Refine Search
Map
Sort by
$1,475,000
2 Beds ⋅ 3 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code
One or more photo(s) has been virtually staged. Perched just one floor below the penthouse in the sought-after Grand Bay IV community on Longboat Key, this 2,550-sq.-ft. Cayman floor plan offers an exceptional opportunity to enjoy the Grand Bay lifestyle immediately. With ideal north–south exposure, this residence captures breathtaking sunrises over Sarasota Bay and stunning Gulf sunsets from two expansive terraces. Walls of glass and abundant natural light enhance the open-concept layout, which includes 2 bedrooms, 2.5 baths, and a den that can easily be reconfigured to include a walk-in closet for a 3rd bedroom. The primary suite opens directly to the Bayfront terrace, the second bedroom offers an en-suite bath and private Gulf-view balcony, and the den, kitchen, and third bedroom share access to a second terrace for effortless indoor-outdoor living. Two prime, side-by-side parking spaces on the upper main level sit conveniently next to the elevator, leading to a private elevator foyer. Residents of Grand Bay enjoy world-class amenities including 24-hour security, a clubhouse with library and game room, fitness center, tennis and pickleball courts, two heated pools and a spa, and deeded access to the exclusive Bay Isles Beach Club.

3010 Grand Bay Boulevard Unit 493, Longboat Key
$7,488,000
4 Beds ⋅ 5 Baths ⋅ Hideaway Bay Subdivision SubDv. ⋅ 34228 Zip Code
Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze. With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms. Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance. Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.

757 Hideaway Bay Drive, Longboat Key
$996,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Spectacular Gulf and Sunset views are enjoyed from this west facing Junior Suite in Building 3. The direct beach view through the swaying palms perfectly encompasses the resort lifestyle and the vision guests have of tropical landscapes when making reservations. This completely renovated residence is currently in the hotel program and reported healthy income in 2023 and 2024. 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 your Longboat Life today!

230 Sands Point Road Unit 3205, Longboat Key
$749,900
2 Beds ⋅ 2 Baths ⋅ Westchester Condo Apts SubDv. ⋅ 34228 Zip Code
Experience the epitome of Island living in this meticulously kept and beautifully renovated retreat located in the beachfront community of The Westchester on Longboat Key. This ground floor walk-out, 2 bedroom, 2 bath residence is a true coastal oasis all done up in seaside hues. The gorgeous kitchen opens to the large living/dining area and the spectacular views can be seen through impact resistant sliding doors that open wide for easy indoor/outdoor living. Step out to one of two private screened in lanais and you'll find the perfect spot to enjoy a morning coffee or an evening beverage while watching the sunset. This home is being offered with all the designer furnishings, so all you’ll need to do is bring your flip flops. Here you will find a remarkable quality of laid back island life with the gorgeous beach that stretches for miles, 2 sparkling pools, a tennis and pickleball court, a shuffleboard court, and a lovely clubhouse. An on site manager is available Monday through Friday. If you're ready for more, fine dining and nightlife in the world famous St. Armands Circle and the cultural mecca of downtown Sarasota are just a short drive away. Important to note: The pool area is currently undergoing a transforamtion and will include a new spa, a tiki hut and new landscaping when complete. Also important: The Westchester has completed its Milestone Inspection and all assessments have been paid in full.

4825 Gulf Of Mexico Drive Unit 105, Longboat Key
$845,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
This stunning 2 bed/2 bath residence comes turnkey furnished offering a full view of the Longboat Key Islandside Golf Course and partial views of the Gulf, Sarasota Bay, and the Sarasota city skyline through Hurricane Impact Sliders installed in 2024. The kitchen has been opened up to the living/dining area providing a beautiful view over the golf course greens while owners are creating culinary delights in the kitchen. There is a breakfast bar, a laundry closet, pantry, and plenty of solid wood cabinet space for storage. The primary suite pampers owners with access to the southeast-facing terrace along with a spacious primary bath offering dual vanities, an updated tile shower, and abundant closet space. The split floor plan allows for maximum privacy for both the primary and the ensuite guest bedroom. Other highlights include ceramic tile flooring throughout, stone counters, a coveted underbuilding parking space and an excellent rental policy of 1 month minimum 12 X per year. Beachplace offers a 24-hour manned guard gate, heated swimming pool & spa, tennis courts, dedicated pickleball courts, fitness center, clubhouse, on-site management, and miles of pristine beach to relax, enjoy and explore. Conveniently located on the south end of Longboat Key just minutes from the fine dining and shopping on St. Armands Circle and a short drive over the bridge to the cultural hub of downtown Sarasota.

