Displaying: For Sale
Location: Longboat Key
Property Type(s): Condos
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Longboat Key - 247 properties found
1135 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
$1,175,00034 Days on yellowkey MLS ID: A4694362
REDUCED by $125,000 (9.6%) on 06/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1503 Built: 1980 Tax: $13,396 (2025)Community: Beachplace ICondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,396
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDINARY PANORAMA! Come visit this property soon, as it boasts Two Parking spots, one in garage, near the elevator and one outside near the front door. Reimagined kitchen with lots of cupboard space, all KITCHEN AID appliances, 2019 Air Handler, never rented and barely occupied. Furnished with exquisite taste and comfortable living space! Beachplace is unique from other communities due to its high rental appeal for returning families! Enjoy the great Olympic size pool located in the center of the complex, plus the oversized hot tub, workout facilities, tennis courts, pickle ball and more! Not to forget the covered baby pool for ages 3 and under! The highest and most sought after units are always BEACHFRONT, holding the best value!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
2185 GULF OF MEXICO DR #212, LONGBOAT KEY, FL 34228
$1,995,00027 Days on yellowkey MLS ID: A4694656
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2448 Built: 1996 Tax: $15,129 (2025)Community: Villa Di Lancia Ph 1Spa: NoCondo
Taxes:$15,129
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Discover elevated Gulf-front living in this rarely available 3BR/3BA residence spanning 2,448 square feet in the prestigious Villa Di Lancia on Longboat Key. Perfectly positioned to capture panoramic Gulf views, this spacious condominium offers the ideal blend of privacy, security, and effortless coastal luxury. Expansive glass sliders, transom windows, and high ceilings fill the interiors with natural light, enhancing open living spaces designed for both relaxed living and entertaining. The great room flows seamlessly to a generous covered terrace, creating a year-round indoor-outdoor lifestyle. A unique private walk-out with spiral staircase provides direct access to the lush grounds, resort-style pool, and the pristine Gulf beach just steps away—an exceptional feature rarely found in condominium living. The well-appointed kitchen features a center island, solid surface countertops, and a casual dining area, perfectly suited for hosting family and guests. The primary suite serves as a tranquil retreat with terrace access, a sitting area, and a spacious bath with dual vanities, soaking tub, and glass-enclosed shower. Two additional guest bedrooms offer comfort and privacy. Villa Di Lancia is one of Longboat Key’s most sought-after beachfront communities, offering 440 feet of private beach, gated security, a beachfront lap pool and spa, fitness center, clubhouse, Har-Tru tennis courts, and pet-friendly living. The residence includes two climate-controlled garage parking spaces. Turnkey furnishings are available. Enjoy a lifestyle defined by convenience and sophistication—just minutes to the Longboat Key Club’s golf, tennis, and marina, the world-class shopping and dining of St. Armands Circle, and the vibrant cultural scene of downtown Sarasota, including fine dining, theaters, opera, ballet, and art galleries. Schedule your private showing today and experience the best of Longboat Key Gulf-front living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Steve Walter (941-809-0907)
1241 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$950,000118 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.
Listing is courtesy of: DEVELOPERS REALTY LBK, INC (941-799-9096)
Listing Agent: Reid Murphy (941-232-3304)
4995 GULF OF MEXICO DR #500, LONGBOAT KEY, FL 34228
$5,695,000163 Days on yellowkey MLS ID: A4677613
REDUCED by $200,000 (3.4%) on 05/11/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3344 Built: 2007 Tax: $47,519 (2024)Community: PositanoSpa: NoCondo
Taxes:$47,519
Tax Year: 2024
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
$2,750,000195 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
$2,345,000198 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
$2,995,000211 Days on yellowkey MLS ID: A4673061
0 Days Off yellowkey (back on 6/2/2026)
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.
