Location: Longboat Key
Do Not Show Listings
7115 GULF OF MEXICO DR #23, LONGBOAT KEY, FL 34228
$885,0001 Day on yellowkey MLS ID: A4699687
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1170 Built: 1974 Tax: $10,018 (2025)Community: LongbeachSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,018
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Never miss another beach day or a green flash sunset in this rarely available 2 bed 2 bath home in the Longbeach Community- a GULF FRONT enclave on the tip of Longboat Key. A short walk to the beach, thoughtfully remodeled and move-in ready, this residence offers spectacular daily views of the Gulf, pool, and lush tropical landscaping- best enjoyed on the 200 sqft screened terrace where there’s plenty of room for reading, relaxing or toasting the sunset and dining. This lovely residence has been loved and meticulously upgraded with superior materials and workmanship. The gourmet kitchen features a spacious central cooking island with Electrolux 6-burner cooktop and hood, brushed stainless GE Monogram and Bosch appliances including a stacked double oven, as well as granite countertops, and solid light cherry cabinets. A breakfast bar, wine rack and built-in office complement this kitchen with added functionality. Additional luxury finishes include raised ceilings, crown molding, hidden surround-sound speakers, and spa-inspired bathrooms with custom mosaic-tile showers, Kohler fixtures, and rain showerheads. The Longbeach Community offers 9.2 acres of Gulffront beach homes just a 5-min walk to the exclusive amenities like private beach access to the quartz-white sand of Longboat Key's beaches, a heated pool, private tennis, and ample parking. In addition to idyllic award-winning beaches, Longboat Key living means exquisite waterfront dining, boutique shopping in St Armands Circle, and unparalleled golf courses and tennis courts. The Longboat Key lifestyle awaits you to create new everlasting memories here in paradise!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
4500 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$769,000249 Days on yellowkey MLS ID: A4671822
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,913 (2025)Community: Windward Bay AmdCondo
Taxes:$7,913
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: "One Chance! One Corner-End Condo! One Dream! Don’t Let It Slip Away!” The only coveted South Marina corner/end unit currently on the market at Windward Bay—these special residences are truly prized. End units are usually the first to sell, and for good reason: they offer approximately 250 additional square feet of living space, flooding your home with light and delivering a bright, inviting atmosphere you’ll love. This second-floor location is equally exceptional—it’s the only level where you can enjoy continuous flooring throughout, creating a sleek and modern look. No one below means more freedom, more fun, and more style. Truly extraordinary, this special end unit offers a front-row seat to nature’s most enchanting show. Picture dolphins leaping in the sparkling waters and gentle manatees gliding just below your window—the very reason the current owners fell in love with this home. From breathtaking sunrises to moonlit reflections shimmering across Sarasota Bay, every moment feels like a postcard come to life. Step inside and feel the difference! Where luxury meets comfort with a complete remodel featuring a stunning Thomasville kitchen, sleek new floors, and beautifully updated bathrooms (2022). Enjoy modern conveniences like a Midea refrigerator, remote-control blinds (2025), and most importantly peace of mind with automatic hurricane shutters in the Living and Florida Rooms. This two-bedroom, two-bath property is more than a condo—it’s a lifestyle defined by serenity, security, spectacular views, and maintenance free living. Located in pet-friendly Windward Bay, where two pets are welcome, this community offers the best of Longboat Key Coastal Dream Living. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez fishing village, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. Windward Bay is a financially healthy Condo Association with a proactive Board. The Milestone Inspection and Capital Reserve Study are complete, Monthly Condo Fees for 2025 were actually reduced, and the new 2026 Monthly Condo fees only increased by $13. Own the best of Longboat Key Bayfront living and make it yours before it’s just a memory! Paradise has an address..and it's 4500 Gulf of Mexico Drive #G206 on Longboat Key, in the rare gem of a community known as Windward Bay! Contact us today to schedule your private showing. Live the Magic & Don't Miss Out! Your Waterfront Dream Awaits!”
