Location: Longboat Key
Do Not Show Listings
6381 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$5,995,000125 Days on yellowkey MLS ID: A4678978
Bed: 4 Bath: 5.0 Gar: 9 Liv Area Sq Ft: 4224 Built: 2021 Tax: $94,565 (2025)Community: Sleepy LagoonSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$94,565
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: One or more photo(s) has been virtually staged. Welcome to a once-in-a-lifetime opportunity to own a sleek, modern coastal estate on one of Longboat Key’s most coveted stretches of sand. Perfectly situated on a rare double lot on the beach side of Gulf of Mexico Drive, this architectural gem incorporates uninterrupted, panoramic views of the Gulf. This completely turnkey furnished 4,420 square foot home has 4 bedrooms, 5 bathrooms and includes many upgrades showcasing incredible style. With nothing ever to be built in front, those golden sunsets and turquoise seas can be yours to savor forever. Built in 2021 with no expense spared, this home is a fortress of strength. Designed for durability by a structural architect, this home is constructed entirely of concrete utilizing sheer walls and concrete block combined with over-engineered pilings for peace of mind. Reglet trim has been achieved by utilizing metal steel framing , providing longevity and function. Inside, dramatic Euro-wall sliders blur the boundaries between indoors and outdoors, leading to a wraparound terrace that offers sweeping 260-degree views. A stunning elevated infinity-edge pool and spa, an outdoor shower and a fire table provide endless enjoyment. Level 5 drywall, oversized porcelain tile floors, and high design finishes elevate every corner. The main living level features a dazzling chef’s kitchen with European lacquer cabinetry, quartzite counters, and top-of the-line appliances: a 48” Sub-Zero fridge, 48” gas range, two ice makers, wine fridge, microwave drawer, natural gas service and more. Lutron LED lighting enhances the crisp, contemporary ambiance. The outdoor living is equally luxurious utilizing matching porcelain tile and a walnut-lined covered terrace to flow seamlessly from the interior. The top floor is a true penthouse master suite, leading to a self-contained oasis. The spa-like bathroom includes a soaking tub, a huge walk in shower and Gulf views from every room. An additional 1,150 square foot upper patio deck is framed by huge sliders allowing true indoor/outdoor living. In addition there is a second laundry room and kitchenette creating an amazing sanctuary. Whether used as a private refuge or separate guest quarters, this space can be closed off from the rest of the home, allowing the second floor, which includes 3 bedrooms and 3.5 baths, to be independently rented while preserving your own private haven. Three garages accommodate up to 9 vehicles, a gym and recreational toys. Leading outside is a large open area providing room to add a pickleball court or putting green. Beyond is over an acre of public land owned by the town of Longboat Key insuring your forever Gulf views. Additional perks include an elevator, two-zone A/C, dual laundry setups, gas tankless water heater, and electronic shades throughout. Currently operating as The Sea Grape Inn, this home offers income potential without sacrificing privacy, making it a rare hybrid of luxury retreat and smart investment. Step from your door to the sugar-white sands of Longboat Key and experience the pinnacle of Gulf-front living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
7030 POINSETTIA AVE, LONGBOAT KEY, FL 34228
$995,00068 Days on yellowkey MLS ID: A4686787
3 Days Off yellowkey (back on 5/1/2026)
REDUCED by $104,000 (9.5%) on 04/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1402 Built: 1934 Tax: $6,672 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$6,672
Elementary School: Anna Maria Elementary
High School: Bayshore High
Middle School: Martha B. King Middle
Remarks: Under contract-accepting backup offers. Enjoy as an investment opportunity or your own private retreat in the highly desirable Village neighborhood on the north end of Longboat Key, with no HOA fees and convenient Gulf Beach and Sarasota Bay access. Set on an oversized lot, the property includes a main residence and a separate guest cottage connected by an inviting breezeway, creating excellent flexibility for seasonal use or extended stays. Each space offers privacy and comfort, enhancing overall livability and guest experience. This turnkey furnished property has been thoughtfully restored to preserve its historic charm. Key updates include a metal roof, impact windows, new cabinetry, and updated appliances, providing both character and peace of mind. The main home welcomes you with an enclosed front porch and a warm, inviting living area complete with a wood-burning fireplace, pine wood flooring, and shiplap accents. The updated kitchen features striking countertops and extended workspace perfect for entertaining, with direct access to a private courtyard