1065 Gulf Of Mexico Drive Unit 402, Longboat Key
$1,299,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
This direct Gulf-front residence at Beachplace offers an extraordinary opportunity to enjoy the very best of Longboat Key’s beachfront lifestyle. Perfectly positioned to capture unobstructed views of the Gulf of Mexico, this furnished two-bedroom home combines a serene coastal retreat with strong rental potential—producing an average of $70,000 annually in gross rentals. Whether you envision it as your move-in-ready getaway, a property to personalize, or an income-producing property, the possibilities here are unmatched. From the moment you step inside, natural light fills the open floor plan. The welcoming foyer flows into a spacious living and dining area, framed by newer impact-rated walls of glass that extend to the private terrace. This expansive beachfront balcony is a highlight of the home, offering front-row seats to breathtaking sunsets, the sound of gentle waves, and refreshing Gulf breezes. The split-bedroom layout is designed for comfort and privacy. The primary suite enjoys direct terrace access, a large closet, and an en-suite bath with dual vanities. The guest bedroom is equally inviting and privately situated, ideal for hosting family or visitors. Additional features include tile flooring throughout, a well-appointed granite kitchen, and deeded parking—adding everyday ease for seasonal or year-round living. Life at Beachplace feels like a private resort. This sought-after community offers residents 24-hour staffed security, on-site management, a clubhouse perfect for a lively escape, along with Har-Tru tennis courts, a modern fitness center, and heated swimming pool with spa. Pristine beachfront access and lushly landscaped grounds create the ultimate Florida lifestyle. Located on the southern end of Longboat Key, Beachplace provides unmatched convenience. You’re just minutes from the Longboat Key Club’s golf and tennis facilities, the boutique shops and dining of St. Armands Circle, and the vibrant cultural venues of downtown Sarasota—including theaters, galleries, and waterfront parks. From beachside relaxation to world-class dining and entertainment, everything that defines Sarasota living is within easy reach.

1055 Gulf Of Mexico Drive Unit 504, Longboat Key
$950,000
1 Beds ⋅ 1 Baths ⋅ Inn On The Beach SubDv. ⋅ 34228 Zip Code
Highly desirable and rarely available 1st floor walkdown Junior Suite with Gulf views in Building 4 now available. This completely renovated unit is currently in the hotel program and reported healthy income in 2023 and 2024. There is an expanded deck in addition to the covered terrace, which provides direct access to the beach. Building 4 is situated farthest north on the gulf side where owners value privacy from the pool activities, but are still close to all of the amenities. 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!

240 Sands Point Road Unit 4102, Longboat Key
$995,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
Beachplace at Longboat Key: Major price reduction for this Gulf-front luxury and rental-friendly, turnkey furnished investment opportunity! Plus an incentive to buyers who reach a fully signed purchase and sale contract by July 15, 2026: a seller credit to the buyer in the amount of one year of the quarterly condominium association fees! 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.