Listing Agent: Debby Mccaig (941-544-1713)
4440 EXETER DR #301, LONGBOAT KEY, FL 34228
$535,000139 Days on yellowkey MLS ID: A4684917
4 Days Off yellowkey (back on 7/22/2026)
REDUCED by $5,000 (0.9%) on 07/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1970 Tax: $8,101 (2024)Community: Longboat HarbourCondo
Taxes:$8,101
Tax Year: 2024
Remarks: Motivated Seller, make an offer. Welcome to this beautifully updated top floor corner furnished residence with Gulf and Bay views that is move in ready. Coming furnished with an open kitchen floor plan and an enclosed lanai overlooking the pool and Sarasota Bay. Large plank ceramic tiles throughout and ceiling fans in every room, hurricane impact glass windows in the kitchen and living area and a washer/dryer has been added. All tv's within the residence stay. The Longboat Harbour community is located mid-Longboat Key with amenities to enjoy including a large clubhouse where many activities occur, with a catering kitchen and dance floor, art studio, billiard and card rooms, and a fully equipped fitness center. In addition, the community has four heated swimming pools, putting green, tennis and pickleball courts, kayak storage, boat slips available for a minimal annual fee for up to a 34’ boat, mini golf, a scenic waterfront promenade along the harbor and canal, and access to a private gated Beach Club on the Gulf side with bathrooms, showers and beach items. The building has just completed a new roof installed. There is additional storage withing the building for each residence as well as a storage closet on the enclosed lanai.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
210 SANDS POINT RD #2405, LONGBOAT KEY, FL 34228
$969,000320 Days on yellowkey MLS ID: A4664039
REDUCED by $131,000 (11.9%) on 07/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 650 Built: 1982 Tax: $9,827 (2024)Community: Inn On The Beach Ph ICondo
Taxes:$9,827
Remarks: Located behind the gates of the highly desirable Longboat Key Club, this 1BR/1BA Club Suite at Inn on the Beach offers a unique opportunity to own within the prestigious Longboat Key Club Resort. Spanning 650 sq. ft., this residence provides both convenience and privacy, with an expansive covered terrace offering peaceful Gulf views while keeping you close to every amenity. Completely renovated and meticulously styled, the interior pairs warm wood accents with neutral tones, complemented by faux wood tile floors flowing throughout. Dual sliders frame shimmering Gulf waters and invite natural light into the living space. The kitchen is a standout, with stone countertops, harmonizing cabinetry with glass panel accents and a colorful tile backsplash that adds just the right touch of vibrancy. Off the bedroom space, a beautifully updated bath features all-white cabinetry, a separate water closet and a glass walk-in shower with striking tilework. For added ease, in-unit laundry utilities are included. This unit participates in the Resort Rental Program and has a healthy rental history, with nightly rentals allowed, making it both an enjoyable retreat and a strong investment. As an owner, you’ll have access to the exclusive amenities of the 410-acre Longboat Key Club, including 45 holes of championship golf, 20 Har-Tru tennis courts at the award-winning Tennis Gardens, a full-service marina, private Gulf-front beach with umbrellas and attendant service, a world-class fitness and wellness center, spa and five private dining options. Recently renovated guest services, dining areas, and resort amenities have elevated the experience even further, earning accolades such as the AAA Four-Diamond Award and recognition from Condé Nast Traveler as a Top Florida Resort.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Bruce Myer (941-376-5311)
415 L AMBIANCE DR #A301, LONGBOAT KEY, FL 34228
$6,100,000110 Days on yellowkey MLS ID: A4688759
2 Days Off yellowkey (back on 7/22/2026)
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3380 Built: 1992 Tax: $46,418 (2025)Community: L Ambiance 1Spa: YesCondo
Taxes:$46,418