1241 GULF OF MEXICO DR #603, LONGBOAT KEY, FL 34228
$3,295,000436 Days on yellowkey MLS ID: A4648856
Bed: 3 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 3045 Built: 1996 Tax: $27,359 (2024)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$27,359
Remarks: Welcome to this spectacular three bedroom 6th floor southern facing Brighton floor plan located in the south building of the sensational Gulf front Water Club complex on south Longboat Key. Your private elevator opens directly into the foyer which leads to the open floorplan and the sensational views of sandy beach and the Gulf of Mexico. The condo features beautiful wood floors, a gourmet kitchen with high end appliances, granite countertops plus a serene eating area. The spacious master suite is completely private with a large walk-in closet and elegant bath plus adjacent sitting area. The master has sliding glass doors leading to a private terrace with views of the Gulf of Mexico. The southern exposure of this condo bathes it in sunlight and stunning sunrises. The Water Club is a luxurious resort style complex on the beautiful sandy beach and azure waters of the Gulf of Mexico. The Water Club amenities include four tennis courts, a centrally located large pool and spa and a 24 hour staff plus gated access. The 17,000 sq.ft clubhouse features a spa and gym area separate for men and women plus a library and a catering kitchen and ballroom. The Water Club is conveniently located just minutes from award winning restaurants plus Publix and CVS, St Armands Circle, downtown Sarasota and the Longboat Key Club for golf, tennis and restaurants are also nearby.
2251 GULF OF MEXICO DR #301, LONGBOAT KEY, FL 34228
$5,999,000349 Days on yellowkey MLS ID: A4658325
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3921 Built: 2016Monthly Fee: $7,501 Tax: $69,970 (2024)Community: Aria Longboat KeySpa: YesCondo
Taxes:$69,970
Remarks: Welcome to an exceptional Gulf-front residence within the prestigious Aria community on the coveted south end of Longboat Key where refined coastal living meets timeless elegance. Set along 300 feet of pristine private shoreline, this extraordinary property offers a rare opportunity to experience true beachfront luxury in one of Sarasota’s most exclusive enclaves. Beyond the gated entrance, Aria unveils a serene, resort-inspired setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion that serves as the community’s elegant social centerpiece. This impeccably designed, residence spans nearly 4,000 square feet and is accessed via a private elevator, opening to a grand foyer and expansive, light-filled interiors. Recent enhancements include freshly painted cabinetry throughout the home. The thoughtfully curated open-concept floor plan seamlessly integrates sophisticated living and dining spaces with a chef’s kitchen, creating an ideal environment for both everyday living and elevated entertaining. Walls of floor-to-ceiling glass and soaring ceilings invite natural light while framing sweeping, unobstructed views of the Gulf. Expansive wraparound terraces provide the perfect setting to enjoy breathtaking sunsets and coastal breezes from nearly every room. The gourmet kitchen is a statement of both form and function, featuring premium quartz surfaces, freshly painted custom wood cabinetry, and top-tier appliances by Wolf and Miele. The primary suite serves as a private sanctuary, offering a spa-inspired retreat with dual baths connected by an oversized walk-in shower an exceptional design element rarely found. Two additional ensuite bedrooms provide luxurious accommodations for guests, while a dedicated office or optional fourth bedroom adds versatility. A bonus room offers additional flexibility for hobbies, media, or storage. Residents of Aria enjoy an unparalleled suite of amenities, including a beachfront pool and spa, state-of-the-art fitness and yoga studios, massage room, and a private wine cellar. A full-time onsite caretaker ensures a seamless, service-oriented lifestyle. The residence also includes a private, oversized two-car dehumidified garage. Don't miss the NEW video tour.