deck shaded by a majestic tree. The primary bedroom offers vaulted ceilings and a large walk-in closet. The primary bathroom is also tastefully updated. The guest cottage includes its own entrance, ensuite bathroom, private patio, and full kitchenette, making it well suited for guest accommodations or extended stays. Outdoor amenities further enhance the property’s appeal. A covered entertaining area overlooks the pool and spa within a screened lanai, complemented by a well-appointed covered outdoor kitchen. The spacious paver patio and lush tropical landscaping create a private resort-style setting that appeals to long-term or seasonal residents and guests alike. The oversized lot provides ample parking, including space for a boat or golf cart, an added benefit in this beach to bay community. With convenient access to a boat ramp, nearby beaches, waterfront dining and local shops, this charming neighborhood enjoys strong demand. Turnkey and ready to enjoy or generate annual or seasonal rental income, the seller is open to offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
380 GULF OF MEXICO DR #515, LONGBOAT KEY, FL 34228
$1,150,00096 Days on yellowkey MLS ID: A4683391
REDUCED by $49,000 (4.1%) on 04/30/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2380 Built: 1994 Tax: $11,342 (2025)Community: Tangerine Bay ClubSpa: YesCondo
Taxes:$11,342
Remarks: One or more photo(s) has been virtually staged. 2BD+DEN! Positioned as the southern-most community on Longboat Keys’ Gulf of Mexico Drive is the stunning Tangerine Bay. Its presence of pristinely manicured tropical color admired by all that enter the Key. Within this gated community lies #515- horizontal to Sarasota’s bayfront experiencing views that span across blue waters abundant with active sea-life. This 2bd/Den/2.5bath/2-car private garage home, with excellent wall space for displaying your finest art collection, extends over 2,300 square feet of living space. Courtyard entry, equipped with gas hook-up for your own grill, offers slider access into the kitchen/ family room area which is perfect for a different entertaining perspective since the courtyard is large enough to also accommodate table and chairs. Of course, the coveted place to dwell will be the grand living/ dining area and balcony to experience morning sun over the calming waters or the miracle of all the hues the sky can offer as the sun begins to set behind you. Large primary en-suite enjoys the water view and slider access to the balcony, considerably sized walk-in closet and super-spacious bathroom to create the spa-like atmosphere of your dreams. #515 will not disappoint with the generous kitchen, kitchen water filtration, split floorplan, updated windows and doors, 2024 remote roll-down hurricane shutters, 2023 A/C, 2026 water heater, roof and sprinkler heads replaced approx. three years ago. With a spanning lap pool, meandering lush lounging areas, spa, fishing/day dock, tennis/ pickleball, fitness center and clubhouse- Tangerine Bay is poised for pleasure to all who get to call it home. For a small annual fee, owners can also become members of the Bay Isles Beach Club.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Cindy Schatzle (941-587-7556)
550 YARDARM LN, LONGBOAT KEY, FL 34228
$3,775,000188 Days on yellowkey MLS ID: A4672604
0 Days Off yellowkey (back on 5/1/2026)
REDUCED by $20,000 (0.5%) on 04/28/2026
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4281 Built: 2006Monthly Fee: $23 Tax: $16,615 (2024)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,615
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Motivated seller ….ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of everyday life. Step inside and be instantly captivated by sparkling water views, soaring spaces, and the perfect blend of casual comfort and refined luxury. Designed for both relaxation and unforgettable entertaining, this 5-bedroom, 5.5-bath retreat is tailor-made for hosting family and friends in style. PRIME WATERFRONT LIVING - Private dock on a deep-water canal with no-bridge access to the bay, perfect for your weekend cruiser. LIGHT & BRIGHT OPEN LAYOUT - Walls of glass bring the outdoors in, filling the home with sunshine and stunning water views. ELEVATOR - Effortless access to main living levels from the three car garage. CHEF’S DREAM KITCHEN - High-end appliances, custom cabinetry, and an oversized island ready for gourmet meals and lively gatherings. LUXURIOUS SUITES - Owner’s retreat with a private balcony, spa-inspired bath, and dual walk-in closets. MOVIE ROOM - Your own private theater for cozy nights in. OUTDOOR OASIS - infinity pool, spacious patio, and lush landscaping for poolside lounging or sunset soirees. All this just steps to your DEEDED BEACH ACCESS and minutes from the world-class dining, shopping, and cultural treasures of St. Armands Circle and Downtown Sarasota. Whether you’re dreaming of a full-time Florida home or a seasonal escape, 550 Yardarm Lane delivers the ultimate Longboat Key lifestyle.
Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)
Listing Agent: Melanie Russell (941-879-5882)
925 SPANISH DR N, LONGBOAT KEY, FL 34228
$750,00033 Days on yellowkey MLS ID: A4691251
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1968 Tax: $491 (2025)Community: Spanish Main Yacht Club CondoSpa: NoVilla
Taxes:$491
Middle School: W.D. Sugg Middle
Remarks: Wow! Panoramic water views from almost every window, plus rare direct access to Bay waters just near the back paver patio. This completely renovated two-bedroom, two-bath, 1,449-square-foot home is a must see! Fully remodeled in 2025/2026 in full compliance with FEMA requirements. It is all about details as this gorgeous Spanish Main turnkey furnished villa is ready to welcome you home! The centerpiece of the kitchen is the large, strategically custom-designed quartz island that doubles as a dining table, in a soft color palette that can seat 10. The kitchen features beautiful all wood 42-inch cabinetry, stainless steel appliances, large undermount sink with a push-button garbage disposal, lovely backsplash and lots of storage with an abundance of additional counter space, ideally designed for entertaining. The villa flows seamlessly with an expansive open floor plan, plank tile flooring in every room plus crown molding that frames each room. The large primary bath has an oversized, classically designed walk-in shower created for handicap access with double sinks. The tastefully appointed guest bath has an all-glass enclosed walk-in shower. From guest bath, enter the 9-by-6-foot in villa laundry room with new Electrolux washer and dryer. All hurricane-grade windows and doors to secure the home from the Florida storms. Custom window shades provide sun mitigation and ultimate privacy. The fully enclosed glass Florida room is a treasure in and of itself with extensive views of Sarasota Bay, with a lush backdrop providing total privacy. There is also a built-in office space, large walk-in closet, additional flex space for dining and/or lounging plus a dry bar and wine center, which makes this a useful space. Go outside onto the brick paver patio and lounge, grill and relax with the sound and views of Bay waters and abundant bird and wildlife. Grab your kayak or paddleboard and launch right from the backyard with direct water access to the open Bay waters. This villa is packed with so many upgraded features with new tile roof in 2019, air conditioner in 2020 and tankless hot water in 2018. The villa is part of the Spanish Main Yacht Club community, which has some of the best waters to explore in Sarasota for fishing, sandbar enjoyment, kayaking and swimming right in your backyard. You have direct access to the Intracoastal Waterway and a quick boat ride to the Gulf of Mexico, with restaurants you can get to by boat. The Spanish Main maintenance-free community has a wonderful neighborhood feel with a heated pool overlooking the 40-slip marina, deeded beach access, with social events galore making every day feel like a vacation as you lounge in the sun and enjoy the sea breeze. Slips are available for affordable leasing. Beach access is ideal for those numerous beach days and magnificent sunsets. This pet-friendly very active 55-plus community are added benefits for your enjoyment. Only a short drive to the fantastic shops and restaurants including Anna Maria Island plus cultural events Sarasota and St. Armands Circle have to offer. Private second-deeded parking place with this villa.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Kimberly Freiwald (941-256-6775)
948 SPANISH DR S, LONGBOAT KEY, FL 34228
$1,199,00077 Days on yellowkey MLS ID: A4685572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1399 Built: 1968 Tax: $4,945 (2025)Community: Spanish Main Yacht Club CondoVilla
Taxes:$4,945
Remarks: Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. New tile roof in 2025. There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.
1241 GULF OF MEXICO DR #803, LONGBOAT KEY, FL 34228
$3,350,000230 Days on yellowkey MLS ID: A4667938
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3045 Built: 1996 Tax: $31,926 (2025)Community: Water Club 01 At Longboat KeySpa: YesCondo
Taxes:$31,926
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: The epitome of beachfront luxury awaits in this meticulously renovated 8th-floor residence at the prestigious Water Club on Longboat Key. This stunning 3-bedroom plus oversized study, 4-bath home is a rare offering in one of the Gulf Coast’s premier direct beachfront communities. From the moment you step off the private elevator into the foyer, you’re greeted by serene neutral tones, 10-foot ceilings, and wide-plank engineered hardwood floors that set the tone for elegant coastal living. Walls of glass frame spectacular, unobstructed views of the Gulf of Mexico, filling the expansive living spaces with natural light and breathtaking scenery. The open-concept floor plan seamlessly blends comfort and sophistication, enhanced by recessed lighting and a calming contemporary palette. The spacious living room flows onto a generous beachfront terrace—perfect for soaking in mesmerizing views and the soothing sounds of the surf. The designer kitchen is a showcase of modern design, featuring white glass subway tile backsplash, solid wood cabinetry, an induction cooktop with pot filler, Sub-Zero refrigerator, and premium stainless-steel appliances. A large center island and adjacent breakfast area provide the perfect setting for casual meals with sweeping water views. Each guest suite is a luxurious haven, including one with double queen beds and an en suite bath with soaking tub and separate shower. The third bedroom is currently configured as an office, yet spacious enough to accommodate a queen-size bed, and offers beautiful views of downtown Sarasota. The primary suite is a private retreat, featuring its own beachfront terrace, a separate sitting area, custom-fitted dual closets, and a spacious study with built-in office space. The spa-inspired primary bath is the essence of indulgence with white marble floors and walls, a freestanding soaking tub, and a glass-enclosed walk-in shower. Additional highlights include two under-building covered garage parking spaces, a private storage closet, and access to all the amenities of the Water Club—24-hour security, full concierge service, a resort-style pool and spa, Har-Tru tennis courts, fitness center, clubhouse with catering kitchen, and over 16 acres of pristine beachfront grounds. This is beachfront living redefined! Located just a short distance to St. Armands and downtown Sarasota's shopping, dining & cultural events.