Remarks: Under contract-accepting backup offers. Rare corner Gulf-front residence with expansive wraparound terrace and views. An exceptional residence in L’Ambiance, where sweeping water views and refined coastal design converge. This light-filled corner home is defined by an expansive wraparound terrace, offering multiple seating areas and uninterrupted vistas of the Gulf - creating a seamless connection between indoor and outdoor living. Walls of glass frame the horizon from the main living spaces, enhanced by high-impact glass throughout, where generous scale and an open layout provide an effortless setting for both intimate living and entertaining. The kitchen is thoughtfully designed with extensive custom cabinetry, stone surfaces, and a functional layout complemented by a dedicated dining area. A private split-bedroom plan enhances comfort and separation, while a flexible den or media room offers additional space for guests or a home office. Throughout the residence, polished flooring and plantation shutters add a layer of understated sophistication. This residence includes two garage parking spaces, a private wine locker, and additional storage, offering both convenience and security. L’Ambiance offers a boutique beachfront setting with concierge service, a well-appointed fitness center, three guest suites for visiting family and friends, two Har-Tru tennis courts, and an expansive resort-style pool and spa set within beautifully maintained tropical grounds, all with direct beach access. Ideally positioned on the south end of Longboat Key and adjacent to the Longboat Key Club, with optional membership offering access to championship golf, tennis, marina, dining, and a full-service spa, this is a rare opportunity to experience elevated beachfront living.
450 GULF OF MEXICO DR #B207, LONGBOAT KEY, FL 34228
$650,000291 Days on yellowkey MLS ID: A4667364
0 Days Off yellowkey (back on 7/21/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1474 Built: 1970 Tax: $6,830 (2024)Community: Bay Harbour AptsCondo
Taxes:$6,830
Remarks: Under contract-accepting backup offers. Where can you find an exquisite 3-bedroom waterfront condo on the coveted South End of Longboat Key under $700,000? Discover the ultimate island lifestyle in this beautifully furnished end unit located in the highly sought-after Bay Harbour community. Boasting a desired southern exposure, lower maintenance fees, and a pet-friendly policy, this condo is the perfect blend of comfort and convenience. Even better, the 2023 special assessment of $23,000 has been paid in full, covering a new roof, total building painting, and internal pipe lining. This immaculate home features a bright, coastal interior with a serene, open layout and spectacular bay and pool views through the multiple windows only an end unit can offer. The living room and third bedroom are elevated by beautiful moldings and updated ceilings, while the newer kitchen is a chef’s dream with all under-cabinet pull-out drawers and a clever corner turn-around for maximum storage. The bathrooms present an excellent opportunity for a new owner to customize and enhance the space with contemporary finishes. The primary suite is a true retreat, offering breathtaking water views and exceptional closet space with his-and-her built-ins. A unique design feature allows the hallway door to close, transforming the master entry into a private dressing room complete with a full-length mirror. For guests, the hallway is equipped with a pocket door to provide more privacy. The master bedroom also is equipped with a pocket door. Whether you use the expansive third bedroom for visiting family or as a home office, the versatility of the space is unmatched. Step outside and immerse yourself in the beauty of Sarasota Bay, where you'll enjoy direct access to a kayak launch and optional boat slips just steps from your front door. For boating and nature enthusiasts, Bay Harbour is a true gem. Enjoy direct access to a kayak launch and optional boat slips just steps from your front door. With no bridges to Sarasota Bay and just one to the Gulf, you'll have unrestricted access to deep waters for boats up to 42 feet. The remodeled marina is fully equipped with electrical, freshwater, and a fish cleaning station, while the seawall offers frequent visits from dolphins and playful manatees. This unparalleled location is just minutes from world-renowned St. Armands Circle and downtown Sarasota, and it is walkable to the Longboat Key Club, Dry Dock, and Charthouse. Whether you're seeking a permanent residence or a seasonal retreat, this waterfront oasis offers the perfect combination of location, luxury, and lifestyle.