Listing is courtesy of: HOUSE MATCH (941-213-7028)
Listing Agent: Rachel Woodruff, Pa (941-705-8686)
1281 GULF OF MEXICO DR #111, LONGBOAT KEY, FL 34228
$1,050,00087 Days on yellowkey MLS ID: A4688079
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1392 Built: 1999 Tax: $9,956 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$9,956
Remarks: Welcome to a little piece of paradise on Longboat Key at the stunning gated Gulf-front condominium community of Water Club, which offers a coastal lifestyle complete with direct access to sandy beaches, high-end amenities and exceptional security and concierge services. This designer-inspired, two-bedroom, 2.5-bath condominium is on the newer north building's plaza level and features nearly 1,400 square feet, 10-foot ceilings, double crown molding, plank wood flooring in the living areas, natural colors and floor to ceiling storm impact windows and doors. An open floor plan offers garden views from the spacious living room and the kitchen, which has both a breakfast bar and a seating area. A beautiful kitchen renovation was completed in December 2025 with handsome wood cabinets, stone countertops and GE Profile appliances. The split plan allows privacy for owners and guests in the two separate primary en-suite bedrooms, each with large windows, custom drapes and carpet, wall closets with built-ins and baths with combination tub/showers. ?An expansive balcony with glass railing barriers can be accessed through the living area and one of the primary suites. This lovely condo conveniently has a stack washer and dryer, linen closet, underbuilding storage unit and assigned parking and its own front desk concierge. Behind the 24-hour guarded-gate is true luxury living with a modern clubhouse, state-of-the-art fitness room, locker room and spa, sauna, bar and lounge, library, game room, ballroom and catering kitchen and outside terrace for gatherings and watching sunsets over the Gulf waters. Besides the magnificent beach and Florida-friendly landscaped grounds, the outdoor amenities include a peaceful courtyard, fire pit, resort-style pool and hot tub and new Har-tru tennis courts. Water Club is conveniently near island golf courses and Publix, and a short distance from St. Armands Circle and downtown Sarasota for dining, shopping, entertainment and cultural venues.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kathleen Ucci (941-302-2344)
6750 GULF OF MEXICO DR #152, LONGBOAT KEY, FL 34228
$350,00090 Days on yellowkey MLS ID: A4686698
REDUCED by $5,000 (1.4%) on 06/02/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 990 Built: 1970 Tax: $2,215 (2025)Community: Whitney BeachCondo
Taxes:$2,215
Remarks: Bring your boat!!! Excellent water views in this north end desirable Whitney Beach waterfront community. If you’ve been waiting for the perfect second-floor residence in the highly sought-after Whitney Beach community on Longboat Key, this is the one. Offering some of the finest views in the complex, this turn-key condominium has been thoughtfully upgraded and is move-in ready. What truly sets Whitney Beach apart is its rare combination of resort-style living and relaxed island charm: Pet-friendly paradise — One of the few communities on Longboat Key that welcomes up to two large dogs, making it a dream for dog lovers. Private boat docks on the protected bayou, providing easy access to the water. One of the widest and most beautiful private beaches on the island, with direct deeded access. Resort-style heated and cooled pools for year-round enjoyment. Prime second-floor positioning that delivers the community’s best panoramic views. Unforgettable wildlife moments right from your home — watch mama manatees nurturing their calves in the canal and dolphins feeding just offshore. Convenient kayak storage and launch area. Exceptionally walkable location — just steps from upscale restaurants, shops, and a fitness center. One of the most pedestrian-friendly communities on all of Longboat Key. A thoughtfully designed floor plan with a low-density, intimate feel — no high-rise hotel atmosphere here. Spacious, peaceful surroundings where residents enjoy privacy and breathing room. Serene walking path to the iconic Beer Can Island (Greer Island), with its pristine beach and natural beauty. Just over the bridge lies Coquina Beach, home to vibrant weekly craft fairs and farmers markets. Nestled at the tranquil northern end of Longboat Key, this location offers the best of both worlds — easy proximity to the charming village atmosphere and world-class amenities of Anna Maria Island, one of America’s most treasured coastal gems. Don’t miss your opportunity to own a piece of this turquoise paradise at an exceptional value. Wake up every morning in one of Florida’s most exclusive island retreats — where luxury, nature, and relaxed coastal living come together perfectly.
Listing is courtesy of: COASTAL KEY REALTY LLC (941-993-9380)
Listing Agent: Amy Jones (941-993-9380)
3070 GRAND BAY BLVD #632, LONGBOAT KEY, FL 34228
$699,000598 Days on yellowkey MLS ID: A4627468
REDUCED by $25,900 (3.6%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1276 Built: 1995 Tax: $7,802 (2024)Community: Grand Bay 6Spa: YesCondo
Taxes:$7,802
Remarks: Move in ready and beautifully updated two bedroom two bath Bimini model in Grand Bay nestled within the secure gated enclave of Bay Isles. Located on the third living level of the four level over parking building 6, you will enjoy panoramic views of Sarasota Bay as you gaze out from your almost 400 foot wrap around terrace offering sunrise and sunset views. This particular condo has been tastefully updated with new variable speed HVAC with humidity control, Wi-Fi Thermostat & 12 year warranty on compressor in 2024; new water heater & significantly updated kitchen in 2026; new refrigerator, washer & dryer, Hunter Douglas battery operated remote-controlled window treatments, lighting & plumbing fixtures & freshly painted all in 2023. Nothing more to do but to move in and enjoy everything Grand Bay, Longboat Key and Sarasota have to offer especially with the recently renewed transferable Home-Tech service contract! Your amenities include two large resort style heated swimming pools and spas, tennis courts, state of the art fitness center and expansive clubhouse with social activities as well as access to the private white sandy well maintained beach at the Bay Isles Beach Club on the Gulf of Mexico. You will also have access to beautiful peaceful walking trails winding along the bay front, marina and golf courses. A short drive will lead you to choice eateries along Gulf of Mexico Drive or over the bridge to St Armands Circle and downtown Sarasota.
