Location: Longboat Key
Do Not Show Listings
842 BAYPORT WAY #842, LONGBOAT KEY, FL 34228
$675,00026 Days on yellowkey MLS ID: A4687058
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1983 Tax: $5,662 (2025)Community: Bayport Bch & Ten Ph FSpa: NoCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,662
Elementary School: Southside Elementary
High School: None
Tax Year: 2025
Middle School: Booker Middle
Remarks: Poised within the Gulf to Bay community of Bayport Beach and Tennis Club, 842 Bayport Way offers 1570 square feet of effortless indoor-outdoor living. This first floor corner residence brings added natural light and extra privacy, giving the feeling of a private home with the ease of low maintenance living. The open layout includes a spacious kitchen, a primary bedroom with office space, walk-in closet and ensuite bath with dual vanities, as well as convenient in-unit laundry, covered parking and private storage closet. A combined dining and living area opens to a screened lanai and extended brick patio. This is a favorite spot for morning coffee, afternoon siestas and al fresco dining watching sunset skies. A garden gate leads to a direct side path to deeded beach access across the road. For pet owners, Bayport is small-pet friendly, and this walk-out location makes dog-walking especially easy. Spanning 27 acres of exquisitely landscaped tropical grounds, Bayport is celebrated for its timeless Tim Seibert architecture, exceptional amenities, and easy resort lifestyle. Residents enjoy a heated Jr. Olympic pool, clubhouse, fitness center, tennis, bocce ball, and shelled walking paths. Along the bay shoreline, a fishing pier, kayak launch and storage is perfect for morning paddles or simply enjoying nature . On the Gulf side, 1,200 feet of deeded beach access, complete with loungers and umbrellas, makes enjoying Longboat Key’s famously uncrowded beaches effortless. The condo’s split floor plan works well for year round living or a seaside escape. A favorable rental policy offers excellent income opportunity. Located mid-key, Bayport keeps you close to shopping, daily conveniences, great island dining, and the vibrance of Sarasota, all while feeling tucked away and serene. Settle in and enjoy a slice of true paradise on Longboat Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rosemarie Mckee (941-504-9396)
230 SANDS POINT RD #3703, LONGBOAT KEY, FL 34228
$1,875,00027 Days on yellowkey MLS ID: A4687684
0 Days Off yellowkey (back on 3/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1394 Built: 1982 Tax: $21,015 (2025)Community: Inn On The Beach Ph ICondo
Taxes:$21,015
Elementary School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Rarely available renovated corner two bedroom at The Resort at Longboat Key Club. Full gulf views from this 7th floor vantage are enjoyed from every room and the corner position offers extra square footage with extra windows. Located behind the gates of the Longboat Key Club, owners will enjoy the coastal contemporary finishes and excellent income history. As an owner, 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/wellness center, white sand beach with umbrellas and 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 the Longboat Life today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Ian Addy, Pa (941-961-8850)
4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228
$530,000111 Days on yellowkey MLS ID: A4676925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $6,041 (2024)Community: Longboat HarbourCondo
Taxes:$6,041
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: Located in the gated waterfront community of Longboat Harbour, this updated first floor residence offers direct walkout access to manicured green space and peaceful water views. Positioned near deeded beach access, the home provides a seamless blend of coastal living and everyday convenience. Interior features include tile flooring throughout, Frigidaire appliances, plantation shutters and automated blinds. The residence is offered turnkey furnished, including a West Elm leather sofa, coordinated coastal accent tables, coffee table, breakfast set and dining table with six chairs. The air conditioning system was replaced approximately two and a half years ago. All appliances and the hot water heater are under warranty, including parts and labor, through February 2027. Covered assigned parking and ample guest parking are included. Longboat Harbour is home to the Longboat Yacht Club, offering an active social calendar and waterfront gatherings for residents, whether or not they maintain a slip. Dock slips are available on a first-come basis for $460 per year. Community amenities include kayak storage and launch, seasonal dock rentals, a fitness center with instructor-led classes, tennis and pickleball courts, sauna, craft room, woodshop, library, and game rooms. No pets permitted. Rentals allowed twice annually with a 30 day minimum.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Sharon Meier (407-927-5669)
4370 CHATHAM DR #104, LONGBOAT KEY, FL 34228
$470,000142 Days on yellowkey MLS ID: A4674307
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $5,334 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$5,334
Remarks: Turnkey two-bedroom, two-bath residence in a first-floor, walkout location. Freshly painted with updated baths and 1,172 square feet of living space. Enjoy direct access to the harbor-front walking path and deeded beach access with baths, outdoor shower and chair storage. Includes a covered, assigned parking space. Resort-style amenities include a renovated clubhouse with kitchen and presentation space, fitness center, sauna, pickleball and tennis courts, outdoor grilling and entertainment area, kayak and paddleboard launch with storage, billiards, poker room, woodworking shop, library and bike storage. This self-managed community has strong reserves, no special assessments and no water intrusion from the 2024 storm season. Ideally located near Bayfront Park and just minutes from Publix, Longboat Key Town Center and St. Armands Circle.