Listing Agent: Mairead Smialek (847-334-4848)
1915 HARBOUR LINKS CIR #6, LONGBOAT KEY, FL 34228
$1,950,000111 Days on yellowkey MLS ID: A4688148
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2476 Built: 2002 Tax: $19,319 (2025)Community: Bay IslesSpa: YesCondo
Taxes:$19,319
Elementary School: Southside Elementary
High School: Sarasota High
Middle School: Booker Middle
Remarks: Now Offered Fully Furnished & Turnkey! Welcome to effortless coastal living in Harbour Links at Bay Isles, a gated, maintenance-free community on beautiful Longboat Key. This move-in-ready villa is being sold fully furnished and turnkey, making it the perfect primary residence, seasonal home, second home, vacation retreat, or lock-and-leave Florida getaway. Designed for comfortable everyday living and entertaining, the light-filled floor plan features soaring ceilings, spacious living and dining areas, a well-appointed kitchen, and a private screened lanai—ideal for enjoying Florida's year-round sunshine. The generous primary suite located on the first floor offers a peaceful retreat with an en-suite bath and abundant closet space, while the guest accommodations provide comfort and privacy for family and friends. Private Bay Isles Beach Club, offering deeded access to the sandy beaches and turquoise waters of the Gulf of Mexico. Optional membership to the Longboat Key Club provides championship golf, tennis, pickleball, fitness facilities, marinas, waterfront dining, and an active social calendar. Perfectly located just minutes from St. Armands Circle, downtown Sarasota, waterfront restaurants, boutique shopping, marinas, boating, cultural attractions, and world-renowned Gulf Coast beaches, this exceptional property offers the best of Florida coastal living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Cathy Palmer (678-524-1104)
605 SUTTON PL #201, LONGBOAT KEY, FL 34228
$619,000117 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)
4420 EXETER DR #303, LONGBOAT KEY, FL 34228
$550,000177 Days on yellowkey MLS ID: TB8455704
REDUCED by $25,000 (4.3%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970Monthly Fee: $1,412 Tax: $3,678 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$3,678
Remarks: Enjoy tranquil, unobstructed Sarasota Bay views from this top-floor, two-bedroom, two-bath partially furnished residence in the desirable Longboat Harbour community. Fresh paint and updated lighting in some areas of the home enhance the bright, inviting interior, while comfortable living spaces offer peaceful water views from most rooms. The kitchen features stainless steel appliances, the hall bath has been refreshed with timeless finishes, and impact windows plus in-unit washer and dryer hookup add everyday convenience. Longboat Harbour offers resort-style amenities including multiple heated pools, fitness center with sauna, tennis, pickleball, shuffleboard, fishing pier, boating docks up to 34 feet, bike and kayak storage, on-site management, and deeded beach access just across the street with gated parking and facilities. Perfectly located mid-key for relaxed island living.
Listing is courtesy of: SMITH & ASSOCIATES REAL ESTATE (727-342-3800)
Listing Agent: Jerry Gemmecke (317-445-2434)
4725 GULF OF MEXICO DR #314, LONGBOAT KEY, FL 34228
$724,900228 Days on yellowkey MLS ID: A4673798
REDUCED by $25,000 (3.3%) on 06/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1104 Built: 1974 Tax: $10,125 (2024)Community: Sand CayCondo
Taxes:$10,125
Remarks: Welcome to Sand Cay Beach Resort—one of Longboat Key’s premier vacation destinations. VACATION WHEN YOU WANT - GENERATE INCOME WHEN YOU DON'T - TURNKEY GULF-SIDE INVESTMENT WITH REAL RETURNS. Rarely available third-floor condo truly impresses with soaring vaulted ceilings exclusive to top-floor residences, a beautifully updated kitchen, and tasteful coastal-inspired finishes throughout. A well-established vacation rental with a strong income history, this property is an ideal opportunity for both personal enjoyment and investment. Nestled within an intimate beachfront community offering 340 feet of pristine Gulf frontage, Sand Cay provides an exceptional resort-style experience. Residents and guests enjoy first-class amenities including tennis courts, shuffleboard, a heated pool, basketball area, barbecue stations, a full-time on-site manager, and a convenient in-house rental program. Perfectly located, the resort is just minutes from the boutique shops and fine dining of St. Armands Circle and the vibrant arts and cultural attractions of downtown Sarasota. Light and bright, this third-floor garden-view condo is ideally situated between the pool and the beach. The inviting floor plan features two bedrooms, two bathrooms, a spacious living and dining area, an updated and fully equipped kitchen, a cozy den/office nook, and a private balcony with an awning—ideal for morning coffee or unwinding after a day by the Gulf. Your slice of Longboat Key paradise awaits. Schedule your showing today.