Listing Agent: Richard Perlman (941-228-8580)
3435 WINDING OAKS DR #18, LONGBOAT KEY, FL 34228
$949,000142 Days on yellowkey MLS ID: A4680403
REDUCED by $101,000 (9.6%) on 05/20/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2555 Built: 1988 Tax: $8,565 (2025)Community: Winding OaksSpa: NoCondo
Taxes:$8,565
Remarks: Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Listing Agent: Sean Clark (941-312-1146)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,600,000107 Days on yellowkey MLS ID: A4685503
1 Days Off yellowkey (back on 6/2/2026)
REDUCED by $150,000 (2.2%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2347 Built: 2024 Tax: $50,055 (2025)Community: St. RegisSpa: NoCondo
Taxes:$50,055
High School: Sarasota High
Remarks: Perched above the shimmering shoreline, this exquisite two-bedroom, two-and-a-half-bath residence at The St. Regis Longboat Key Resort offers breathtaking panoramic views of the turquoise waters of the Gulf of Mexico and the resort’s serene saltwater lagoon. Designed for both refined comfort and effortless coastal living, the residence showcases exceptional craftsmanship and sophisticated design throughout. A defining feature of this residence is the expansive private terrace, where all principal rooms open seamlessly to the outdoors. Complete with a gas grill, this exceptional outdoor living space provides sweeping views of the Gulf of Mexico and the tranquil lagoon—creating the perfect setting for al fresco dining, entertaining, or simply enjoying spectacular sunsets over the water. The gourmet kitchen is a true showpiece, appointed with sleek Poggenpohl cabinetry and premium appliances including Wolf double ovens, a gas cooktop, microwave, icemaker, and wine refrigerator. A generously sized island provides abundant built-in storage, making the space as functional as it is beautiful. This thoughtfully designed floor plan features two luxurious owner’s suites. The primary suite enjoys stunning views of the Gulf of Mexico and opens directly onto the large terrace. The spa-inspired bathroom features a large double vanity with elegant lighted mirrors plus a separate makeup vanity, two private water closets, a seamless glass shower, and a freestanding soaking tub. Electronic sheers and blackout shades provide effortless ambiance and privacy, while a custom-built closet offers exceptional storage. The second owner’s suite also captures captivating Gulf views and opens onto the terrace. Its spacious bath includes dual vanities with lighted mirrors, a water closet, and custom-built closets. Electronic sheers and blackout shades add both convenience and luxury. Additional highlights include a large laundry room with sink, cabinetry, and hanging rack, as well as an elegantly designed powder room for guests. Offered completely turnkey, the residence is beautifully furnished and enhanced with custom light fixtures throughout, creating a sophisticated yet inviting coastal retreat. Nestled within the first branded residential community and ultra-luxe 5 star resort on the Gulf of Mexico. The Residences at The St. Regis Longboat Key blend legendary service with the allure of a seaside getaway. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in residence dining. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
1050 LONGBOAT CLUB RD #901, LONGBOAT KEY, FL 34228
$1,400,00033 Days on yellowkey MLS ID: A4694717
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1974 Tax: $12,907 (2025)Community: Privateer NorthSpa: YesCondo
Taxes:$12,907
Remarks: Welcome to your beachfront retreat in the sky. Perched on the 9th floor of the highly desirable Privateer North community on Longboat Key, this beautifully furnished 2-bedroom, 2-bath residence offers 1,409 square feet of coastal elegance and breathtaking panoramic Gulf views from every room. Wake each morning to the sound of waves and endless turquoise water, and end each day with spectacular sunsets from the comfort of your living room, primary suite, or private balcony. The light-filled open floor plan is designed to showcase the stunning waterfront setting, featuring spacious living and dining areas that flow seamlessly to the balcony overlooking the Gulf of Mexico. The well-appointed