225 SANDS POINT RD #6103, LONGBOAT KEY, FL 34228
$539,900290 Days on yellowkey MLS ID: A4658152
REDUCED by $29,100 (5.1%) on 04/24/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 642 Built: 1983 Tax: $6,997 (2025)Community: Inn On The Beach Ph IiiCondo
Taxes:$6,997
Remarks: Ideal for area residents needing space for overflow guests, or for out-of-state owners who want unlimited use with the ability to still earn income! The most perfectly peaceful lagoon views are enjoyed from this first floor Junior Suite in Building 6. Unlike the other buildings, this building boasts 10' ceilings making it feel especially spacious while optimizing natural light and view. It is typical to see manatees, dolphins, paddleboarders and a variety of tropical birds from the terrace overlooking the turquoise lagoon water. Building 6 offers extra privacy as it is located across the street from the main entrance, but still close enough to enjoy the pool and beach without having to pack the car and drive anywhere. Updates to the residence include new washer/dryer, new dishwasher, new microwave, new glass shower doors, new commode, new closet shelving, and new fire alarm. This unit is not part of the hotel program; however, it can be rented out by the owner or a 3rd party vendor on a nightly basis. Owners can also become members of the Longboat Key Club to partake in the numerous Resort amenities (Golf, Tennis, Restaurants, Fitness Center, Marina) if they still want to enjoy the benefits of owning in a Resort community without being part of the hotel program.
4400 EXETER DR #305, LONGBOAT KEY, FL 34228
$324,9003 Days on yellowkey MLS ID: A4691085
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 837 Built: 1970 Tax: $2,819 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$2,819
Remarks: Welcome to coastal living on coveted Longboat Key. Priced to move, this beautifully maintained 1-bedroom residence at 4400 Exeter Dr Unit 305J offers an exceptional opportunity to own in one of the island’s most desirable waterfront communities. Inside, you’ll find a bright open floor plan with warm wood flooring, an updated kitchen featuring stone countertops, stainless appliances, breakfast bar seating, and abundant custom storage. The spacious living area flows seamlessly to the enclosed lanai where tranquil water and tropical garden views create the perfect setting for morning coffee or evening relaxation. The generous primary suite includes large windows, great natural light, and access to a beautifully updated bath with dual vanities and modern finishes. Enjoy resort-style amenities including waterfront grounds, boat docks, pool, lush landscaping, and close proximity to deeded beach access, golf, tennis, dining, and shopping. Whether you’re seeking a seasonal retreat, investment property, or year-round island lifestyle, this value-priced Longboat Key residence is ready for immediate enjoyment. Opportunities at this price on Longboat Key do not last. Schedule your private showing today.
Listing is courtesy of: SVN COMMERCIAL ADVISORY GROUP (941-387-1200)
Listing Agent: Larry Starr (941-914-6869)
6700 GULF OF MEXICO DR #121, LONGBOAT KEY, FL 34228
$435,0004 Days on yellowkey MLS ID: TB8500916
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 936 Built: 1969 Tax: $5,653 (2025)Community: Whitney BeachCondo
Taxes:$5,653
Remarks: Best elevated water view in complex …fully renovated with mid-century classic furniture…a must see tranquil spot to see dolphin and manatee. Uncrowded beautiful beach …pool…walk to 3 great restaurants.