Listing Agent: Michael Albano, Pa (941-993-9571)
836 EVERGREEN WAY, LONGBOAT KEY, FL 34228
$975,000222 Days on yellowkey MLS ID: A4674750
REDUCED by $20,000 (2.0%) on 06/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2813 Built: 1991Monthly Fee: $1,644 Tax: $4,852 (2025)Community: Cedars East Sec 3Condo
Taxes:$4,852
Remarks: Investor Dream Home! A double condo unit which feels like a single-family home, because it is not attached to anything but sunshine, the bay and dreams! Elevated among the treetops on the bay side of Longboat Key, it features 2 oversized garage spaces, wood floors throughout the first elevated living level, an open great room and kitchen for entertaining, an inviting wood-burning fireplace, screened lanai for bay breezes and a flex room to use as an office, den or guest room. Upstairs you will find 2 bedrooms which share a full bath and a primary bedroom with a view of Sarasota Bay through a wall of windows and a screened lanai where you can catch the sunset glow over the treetops. The ensuite primary bath features dual sinks and 2 large walk-in closets. Amenities in the premier tennis community include exceptional access to bay waters, perfect for launching a kayak, fishing and enjoying the tide pools. Enjoy a boardwalk stroll through mangroves and watch the sunrise from a private bayside dock (no boat access). Pool membership comes with home ownership. Tennis, pickleball and fitness center access is available through Cedars East Resort at an annual rate. Update, redesign and make it your home or income opportunity today!
Listing Agent: Eileen Saunders (662-404-0816)
600 SUTTON PL #B302, LONGBOAT KEY, FL 34228
$449,00096 Days on yellowkey MLS ID: A4690036
REDUCED by $26,000 (5.5%) on 07/21/2026
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
Middle School: W.D. Sugg Middle
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)
4390 EXETER DR #107, LONGBOAT KEY, FL 34228
$425,0002 Days on yellowkey MLS ID: A4700306
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970Monthly Fee: $1,412 Tax: $6,381 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,381
Remarks: Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Sharon Meier (407-927-5669)
5757 GULF OF MEXICO DR #205, LONGBOAT KEY, FL 34228
$895,0007 Days on yellowkey MLS ID: A4699882
0 Days Off yellowkey (back on 7/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1561 Built: 1973Monthly Fee: $1,576 Tax: $6,432 (2025)Community: The ShoreCondo
Taxes:$6,432
Remarks: Experience the perfect blend of luxury, comfort, and effortless beachfront living at The Shore Condominiums on prestigious Longboat Key. This beautifully renovated residence offers two spacious bedrooms, two elegantly updated bathrooms, plus a private office. This is your own personal beach retreat - an ideal design for entertaining family and friends, working remotely, or simply enjoying the quiet beaches of the Key. Thoughtfully redesigned with exceptional craftsmanship, the home features a chef-inspired kitchen with custom cabinetry, premium finishes, and an open, inviting floor plan perfect for entertaining. Recent upgrades include hurricane-impact windows and doors, a high-efficiency air conditioning system, tankless water heater, crown molding, porcelain flooring, plantation shutters, and an in-unit laundry room complete with washer and dryer. The spacious primary suite offers floor-to-ceiling Gulf views, custom bath, and large walk-in closet. The large guest suite, split from the primary, offers friends and family privacy, as well as an adjoining custom bath. A separate private storage room provides ample space for beach equipment, bicycles, and seasonal belongings. Enjoy breathtaking Gulf views, spectacular year-round sunsets, and the soothing sounds of the surf from your own beachfront sanctuary. Just steps from your door, the pristine private beach invites morning walks, shelling, swimming, and unforgettable evenings watching the sun disappear into the Gulf. The Shore is a Pet-Friendly community, beautifully maintained, known for its lush tropical landscaping, and relaxed coastal atmosphere. Residents enjoy exceptional amenities, including a heated beachfront pool, well-equipped fitness center, and a spacious clubhouse with a caterer's kitchen for social gatherings and private events. Equally impressive, the association is professionally managed, meticulously maintained, and boasts fully funded reserves, providing owners with confidence in the community's long-term financial health and stewardship. Perfectly located on the coveted shores of Longboat Key, this move-in-ready residence offers an exceptional opportunity to embrace an elegant yet casual beachfront lifestyle where every day feels like a vacation.