1975 GULF OF MEXICO DR #G4-308, LONGBOAT KEY, FL 34228
$449,000238 Days on yellowkey MLS ID: A4666939
0 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1977 Tax: $5,438 (2024)Community: Seaplace IiiSpa: YesCondo
Taxes:$5,438
Middle School: Pine View School
Remarks: Under contract-accepting backup offers. 0.5 mi to Gulf beach access • Two heated pools & tennis courts • Gated Gulf-front community Welcome to Seaplace, a premier Gulf-front condominium community along Longboat Key’s scenic Gulf of Mexico Drive. This two-bedroom, two-bath residence (Unit G4-308) combines coastal living and community amenities in one of Sarasota County’s most desirable barrier-island locations. The open-concept layout flows seamlessly from the kitchen through the main living area to a screened lanai overlooking lush tropical landscaping and the Har-Tru tennis courts. Durable LVP flooring enhances the main living spaces, while neutral finishes allow a bright, airy feel throughout. The kitchen features ample cabinetry, and generous counter space for meal prep. The primary suite includes a walk-in closet and private bath; the secondary bedroom and full guest bath offer ideal separation for visiting friends and family. Convenient in-unit washer and dryer add everyday functionality. Residents of Seaplace enjoy approximately ½ mile of Gulf beachfront, two heated swimming pools and spas, a Gulf-side sundeck, Har-Tru tennis courts, walking paths throughout 42 acres of manicured grounds, a well-equipped fitness center, clubhouse with full kitchen and library, sauna, children’s playground, barbecue grills, and 24-hour staffed security gate. The quarterly association fee of $4,315 covers exterior maintenance, building insurance, water, sewer, cable, and amenities. Service animals are permitted per association rules; no pets otherwise. Seasonal and annual rentals are allowed with a two-month minimum. Situated along the island’s southern corridor, Seaplace offers proximity to both natural beauty and daily convenience. Publix (0.8 mi) and Bayfront Park Recreation Center (1.6 mi) provide easy access to groceries, pickleball courts, and a kayak launch. Fine dining options such as Harry’s Continental Kitchens (1.3 mi) and Euphemia Haye (1.1 mi) are nearby, along with The Shore Restaurant (1.9 mi) and the boutiques of St. Armands Circle (3.8 mi). Longboat Key Club Golf & Tennis (2.7 mi) and Downtown Sarasota (6.5 mi) offer world-class recreation and cultural attractions including the Van Wezel Performing Arts Hall, Ringling Museum, and Marie Selby Botanical Gardens. Seaplace’s Gulf-front setting provides direct beach access for sunrise or sunset walks, while community walking trails and tropical courtyards create a resort-style atmosphere year-round. This move-in-ready residence represents an exceptional opportunity to enjoy coastal living on Longboat Key, combining location, amenities, and Gulf access within a secure, well-maintained community. Includes interior laundry, screened lanai, and access to multiple pools, tennis, clubhouse, and beachfront amenities. Floor plan are available within the listing for additional detail.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
2045 GULF OF MEXICO DR #M1-502, LONGBOAT KEY, FL 34228
$469,500159 Days on yellowkey MLS ID: A4675820
1 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 928 Built: 1974 Tax: $6,201 (2025)Community: Seaplace IiCondo
Taxes:$6,201
Remarks: Under contract-accepting backup offers. A perfect coastal retreat located in Seaplace, and now at an unbeleivable price! This is one of Longboat Keys most desirable beachfront communities. A light and bright 2 bedroom, 1 plus bath, 5th floor condo with a beautiful Bay view. (the photos of the view just do not do it justice!) An exceptional location in the highly sought-after Gulf-front M1 building means you can have your toes in the sand in mere moments. It is beautifully turn-key furnished and meticulously maintained and is ready for its next appreciating owner. The large primary bedroom has its own private ensuite portion of the bath with a sink that can be shut off from a full bath, making it what one would call a 1 bath PLUS. The 2nd bedroom offers a perfect spot for visitors to help you enjoy this amazing way of life to the fullest. Seaplace offers resort style living with unmatched amenities that include 2 large pools and hot tubs; a kiddie pool; 3 har-tru tennis courts; a recently renovated Gulf-front clubhouse; a fitness center; library; gas grills; a one-mile paved walking path surrounding the lush 42-acre property, and a gatehouse with 24-hour security. Located near the newly opened St.Regis Resort, St.Armands Circle and the cultural epicenter of downtown Sarasota, you’ll be close to world-class restaurants, hotels, entertainment, arts, culture, and shopping. Come see this fabulous condo soon and make your island living dream a reality in 2026!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4340 FALMOUTH DR #D104, LONGBOAT KEY, FL 34228