Listing is courtesy of: LISTED SIMPLY (800-995-5879)
Listing Agent: Sinan Zakaria (800-995-5879)
2165 GULF OF MEXICO DR #115, LONGBOAT KEY, FL 34228
$2,350,00057 Days on yellowkey MLS ID: A4684194
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2485 Built: 1996 Tax: $12,382 (2025)Community: Villa Di Lancia Ph 1Condo
Taxes:$12,382
High School: Booker High
Remarks: Experience and enjoy breathtaking, unobstructed Gulf views from this exceptional “walk-down” corner 3-bedroom 3-bath residence in the prestigious Villa Di Lancia community on South Longboat Key. Fully updated and spanning 2,485 sq. ft., this residence feels like its own private beachfront home. Upon entering from the semi-private elevator lobby, you are welcomed into an open and light-filled floor plan with soaring 10-foot ceilings and expansive walls of glass. As one of the most desirable corner residences in the community, this residence showcases panoramic Gulf views from nearly every room, which can be enjoyed by an additional wall of windows that flood the interior with natural light. The expansive great room connects to a nearly 500 sq. ft. covered terrace — your front-row seat to spectacular sunsets over turquoise waters! The terrace also has a private staircase allowing direct access to the beach and Gulf-front pool and spa, creating a rare and seamless indoor-outdoor lifestyle. The updated eat-in kitchen features a serving bar, walk-in pantry, full laundry room, and generous storage. The split floor plan allows owners and guests alike to enjoy quiet privacy. The primary suite is a true retreat, complete with direct Gulf views, private terrace access, spacious closets, and a large en-suite bath. The guest wing includes a second en-suite bedroom, as well as a third bedroom or a convenient and flexible den space with an adjacent bath. Villa Di Lancia is an exclusive boutique community with only 38 residences with resort-style amenities. Relax by the heated Gulf-front pool and spa, or enjoy friendly competition on the Har-Tru tennis and pickleball courts, as well as a state-of-the-art fitness center and steam room. Resort-style living has been effortlessly achieved throughout the community, including the newly updated clubhouse, social room and kitchen, on-site management, 24-hour manned gate, EV charging station, secure under-building parking, guest parking, and a private storage room. This welcoming community is both pet-friendly and impeccably maintained. Ideally located on the southern end of Longboat Key, residents enjoy proximity to fine and casual dining, golf, marinas, shopping, St. Armands Circle, and Sarasota’s cultural attractions. Residences here are rarely available. This is a rare opportunity to own a luxurious beachfront sanctuary and experience refined coastal living at its finest. This residence feels like a beautiful private home on the beach!
Listing Agent: Judy Kepecz-Hays (941-587-1700)
4325 GULF OF MEXICO DR #305, LONGBOAT KEY, FL 34228
$999,0004 Days on yellowkey MLS ID: A4690883
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1336 Built: 1975 Tax: $11,669 (2025)Community: Tiffany PlazaCondo
Taxes:$11,669
Remarks: Direct beachfront living! This beautifully updated 2-bedroom, 2-bath residence offers unobstructed Gulf of Mexico views and front-row access to a slice of Longboat Key’s most quiet and uncrowded shoreline. Available fully furnished and turnkey, this condo is ready for immediate enjoyment as a primary residence, seasonal escape, or investment property. The spacious open layout connects the kitchen, dining, and living areas, creating a bright and functional space designed to maximize natural light and water views. The private balcony is the perfect place to spot dolphins, manatees and other wildlife while enjoying morning coffee or evening sunsets. With only 42 residences, Tiffany Plaza offers a more private and welcoming atmosphere than larger condominium communities, with an active clubhouse and strong sense of community among owners. Residents also enjoy close proximity to Bayfront Park, featuring dog parks, tennis, pickleball, kayak facilities, fitness classes, and beautiful bay front walking paths.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Daniel Goldman (516-761-1911)
605 SUTTON PL #102, LONGBOAT KEY, FL 34228
$485,00080 Days on yellowkey MLS ID: A4681310
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 992 Built: 1973Monthly Fee: $1,642 Tax: $6,934 (2024)Community: Sutton PlaceCondo
Taxes:$6,934
Remarks: Sutton Place is perfectly situated on the tropical grounds of the Longboat Harbour Community. The two-bedroom, two-bathroom unit features beautiful views of the Sarasota Bay, spacious living area, full-size kitchen with stainless steel appliances and granite countertops, dining area and 3 flat-screen TV’s. If the amenities on the interior of the condo aren’t enough – the community of Sutton Place boasts two heated swimming pools, fishing pier and game room, complete with billiards and ping-pong; along with a fitness center and clubhouse. Deeded beach access is located directly across the street.
