steel appliances installed in 2020, and a peninsula with seating that invites casual dining and conversation. The design balances clean lines with timeless finishes, making it equally suited for everyday living and hosting guests. The spacious primary suite serves as a private sanctuary, offering generous proportions, beautiful bay views, and direct access to the peaceful ambiance of the home. The en-suite bath is thoughtfully appointed with dual vanities, elegant lighting, and a walk-in tiled shower, creating a spa-like atmosphere. The guest bedroom and accompanying bath are equally well-designed, providing comfort and privacy for visitors while maintaining the home’s cohesive style. Additional features include plantation shutters on all windows and sliders, a private exterior entrance that enhances both convenience and privacy, a welcoming balcony seating area, and professionally landscaped surroundings that add to the property’s curb appeal. Important updates such as a new air conditioning system and water heater provide peace of mind, making this a truly move-in-ready opportunity. Fairway Bay, located within the desirable Bay Isles community, offers a lifestyle rich in amenities and natural beauty. Residents enjoy gated entry with 24-hour guard service, beautifully maintained grounds, resort-style pools, a clubhouse, fitness center, and tennis courts. Scenic walking and biking paths wind along the bay, while a kayak and paddleboard launch provides easy access to the water for outdoor enthusiasts. Ownership also includes exclusive access to a private beach club on the Gulf of Mexico, offering the rare advantage of experiencing both serene bayfront living and pristine Gulf beaches. Ideally situated near the renowned The St. Regis Longboat Key Resort, this residence is just moments from exceptional dining, shopping, and leisure experiences, further enhancing its appeal as both a full-time residence and seasonal escape. This is more than just a condominium—it is an opportunity to embrace the relaxed elegance, natural beauty, and effortless lifestyle that make Longboat Key one of Florida’s most coveted coastal destinations.
Listing Agent: David Leventhal (941-518-7694)
521 BAYPORT WAY #521, LONGBOAT KEY, FL 34228
$649,00010 Days on yellowkey MLS ID: TB8518960
0 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1980Monthly Fee: $1,978 Tax: $5,669 (2025)Community: Bayport Bch & Ten Ph ACondo
Taxes:$5,669
High School: Booker High
Remarks: Under contract-accepting backup offers. Discover the essence of coastal resort living at Bayport Beach & Tennis Club on Longboat Key, a beautifully landscaped 27-acre Gulf-to-Bay community where every day feels like a vacation and the timeless charm of island living unfolds amid tropical beauty and world-class amenities. Surrounded by mature vegetation and scenic walking trails, this exceptional property offers 1,200 feet of private deeded Gulf of Mexico beach access just across the street and Sarasota Bay at your doorstep, complete with a fishing pier and kayak launch for enjoying Florida's spectacular waterfront lifestyle. This residence offers comfortable, maintenance-free living with an open floor plan, a tastefully updated kitchen, inviting indoor-outdoor living spaces, a private lanai, impact-resistant windows and doors, private covered parking, a private mailbox, and a private storage room ideal for bicycles and beach gear. Whether enjoying morning coffee on the lanai, taking an evening stroll along the beach, or watching Longboat Key's world-renowned sunsets paint the sky steps from your door, every day feels like a retreat. Residents enjoy an impressive collection of resort-style amenities, including a heated Junior Olympic lap pool, four Har-Tru tennis courts, a fitness center, clubhouse and community room, bayside fishing pier, kayak launch and storage areas, and an active, welcoming social atmosphere. On-site management and meticulously maintained grounds further enhance the carefree island lifestyle. Ideally located on infamous Longboat Key, Bayport offers the perfect balance of tranquility and convenience, just moments from Publix, Ace Hardware, pickle ball facilities, waterfront dining, exceptional shopping, boating, golf, St. Armands Circle, the Ringling Museum, dog parks, and the cultural attractions of downtown Sarasota. More than simply a condominium, Bayport is an opportunity to embrace one of Florida's most desirable island lifestyles, and this residence represents an exceptional value and one of the most attractively priced opportunities within this highly sought-after community. Come experience why so many residents say that living at Bayport isn't just owning a home—it's embracing a year-round island resort lifestyle that others only experience on vacation.