1105 Gulf Of Mexico Drive Unit 402, Longboat Key
$699,000
2 Beds ⋅ 3 Baths ⋅ Northgate Of Longboat Key SubDv. ⋅ 34228 Zip Code
This rare offering is all about the one-of-a-kind BREATHTAKING VIEWS overlooking multiple waterways across Greer island, towards the Intracoastal and out to the gorgeous Gulf of Mexico sunsets! Situated on the quiet north end of Longboat Key in a boutique waterfront, building containing only 9 townhouse style residences: this is island living at its best! It features two bedrooms and 2 and a half baths plus a bonus ground floor air conditioned room and a workshop. Take the steps up to your first living level and enjoy a galley kitchen open to the large great room with sliders to one of 2 outdoor balconies above the ground level, poolside covered porch. On this level is also a half bath. Take the steps up to the second level and the views become even more astounding through the sliders from the Primary ensuite bedroom! Here you will also find the 2nd bedroom and the second bath. Besides the sparkling waterside pool, this small and friendly community has 3 small docks available that allow for easy water access with your kayak, paddleboard or small boat. And don’t forget it has its own clay tennis court as well. One of the nicest and widest beaches on Longboat Key is located just down the street and it wraps all the way around Greer island where you can stand and admire your condo across the waterway from your walk! Multiple restaurants and shopping destinations are within a bike ride or short walk away and the cultural epicenter of downtown Sarasota and Bradenton are just off island when you choose to leave. This may well be the laid-back island life style you are searching for.

490 N Shore Road Unit 6, Longboat Key
$1,350,000
2 Beds ⋅ 2 Baths ⋅ Sea Gate Club SubDv. ⋅ 34228 Zip Code
Price Reduced $100k—Welcome to Sea Gate Club #10F, a rare 10th-floor corner unit with sweeping, unobstructed Gulf views on Longboat Key. This 2-bed, 2-bath residence is filled with natural light and offers stunning sunsets from nearly every room—an ideal coastal retreat for relaxing or entertaining. Located in an intimate 89-unit beachfront community, Sea Gate Club offers a quiet, refined lifestyle with extensive recent upgrades, including impact windows, new roof, exterior renovation, pool, elevators, and more—no pending special assessments. Enjoy resort-style amenities: Gulf-front pool and spa, fitness center, tennis court, library, and social spaces, plus beachside extras like tiki huts and storage for bikes and water gear. Just minutes from St. Armands Circle, you’ll have easy access to dining, shopping, and island charm. Private, peaceful, and rarely available—this is Gulf-front living at its best.

2425 Gulf Of Mexico Drive Unit 10F, Longboat Key
$1,699,000
2 Beds ⋅ 2 Baths ⋅ Sea Gate Club SubDv. ⋅ 34228 Zip Code
BREATHTAKING WATER VIEWS FROM EVERY ROOM! Enjoy nightly sunsets from your private balcony in this beautifully updated 14th-floor condominium. This highly sought-after two-bedroom, two-bath split floorplan offers the perfect blend of privacy and open living. Each bedroom is positioned on opposite sides of the unit, creating an ideal layout for guests or remote work. Recent upgrades include Hurricane Impact Windows (2021), new flooring in both bedrooms (2021), updated bathrooms, fresh paint (2021), and an A/C system replaced in 2015. The convenience of an in-unit washer and dryer, a dedicated parking space, and ample guest parking add to the comfort of this coastal retreat. The beach and heated pool are just steps from your building, creating a true resort-style experience. Enjoy premium amenities such as a tennis court, air-conditioned bike room, kayak/paddleboard storage, clubhouse with kitchen, library/meeting space, and a fully equipped fitness center. Located within walking distance to Publix, CVS, places of worship, banks, the public library, and Town Hall. Just minutes to St. Armands Circle, where you'll find world-class dining and shopping. Immerse yourself in Sarasota’s rich cultural scene with easy access to the Sarasota Opera, Ballet, Ringling Museum, Selby Gardens, and numerous art galleries and theaters. This is your chance to live the Gulf Coast lifestyle—don’t miss it!

2425 Gulf Of Mexico Drive Unit 14B, Longboat Key
$749,000
2 Beds ⋅ 2 Baths ⋅ Beachplace SubDv. ⋅ 34228 Zip Code
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!

1065 Gulf Of Mexico Drive Unit 302, Longboat Key