2425 GULF OF MEXICO DR #10F, LONGBOAT KEY, FL 34228
$1,495,000293 Days on yellowkey MLS ID: A4656887
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1513 Built: 1973 Tax: $14,482 (2024)Community: Sea Gate ClubSpa: NoCondo
Taxes:$14,482
Remarks: Gulf-Front Elegance | Sea Gate Club #10F | Longboat Key —Welcome to Sea Gate Club #10F, a rarely available 10th-floor end unit offering spectacular, front-row Gulf views in one of Longboat Key’s most intimate beachfront communities. Perfectly positioned mid-island along the sandy shores of the Gulf of Mexico, this elegant 2-bedroom, 2-bath residence captures direct, unobstructed views of the turquoise waters and mesmerizing sunsets from nearly every room. As a corner unit, it’s bathed in natural light and offers enhanced sight lines—creating a bright, open, and serene coastal retreat. Step onto your private balcony and take in over 350 feet of secluded beachfront, where dolphins, manatees, and colorful marine life glide through the waves just beyond your door. Inside, you’ll find a blend of comfort and coastal sophistication, ideal for relaxing or entertaining. Sea Gate Club is a boutique community of just 89 residences spread across 15 stories, offering a uniquely quiet and refined lifestyle. 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, and elevator doors. Additional enhancements are already in motion, with a new AC tower coming in 2025 and a sun deck scheduled for completion in Summer 2025—all fully paid for by current owners, totaling over $100K/unit. 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. Ideally located, Sea Gate places you just steps from Publix, CVS, and Bayfront Park, where you’ll find pickleball, tennis, shuffleboard, a playground, and kayak launch. Boaters will appreciate proximity to Longboat Key Moorings and nearby marinas, while St. Armands Circle—just three miles away—offers an upscale mix of dining, boutique shopping, and laid-back coastal charm. Here, you truly get the best of both worlds: to the north, the natural beauty of Anna Maria Island, and to the south, the vibrant arts, culture, and dining of downtown Sarasota. Whether you’re soaking in sunset views from your balcony or exploring nearby island attractions, every day feels like a vacation. This is Gulf-front living at its finest—private, peaceful, and rarely available. Schedule your private showing today and claim your slice of Longboat Key paradise.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-748-6300)
Listing Agent: Erica Thomas, Llc (941-799-9365)
2425 GULF OF MEXICO DR #14E, LONGBOAT KEY, FL 34228
$1,700,00040 Days on yellowkey MLS ID: A4686539
1 Days Off yellowkey (back on 4/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1470 Built: 1973 Tax: $13,728 (2025)Community: Sea Gate ClubSpa: YesCondo
Taxes:$13,728
High School: Riverview High
Remarks: Under contract-accepting backup offers. Amazing and Unobstructed 14th Floor Gulf and Beach Views! This is the perfectly remodeled unit you've been waiting for, with stunning sky views! Open floor plan, tile floors throughout, gorgeous open kitchen, and split bedroom floor plan. Just move right in and enjoy the views and amenities. The building has been completely remodeled. New roof, new windows, new railings, new pool, new storage lockers, updated elevators, new parking lot paving. NO PENDING SPECIAL ASSESSMENTS! Every owner has paid over $130K in the last 5 years to update the building and facilities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Robert Delaney (941-315-3185)
4360 CHATHAM DR #305, LONGBOAT KEY, FL 34228
$338,900100 Days on yellowkey MLS ID: A4678390
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969 Tax: $4,654 (2024)Community: Longboat HarbourSpa: NoCondo
Taxes:$4,654
Remarks: Waterfront living made easy! This furnished 1-bedroom, 1-bath condo is move-in ready and features beautiful tile flooring throughout, an updated kitchen, and an enclosed lanai perfect for relaxing. Just steps to the beach and loaded with amenities including four heated pools, private gated beach parking with pavilion and restrooms, beach chair storage, pickleball and tennis courts, and boat docks available for a minimal annual fee (up to 34’ boats). Enjoy a fitness center, billiards and card rooms, arts studio, and a banquet hall for social events. New roof already paid for. Priced to sell—don’t miss this affordable slice of waterfront paradise! ????