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Michael Seamon (941-586-1802)
1591 GULF OF MEXICO DR #216, LONGBOAT KEY, FL 34228
$2,750,000307 Days on yellowkey MLS ID: A4665247
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1556 Built: 2025 Tax: $25,560 (2025)Community: St. Regis Longboat KeySpa: NoCondo
Taxes:$25,560
Remarks: Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lynn Morris, Pllc (941-400-4526)
350 GULF OF MEXICO DR #213, LONGBOAT KEY, FL 34228
$899,50040 Days on yellowkey MLS ID: A4696547
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2378 Built: 1992 Tax: $13,172 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$13,172
High School: Booker High
Remarks: Welcome to one of Longboat Key's premier bayfront communities, Tangerine Bay Club, where your days are spent like you live at a luxury resort! This three bedroom, 2 and a half bath elevated residence offers spacious living with gorgeous views of the mote style lagoon, spectacular resort style pool and Sarasota Bay. A private 2 car garage only adds to the many benefits of living here. Did we mention the day dock and pier over Sarasota Bay? The community gym overlooking the gorgeous pool? The Tennis and pickleball courts? The ability to purchase a membership at the Bay Isles Beach club for only a nominal yearly fee? This is truly island living at its best! A welcoming front entrance courtyard allows for a wonderful arrival spot just steps from the elevator yet this unit, being a corner residence, feels very private. Once inside you'll be immediately impressed with the light filled spaces that allow for you to enjoy the incredible views from multiple large windows. A balcony accessed from the great room and the Primary bedroom is a spot you'll want to enjoy every morning with your coffee and every evening with your cold beverage. Just a short distance from multiple restaurants, the Longboat Key Club, The St.Regis resort and the bridge that takes you over to St.Armands Circle and then onto the cultural mecca of downtown Sarasota....at a price that makes it easy to imagine. Whether you choose to renovate and make it your own or enjoy it just as it is, this is one you will want to see!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$499,000201 Days on yellowkey MLS ID: A4676730
REDUCED by $46,000 (8.4%) on 06/15/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
2850 GULF OF MEXICO DR #5, LONGBOAT KEY, FL 34228
$324,00084 Days on yellowkey MLS ID: A4691701
REDUCED by $24,000 (6.9%) on 07/16/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 657 Built: 1967 Tax: $4,601 (2025)Community: Neptune On Longboat KeySpa: NoCondo
Taxes:$4,601
Remarks: A renovated condo directly across from public beach access under $350,000. on Longboat Key? This is the one you've been looking for! Perfectly positioned for both personal enjoyment and strong rental income potential. Whether you're seeking a low-maintenance vacation escape or an income-generating property, this location checks all the boxes. Walk across the street to watch sunset on the sand, then stroll to Publix, Bayfront Park's tennis & pickleball courts, the library, or one of the island’s cozy dining spots. Everything your guests—or you—could want is right at your doorstep. The unit features a bright, open living space with tile flooring, a spacious bedroom, walk-in closet and parking. The well-maintained community offers low HOA fees and a relaxing island vibe that keeps guests coming back. Don’t miss out on this rare opportunity to own on Longboat Key—whether you're investing in your future or your lifestyle.