kitchen offers quartz countertops, modern appliances, ample cabinetry, and everything needed for effortless entertaining. The spacious primary suite features direct balcony access, a king-sized sleeping area, and an updated en-suite bath, while the guest bedroom provides generous accommodations for family and friends. Both bathrooms have been tastefully updated with elegant finishes and walk-in showers. Just steps from the building, residents enjoy a secluded stretch of pristine private beach complete with beach chairs and umbrellas, as well as a large heated beachfront pool and spa with unobstructed Gulf views. Privateer North offers an exceptional resort-style lifestyle with a newly renovated fitness center, pickleball courts, shuffleboard, outdoor grilling and picnic areas, covered parking, secure entry, on-site management, and beautifully maintained grounds. Ideally located on the southern end of Longboat Key, this residence is only minutes from the upscale shopping, dining, and entertainment of St. Armands Circle and a short drive to downtown Sarasota, renowned for its arts, culture, waterfront parks, and world-class restaurants. Offering unmatched views, exceptional amenities, and one of the area’s most sought-after beachfront locations, this is coastal living at its finest. ** Seller is a licensed Florida Real Estate Agent
Listing is courtesy of: NINE LINE REALTY LLC (407-924-6353)
Listing Agent: Jamie Tillman (417-224-1917)
5591 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$900,00064 Days on yellowkey MLS ID: A4690629
2 Days Off yellowkey (back on 6/1/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1073 Built: 1979 Tax: $3,532 (2025)Community: Sea Club IiiSpa: NoCondo
Taxes:$3,532
Remarks: Under contract-accepting backup offers. Experience coastal living at its finest in this beautifully remodeled (2025) Gulf-front, ground-floor end unit at sought-after Sea Club III on Longboat Key. Sea Club III's daily and weekly rental flexibility accommodates those seeking to maximize rental income potential and/or enjoy that perfect personal retreat and getaway. No driving to beach parking lots or crossing streets for amenities required. Enjoy the convenience of direct Gulf beach access with powdery sands, soothing waters and breathtaking sunsets. All just steps from your covered patio. Heated community pool just steps from your front entry. Step inside to find fully furnished and updated interiors (2025). Impact double pane windows and sliders (2025) for added comfort and peace of mind. This condo offers both tranquility and accessibility. Sea Club III is just a short stroll to dining, cafés and parks. Located just minutes from St. Armands Circle and Downtown Sarasota’s dining, shopping and art scene. Convenient to SRQ airport with its ever-increasing direct flights to Sarasota. Do not miss out. This is truly a rare opportunity to own a piece of Old Florida!
Listing is courtesy of: WAGNER REALTY (941-761-3100)
Listing Agent: Gina Uliano (941-920-0276)
4127 GULF OF MEXICO DR #N102, LONGBOAT KEY, FL 34228
$4,700,000146 Days on yellowkey MLS ID: A4680618
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3521 Built: 2007 Tax: $30,723 (2025)Community: La FirenzaSpa: NoCondo
Taxes:$30,723
Remarks: Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.
1065 GULF OF MEXICO DR #302, LONGBOAT KEY, FL 34228
$749,000643 Days on yellowkey MLS ID: A4624142
INCREASED by $130,000 (21.0%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1392 Built: 1981 Tax: $4,571 (2023)Community: Beachplace IiiCondo
Taxes:$4,571
Tax Year: 2023
Remarks: One of a kind, never rented, ready for a new owner to put their touches on this opportunity! Unit has endless views. Come look, Being able to rent this unit, by the month, twelve times a year, that offers our beautiful GULF BEACH within seconds of the front door is incredible! Our third floor views are breathtaking, yet fully protected from the elements. Our Building is quiet, but close to BEACHPLACE amenities! Owners are motivated to sell and we can give you a complete tour when you visit. Also new HURRICANE Windows recently added. BONUS TWO PARKING SPACES, ONE IN GARAGE,ONE OUTSIDE! BEST VALUE IN BEACHPLACE BY FAR> GO COMPARE!