Listing Agent: Malihe Karimi (941-376-5099)
4955 GULF OF MEXICO DR #101, LONGBOAT KEY, FL 34228
$5,650,00040 Days on yellowkey MLS ID: A4686511
0 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3122 Built: 2007Monthly Fee: $6,860 Tax: $23,380 (2025)Community: PositanoSpa: YesCondo
Taxes:$23,380
Remarks: Completely redone with the highest detail to finishes just finished in 2025! Spectacular walkout to the beautiful beach and azure Gulf of Mexico from this first floor beachfront condo that features a private pool and spa. Positano, a 10 acre oasis with only 29 residences, has a full time security and a gated entrance. This is Florida living at its very best! A fantastic wrapping terrace on the gulfside offers outdoor enjoyment from the main living area and master suite with steps leading down to the private pool. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom all with private baths is 3343 square feet. A Gulf front gourmet kitchen with state-of-the art appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows dramatically overlook the Gulf of Mexico and beach. This home has a private elevator which leads to a home with beautiful wood floors, 10 foot ceilings, crown molding and comes with a private enclosed over size garage. The Owners' Club amenities include a state-of-the-art fitness center, catering kitchen, lounge with a fireplace, Plasma TV and surround sound system. There is a 75 foot olympic pool and spa plus outdoor grilling and shaded cabanas. The grounds are lush with tropical foliage and meticulously maintained
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
1241 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$950,00058 Days on yellowkey MLS ID: A4684166
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 940 Built: 1996 Tax: $8,141 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$8,141
Remarks: This unique plaza level Water Club residence offers you the convenience of stepping out to the exceptional Water Club amenities and lush grounds that lead to the sandy beach and azure waters of the Gulf of Mexico without the use of an elevator. This spacious 1 bedroom special residence features high 10 foot ceilings and the openness is enhanced by the floor to ceiling windows that captivate the tropical Florida landscaping. This home feels and lives like a beach house and sliding glass doors opening to the terrace complement this feeling by extending the living space to the outdoors and the serene setting. The indoor space is open and flows seamlessly from the living room area to kitchen space which also has a separate eating area open to the balcony and outdoors. The kitchen has granite countertops and high end cabinets and is designed to accommodate the joys of cooking. The floor plan offers privacy for the spacious master suite with a private terrace, elegant master bath and walk-in closet with a dressing area. There is also generous storage area in the condo. The Water Club is a premier Gulf front condominium with exceptional amenities and services. The designer decorated Club House features a professionally equipped gym and his and her spa areas, wine storage, billiard room, library, sunset bar plus a grand ballroom for special and formal occasions and gourmet catering kitchen. When not enjoying the beach, there is a heated elevated beautiful pool and hot tub with plenty of seating plus 4 Har-tru tennis courts. This condo location can also be used as a guest suite to be enjoyed by family and guests. The Water Club is conveniently located just minutes from award winning restaurants, Publix and CVS, St. Armands Circle, downtown Sarasota plus the Longboat Key Club for golf, tennis and restaurants is also nearby.