554 SPANISH DR S, LONGBOAT KEY, FL 34228
$405,000111 Days on yellowkey MLS ID: A4688632
REDUCED by $30,000 (6.9%) on 07/20/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1326 Built: 1971 Tax: $2,179 (2025)Community: Spanish Main Yacht Club CondoCondo
Taxes:$2,179
Remarks: Virtually Staged. Welcome to Spanish Main Yacht Club waterfront community and your new home! Light and bright, this stand-alone villa is all new and beautifully updated in 2026. White marble-like large porcelain tile floors that span the entire living area, providing a continuous flow throughout the villa. The new kitchen boasts stainless steel appliances, white quartz countertops, new cabinetry, lighting and more. Attractive updates in the primary en suite bedroom and guest bath as well. A nice added feature is the spacious interior laundry room. Beautiful, lush backyard view with privacy and an extra brick paver side yard and outdoor space. A short stroll to the privately deeded beach entrance to gorgeous Gulf beaches. Two minutes to have your toes in the soft, pearly sand. This is a boater’s paradise with slips available for an extremely inexpensive lease and direct access to Sarasota Bay, the Intracoastal waterway and azure waters of the Gulf. Only a short drive to the fantastic shops, restaurants and cultural events Sarasota and St. Armands Circle have to offer. This is a great investment opportunity and chance to enjoy Longboat Key living. The community is in the build-back stage due to damage from hurricanes in 2024 and is almost complete. All 212 units in Spanish Main are under FEMA requirements, guidelines, and stringent adherence to rebuild specifications and inspections from Town of Longboat Key. This is an opportunity to continue to make this villa your custom home.
Listing Agent: Kimberly Freiwald (941-256-6775)
2301 GULF OF MEXICO DR #12N, LONGBOAT KEY, FL 34228
$1,225,27749 Days on yellowkey MLS ID: A4695851
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1235 Built: 1970 Tax: $9,496 (2025)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$9,496
Remarks: A rare opportunity to own a beautifully reimagined Gulf-front residence at the prestigious Islander Club on South Longboat Key. Completely renovated with sophisticated coastal elegance, this exceptional beachfront condominium offers the convenience of first-floor walk-out living with direct access to the resort-style beachfront pool and the pristine white sands of the Gulf of Mexico. Walls of glass frame breathtaking panoramic Gulf views while filling the residence with natural light and spectacular sunsets. Thoughtfully redesigned with high-end finishes, the residence features a luxurious open-concept floor plan, a stunning chef's kitchen, beautifully appointed baths, and seamless indoor-outdoor living. The private beachfront terrace serves as an extension of the living space, creating the perfect setting for morning coffee, sunset cocktails, and effortless entertaining. Ideally positioned on the coveted south end of Longboat Key, this residence offers the privacy and comfort of a beachfront home with the convenience of luxury condominium living. Residents enjoy an impressive collection of amenities including 400 feet of private beachfront, an Olympic-size beachfront pool, a newly renovated fitness and community center, Har-Tru tennis courts with planned pickleball additions, on-site management, gated entry, and a highly desirable owner-to-owner rental program. Located just minutes from St. Armands Circle and vibrant downtown Sarasota, this exceptional residence places world-class dining, boutique shopping, cultural attractions, and marina amenities within easy reach. An extraordinary opportunity to experience refined Gulf-front living at one of Longboat Key's most sought-after beachfront addresses.
Listing Agent: Leah George (941-780-0597)
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