Listing is courtesy of: PERSONAL REALTY ADVISERS (727-317-7653)
Listing Agent: Rob Coscia (239-770-2683)
100 SANDS POINT RD #225, LONGBOAT KEY, FL 34228
$899,00039 Days on yellowkey MLS ID: A4693834
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1492 Built: 1966 Tax: $3,929 (2025)Community: Sands PointCondo
Taxes:$3,929
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET with a New Price and Turn Key! Welcome to your slice of paradise, where coastal living reaches new heights of sophistication, and nestled inside the gates of the Longboat Key Club. This gorgeous 1492 sq. ft. water front residence underwent a total transformation in 2023, and the results are nothing short of spectacular. Step inside this bright second floor residence and discover a two bedroom and two baths, with a view that feels serene, luxurious, and unmistakably coastal. This condo comes with a view of the private marina tucked away in a quiet cove, where you can enjoy watching the dolphins at play. Towering palm trees frame the scene beautifully, with the curved waterfront drive adds a resort-style elegance to this one-of-a-kind property. This kitchen has a bright, modern, upscale feel with a clean coastal-inspired design. White shake-style cabinetry with sleek brushed nickel handles, extending all the way to the ceiling for extra storage. Exotic granite counters, matched with a sleek white Carrara marble back splash. Stainless steel appliances, and a deep undermount sink with a tall industrial-style spring faucet. The expansive great room steals the show, with a dramatic wall of windows, open concept and LVP flooring thru out. Both bathrooms feature quartz counter tops, tiled floors and walk in showers. HVAC 2020. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room with kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. With in walking distance to well renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Diane Smith (941-313-4957)
2525 GULF OF MEXICO DR #3D, LONGBOAT KEY, FL 34228
$1,650,00016 Days on yellowkey MLS ID: A4696213
1 Days Off yellowkey (back on 6/16/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1468 Built: 1972 Tax: $18,254 (2025)Community: Islands WestSpa: YesCondo
Taxes:$18,254
Remarks: Under contract-accepting backup offers. Professional Photo's coming soon. Wake up to breathtaking, direct panoramic views of the Gulf of Mexico from this stunning third-floor beachfront residence on Longboat Key. Perfectly positioned to capture endless turquoise waters and spectacular sunsets, this coastal retreat offers unobstructed Gulf views, creating a serene backdrop for everyday living. The completely updated condo features two bedrooms, two baths, a spacious great room, dining area, and a kitchen with a charming breakfast nook. Walls of impact glass flood the interior with natural light, while floor-to-ceiling windows in both bedrooms showcase the ever-changing beauty of the shoreline. A wraparound balcony provides the perfect setting to enjoy morning coffee, coastal breezes, and mesmerizing sunsets over the Gulf. Ideally located mid-island, this residence offers the perfect balance of tranquility and convenience. Bay Isles Shoppes is just across the street, offering Publix, CVS, banking, dining, the Longboat Key Tennis Center, and Bayfront Park. World-renowned St. Armands Circle is only four miles away, while downtown Sarasota's acclaimed dining, shopping, arts, and entertainment are within a short seven-mile drive. Residents of Islands West enjoy an exceptional Gulf-front lifestyle with an impressive collection of resort-style amenities. The 15-story community features secure key-fob entry, a heated beachfront pool and spa, outdoor grilling and lounge areas, tennis and pickleball courts, and dedicated storage for bicycles, kayaks, and paddleboards. The clubhouse is currently being transformed to include a stylish social room with library, state-of-the-art fitness center, and catering kitchen. Pet lovers will appreciate the welcoming two-pet policy. Experience the ultimate beachfront lifestyle where spectacular views, resort-inspired amenities, and an unbeatable Longboat Key location come together in one extraordinary residence.
Listing Agent: Midge Mccarthy (941-809-3800)
4234 GULF OF MEXICO DR #E2, LONGBOAT KEY, FL 34228
$580,000250 Days on yellowkey MLS ID: A4667654
REDUCED by $18,000 (3.0%) on 06/04/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1973 Tax: $10,617 (2025)Community: Pelican Harbour & Beach ClubCondo
Taxes:$10,617
Remarks: REDUCED AND INCREDIBLE VALUE! EXCEPTIONAL FULL BAY VIEWS, PRIVATE BEACH ACCESS AND KAYAK LAUNCH, HURRICANE-RATED WINDOWS AND SLIDERS, UPDATED BATHS AND MORE! This 2BR/2BA retreat at Pelican Harbour & Beach Club delivers the quintessential Longboat Key lifestyle. From its 2nd-floor vantage point, enjoy peaceful sunrises over the Bay and the tranquil fountain view from your screened lanai, surrounded by lush tropical landscaping. Then, end your day with spectacular Gulf sunsets and leisurely beach walks from your private beach access. The updated kitchen gleams with new 2025 solid quartz countertops, stainless Samsung appliances, a tile backsplash, and a breakfast bar island—perfect for entertaining. Open living and dining areas flow seamlessly toward the water, creating a bright, inviting space ideal for relaxing or hosting friends. The spacious owner’s suite opens to the lanai and features a 2023-renovated ensuite bath with stone countertops, dual sinks, porcelain tile flooring, a glass shower, and custom closets. The guest suite offers another beautifully updated bath and generous storage. Additional highlights in-unit laundry, 2023 roof, 2024 exterior paint, and a hurricane-rated carport conveniently located just outside your door. This unit is currently rented, and tenants will vacate or stay so you can continue to earn rental income immediately! Ideally situated mid-island, Pelican Harbour & Beach Club offers outstanding amenities: Bay and beach access, first-come dock slips, a heated resort-style pool, two newly resurfaced tennis/pickleball courts, a clubhouse with social activities, kayak storage and launch, bike storage, and ample owner storage. This pet-friendly, rental-friendly community welcomes large dogs and seasonal visitors and perfectly combines luxury, flexibility, and coastal charm—just minutes from Bayfront Park, the new St. Regis Resort, St. Armands Circle, and downtown Sarasota’s vibrant restaurants, culture, and shopping.
Listing Agent: Lenore Treiman (941-356-9642)
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