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$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
$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
$2,750,000
1 Beds ⋅ 2 Baths ⋅ St Regis SubDv. ⋅ 34228 Zip Code
Incredible value at St. Regis Longboat Key. The last two one bedroom residences sold for $2,970,000 and $2,975,000. Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home. St. Regis Longboat Key offers a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail. An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds. Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents. This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulf side living.

1591 Gulf Of Mexico Drive Unit 216, 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
$1,699,000
3 Beds ⋅ 3 Baths ⋅ Sanctuary SubDv. ⋅ 34228 Zip Code
Nestled behind the exclusive gates of the Longboat Key Club, The Sanctuary enjoys an enviable location along a pristine stretch of Longboat Key’s Gulf beach. This exceptionally renovated 3BR, 3BA residence with nearly 2,400 square feet of living space is simply stunning. This corner residence features a thoughtful split-bedroom layout, elegant finishes and floor to ceiling high-impact glass leading to an open, wraparound terrace, where views of tropical palms and lush green space set the tone for outdoor dining, entertaining or a peaceful retreat. Inside, neutral tones with tasteful accents combine with walls of glass to create a bright, flowing ambiance. Trey ceilings, engineered hardwood flooring and tile in the baths add refined detail. The oversized kitchen is exceptional, with colorful cabinetry, stone countertops, and a large island with breakfast bar seating that opens seamlessly to the living room. Residents of the Sanctuary enjoy a recreational room, 24hr security guard, heated swimming pool, 2 Har-Tru tennis courts, and on-site management. Just steps away, the exclusive Longboat Key Club offers championship golf, a deep-water marina, a world-class spa, a private beach club, and fine dining, providing an unparalleled coastal lifestyle.

565 Sanctuary Drive Unit B106, Longboat Key
$769,000
2 Beds ⋅ 3 Baths ⋅ Fairway Bay 1 SubDv. ⋅ 34228 Zip Code
GATED, DEEDED PRIVATE BEACH ACCESS! This is a rare thing to be found on the keys! The main level with plantation shutters and hardwood floors includes the kitchen, dining and living areas. The kitchen has Subzero and Jenn-Air built in stainless steel appliances and granite countertops. A large second story skylight shines natural light through open ceilings onto the main floor dining area. The living area includes a fireplace and provides access to the back screened in lanai. Split bedrooms can be found on the 3rd level of the home. Both bedrooms have ensuite bathrooms and walk in closets. The owners ensuite bathroom includes dual sinks and a shower skylight. A heated pool is only steps away. Take advantage of the gym in the main clubhouse as well as the many amenities offered, including tennis. Membership to the Longboat Key Club is available for the ultimate Longboat Key lifestyle.

1926 Harbourside Drive Unit 1302, Longboat Key
$5,999,000
4 Beds ⋅ 5 Baths ⋅ Aria Longboat Key SubDv. ⋅ 34228 Zip Code
Rarely does a Gulf-front residence of this caliber become available within Aria, an ultra-exclusive enclave of just 16 residences on Longboat Key. Set along 300 feet of private shoreline, this extraordinary property offers an exceptional opportunity to experience true beachfront luxury in one of Sarasota’s most sought-after communities, complete with a newly added video tour. Beyond the gated entrance, Aria unveils a serene setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion serving as the community’s social centerpiece. Spanning nearly 4,000 square feet, this residence is accessed via a private elevator opening to a grand foyer and expansive, light-filled interiors with newly refreshed cabinetry throughout. The open-concept floor plan seamlessly connects living and dining spaces with a gourmet chef’s kitchen equipped with quartz surfaces and top-tier Wolf and Miele appliances. Walls of floor-to-ceiling glass and soaring ceilings capture sweeping Gulf views, while expansive wraparound terraces offer the perfect backdrop for sunsets and coastal breezes. The primary suite serves as a luxury sanctuary with dual baths connected by a rare, oversized walk-in shower, complemented by two guest ensuite bedrooms, a dedicated office or fourth bedroom, and a versatile bonus room. This residence includes a private, oversized two-car dehumidified garage, with access to Aria’s beachfront pool and spa, fitness and yoga studios, massage room, private wine cellar, and full-time onsite caretaker.

2251 Gulf Of Mexico Drive Unit 301, Longboat Key