4995 GULF OF MEXICO DR #500, LONGBOAT KEY, FL 34228
$5,895,000103 Days on yellowkey MLS ID: A4677613
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3344 Built: 2007 Tax: $47,519 (2024)Community: PositanoSpa: NoCondo
Taxes:$47,519
Remarks: Step right into the epitome of Florida beachfront luxury with this stunning first-floor Capri unit on Longboat Key. Nestled within the exclusive Positano community—an intimate 10-acre oasis of just 29 residences—this condo offers a seamless walkout straight to the pristine beach and the azure waters of the Gulf of Mexico. This is Florida living at its finest. The condo features a fantastic wrap-around terrace on the Gulf side, perfect for soaking in the outdoor splendor from morning coffee to sunset cocktails. The primary suite offers direct steps down to the private community pool, while additional terraces off the secondary bedrooms ensure both privacy and gorgeous views. Spanning a generous 3,343 square feet, this true three-bedroom, all en-suite residence boasts a Gulf-front gourmet kitchen with state-of-the-art appliances, an adjacent family gathering area, and an open-plan flow from the living room to the dining space. Floor-to-ceiling windows frame dramatic views of the Gulf and the beach, while beautiful porcelain tile floors, 10-foot ceilings, and crown molding add to the sense of refined elegance. You'll enjoy the convenience of a private, enclosed two-car garage and the exceptional amenities of the owner's club, including a state-of-the-art fitness center, catering kitchen, and a lounge with a fireplace, plasma TV, and surround sound. Outdoors, there's a 75-foot Olympic pool, spa, grilling area, and shaded cabanas, all set amidst lush tropical landscaping. Truly, this condo is as close to the beach as it gets on Longboat Key.
4561 GULF OF MEXICO DR #202, LONGBOAT KEY, FL 34228
$2,750,000135 Days on yellowkey MLS ID: A4674911
REDUCED by $200,000 (6.8%) on 04/20/2026
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3260 Built: 1999 Tax: $29,736 (2024)Community: The Grande At Longboat KeySpa: YesCondo
Taxes:$29,736
Remarks: Spectacular North west corner three bedroom condo with direct beachfront views at The Grande, a oasis with only 8 residences. This is Florida living at its very best! This second floor corner location has breathtaking views of the Gulf of Mexico and miles of beautiful sandy beach plus some views of Sarasota Bay and amazing sunsets. A fantastic wrapping terrace on the Gulfside offers outdoor enjoyment from the main living area and master suite. Two other terraces off the additional bedrooms with privacy and wonderful views. This true three bedroom, all with private baths, is 3260 square feet. A Gulf front gourmet kitchen with high end appliances has an adjacent family gathering area. The open plan flows from the living room area to the dining room and the floor to ceiling windows that dramatically overlook the Gulf of Mexico and beach, enhance the brightness and open feeling of this home. This home has 10 foot ceilings, and comes with a private enclosed two car garage with direct access.This Longboat location is near many outstanding restaurants and Anna Maria Island. Watch dolphins and manatees and so many Florida birds glide past your backyard. The azure waters of the Gulf of Mexico and the beach are just steps away.
340 GULF OF MEXICO DR #115, LONGBOAT KEY, FL 34228
$2,345,000138 Days on yellowkey MLS ID: A4674650
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2314 Built: 1991Monthly Fee: $3,033 Tax: $16,082 (2024)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$16,082
Remarks: Your Longboat Key oasis awaits! This totally renovated 3bdrm 2.5 bath condo offers a open concept living space with high ceilings and walls of glass allowing sweeping views os Sarasota Bay. Light and bright material selections mix modern luxury with a coastal theme. The gourmet kitchen features white soft close custom cabinetry, sleek glass doors, quartz countertops, mother of pearl backsplashes and new stainless steel appliances. The open and inviting great room/dining room features separate wine coolers for varieties, a bar with open glass shelves and a cozy linear gas fireplace. The primary retreat offers luxury and seclusion with sliding doors onto the bay front lanai: a perfect place to watch the sunrise over the Sarasota skyline and enjoy playful dolphins and soaring seabirds. There is abundant walk in closet space customized by California Closets. The bath features a stand alone soaking tub and marble spa shower.custom cabinets, make up vanity, dual sinks and sparkling chandeliers complete the carefully