2301 GULF OF MEXICO DR #12N and 11N, LONGBOAT KEY, FL 34228
$2,377,000187 Days on yellowkey MLS ID: A4675054
REDUCED by $111,000 (4.5%) on 04/21/2026
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2415 Built: 1970 Tax: $13,538 (2025)Community: Islander Club Of LongboatSpa: NoCondo
Taxes:$13,538
Remarks: Rare Beachfront Opportunity - Two Adjacent Residences at The Islander Club, South Longboat Key Seize a truly rare and unique opportunity to own two adjacent Gulf-front residences in the North Tower of The Islander Club on South Longboat Key. Featuring highly sought-after southwest and northwest exposures, these first-floor walk-out condos live like a maintenance-free beachfront home, with no stairs or elevators and direct access from two private terraces to the Olympic-size beachfront pool and the private white sandy shores of the Gulf of Mexico’s crystal clear aqua waters. Combined, the residences offer 2,500+ square feet of Gulf-front living space, including four beachfront bedrooms and four full bathrooms, two balconies with over 500 square feet of total outdoor frontage, and expansive walls of glass showcasing panoramic Gulf views, brilliant sunshine, gorgeous sunsets, and refreshing cross-breezes. The layout functions as an expansive and seamless beachfront residence with flexible configuration options—combine both units into one refined Gulf-front luxury home, or live in one and rent the other, or tailor and customize the space for personal use or investment potential. Located directly on the beach in South Longboat Key, this one-of-a-kind legacy property is just three miles from St. Armands Circle and minutes from downtown Sarasota’s dining, shopping, and cultural attractions. Two covered parking spaces are included, along with additional guest parking available. The Islander Club features 400 feet of private beachfront, a new fitness and community center, beachfront pool, two Har-Tru tennis courts (soon to be remodeled for pickleball use as well), library, conference room, on-site management, gated access, and a highly advantageous and rare owner-to-owner rental program. Convenient to Publix, CVS, acclaimed restaurants, boutique shopping, and Sarasota’s renowned arts scene. Enjoy breathtaking Gulf sunsets and an unmatched Longboat Key beachfront lifestyle at one of Longboat Key’s most sought-after beachfront addresses.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Leah George (941-780-0597)
1105 GULF OF MEXICO DR #402, LONGBOAT KEY, FL 34228
$995,000314 Days on yellowkey MLS ID: A4661696
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1392 Built: 1981 Tax: $9,142 (2024)Community: Beachplace IiCondo
Taxes:$9,142
Middle School: Pine View School
Remarks: Beachplace at Longboat Key: Major price reduction for this Gulf-front luxury and rental-friendly, turnkey furnished investment opportunity! An iconic condominium in the mid-century modern style, Beachplace was constructed under the direction of Tim Siebert, one of the leaders of the Sarasota School of Architecture, and spans 31 acres with a quarter mile of Gulf beachfront. This price reduction makes this an ideal residence or investment opportunity. With a direct Gulf view, and a gentle walk to the beach, this two-bedroom, two-bathroom residence offers serene living; a spacious primary suite with ensuite bath, plus a guest suite, private balcony with stunning sunset views, full kitchen and dining and living spaces, new impact glass windows, all complemented by nearby amenities, including private beach access, a Junior Olympic-sized pool, spa, and a kid's pool. A clubhouse, two fitness facilities, a sauna, tennis, and pickleball courts, and two grilling stations complete the resort lifestyle. Electric Vehicle charging is on-site. The Resort at Longboat Key Club is immediately adjacent and offers championship golf and tennis facilities, a full-service marina nearby, and fine dining for its members and guests. St. Armands Circle shopping, dining, and entertainment is a short drive south, and Sarasota, with its thriving arts and cultural communities, eclectic shopping and dining, and extraordinary architecture, is a brief ride across the bay. Thirty-day minimum rentals are permitted twelve times annually. The buyer or their agent should review the possibility of any special assessments with the condominium manager. All of the information provided is considered reliable, but should also be verified by the buyer or buyer's agent.
Listing is courtesy of: DUNCAN REAL ESTATE, INC. (941-779-0304)
Listing Agent: Tom Aposporos (941-704-4250)
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