curated mix of luxury and livability. The en suite guest bedroom features an open spa shower affording vacation style comfort to your guests. The third bedroom/office includes a wall of glass with retractable shade allowing for versatility of use. Notable home features include fine detail is such as wide plank LVT flooring throughout, 8’ solid mahogany doors with Emtek hardware, level five drywall finish, custom trim and millworker, LED recessed lighting, designer chandeliers, new high impact hurricane windows and sliders, and electric hurricane shutters throughout for peace of mind. Unique amenities include an attached oversized two car garage, an expanded courtyard off the kitchen with a seating area and your OWN gas grill. Residents have exclusive access to the Bay Isles Beach Club as well as on site amenities including a resort style pool, tennis, pickleball, exercise room, kayak SUP launch, and fishing dock. Perfectly situated in the southern most bayfront location on Longboat Key next to Quick Point Preserve, it is an easy walk to marina, restaurants,St. Armand’s and the LBK Club
435 L AMBIANCE DR #J704, LONGBOAT KEY, FL 34228
$2,995,000151 Days on yellowkey MLS ID: A4673061
REDUCED by $200,000 (6.3%) on 04/13/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2634 Built: 1994 Tax: $20,474 (2024)Community: L Ambiance At Longboat Key Club Ph 02Spa: YesCondo
Taxes:$20,474
Remarks: Rarely available, this 7th floor, 3 bedroom, 3 bath condo with perfect east/west views offers total privacy. Relax, unwind, and enjoy the magnificent views of the pristine sandy beach and the blue waters of the Gulf of Mexico from this unit in L ambiance. Turn around to the east and watch the boats on Sarasota Bay, and enjoy the lush fairways of the Longboat Key Golf Club. This well-designed unit is very private and does not face any adjacent buildings. The kitchen has been opened to the living areas to take advantage of the views in both directions and to entertain effortlessly. Your large private terraces are the perfect setting for enjoying a morning coffee while viewing beautiful shimmering sunrises over Sarasota Bay, and then enjoying a cocktail with the sunset every evening over the sparkling Gulf of Mexico. The Gulfside master suite opens to outstanding panoramic Gulf and beach views. Beautiful wood floors flow seamlessly throughout the open floor plan, offering a casual, elegant feel to this home. Perfectly set behind the private gates of the Longboat Key Club, you are surrounded by all the L ambiance has to enjoy, including a resort style pool with lap lanes, spa, and splash pool located on a massive outdoor lanai with gazebos and abundant seating, 2 lighted Har-Tru tennis courts, fitness center, saunas, recreation room, on-site management with 24-hour security, walking trails and over 1,200 feet of pristine beach. Your move-in ready home is waiting for you to start enjoying the paradise we call Longboat Key.
775 LONGBOAT CLUB RD #304, LONGBOAT KEY, FL 34228
$1,215,000164 Days on yellowkey MLS ID: A4671935
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1602 Built: 1984Monthly Fee: $1,904 Tax: $5,841 (2024)Community: Beaches Of Longboat Key Ph-1Spa: YesCondo
Taxes:$5,841
Remarks: Live in this third floor Beaches of Longboat Key condo and enjoy a living maintenance free lifestyle. Located on the southern end of Longboat Key behind the gates of the Longboat Key Club, this spacious two bedroom two bath condo in the unique 04 stack has magnificent full Golf course views from every room. This lovely residence has hurricane code sliding glass doors that open to the expansive terrace . The double door entrance opens to a private foyer and beyond is the living area plus adjacent granite kitchen with an eating area. There is also a dining room. The split floor plan separates the master suite from the two guest suites. The Beaches building has recently been renovated and has a welcoming and beautiful lobby plus upgraded hallways. Amenities include 24 concierge service, an on site manager, fitness center, two tennis courts, a fabulous Gulf side pool plus a spa. The private beach access leads to the sandy shores of the Gulf of Mexico with a private sitting area with lounge chairs and umbrellas. The Beaches is minutes from St. Armands Circle for enjoying fine dining and shopping and easy access to downtown Sarasota for the arts and theatre plus shopping and dining. Garage parking is private located under the building plus there is lots of guest and extra parking and a private storage area. A Gulf front life style in Paradise!
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