$530,000142 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
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 Agent: Sharon Meier (407-927-5669)
2039 GULF OF MEXICO DR #G3-207, LONGBOAT KEY, FL 34228
$550,000328 Days on yellowkey MLS ID: A4657767
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1257 Built: 1974 Tax: $5,281 (2024)Community: SeaplaceSpa: NoCondo
Taxes:$5,281
Remarks: THIS IS THE LARGEST 2 BEDROOM 2 BATH FLOOR PLAN IN SEAPLACE! Located on the second floor (elevator access on the north end) of the G3 building, this home is move in ready! The previous den has been enclosed for a proper bedroom and updated! The primary bedroom and bathroom have both been updated. Updated lighting, updated baseboards, crown molding, no popcorn ceilings, no carpet, new hurricane rated sliders and windows! Plantation shutters are added for easy care and the coastal vibe! This building is located directly adjacent to the Har-Tru tennis courts, perfect for the avid player! Seaplace is a Gulf front community situated on lushly maintained grounds and offers not only tennis courts, a secure guarded gated entry, clubhouse, two heated pools/spas, fitness, Gulfside BBQ, organized social functions, onsite management and the icing on the cake is direct beach access! Residence comes completely furnished, assigned parking space #115, (north side of the building) Perfect for your second home and income protection, with a 2-month minimum rental period. Seaplace is located on beautiful Longboat Key convenient to grocery shopping, banking, and the best shopping on St. Armand's Circle! Or make a reservation at any number of first-class restaurants on the Key, and dine waterside, or find a nice cozy quiet booth inside and take in one of nature's most beautiful gifts of a sunset, and if you are lucky, you just may see the dolphins diving and playing! Come off the beach at the south end and you are immediately in downtown Sarasota, where you can catch any number of plays, or a live band for evening entertainment. The weekend offers a sidewalk Farmer's Market, with an assortment of vendors! Whatever time you have planned to be here, may just not be enough!!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
1581 GULF OF MEXICO DR #406, LONGBOAT KEY, FL 34228
$6,600,00078 Days on yellowkey MLS ID: A4685503
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: Lynn Morris, Pllc (941-400-4526)
408 GULF OF MEXICO DR #2112, LONGBOAT KEY, FL 34228
$35,000271 Days on yellowkey MLS ID: A4663562
Bed: Bath: 0.0 Tax: $397 (2024)Community: Boathouse On LongboatDock-Rackominium
Taxes:$397
Remarks: Welcome to Slip #2112 at The Boathouse on Longboat, a rare opportunity on the coveted south end of Longboat Key! This is your chance to secure a covered, hurricane-protected slip in one of Sarasota's most desirable waterfront communities. This slip accommodates boats up to 23'6''Lx8'6''Wx7'2''H (No T-tops unless collapsible). Enjoy first-class service at an affordable monthly rate with unbeatable amenities. Located just minutes from both Sarasota Bay and the Gulf, this facility offers on-site fuel, restrooms, a ship store, maintenance services, leasing assistance, and even the popular Dry Dock Waterfront Grill restaurant on site. Simply call ahead and your boat will be launched, fueled, and waiting for you. At the end of the day, return to dock and watch as the team expertly rinses and stores your boat in its covered slip. This is more than boat storage, it's effortless boating in paradise. Don't miss your chance to own high and dry covered storage on Longboat Key!
Listing Agent: Daniel Treiman (917-657-7495)
530 CHIPPING LN, LONGBOAT KEY, FL 34228
$5,799,00081 Days on yellowkey MLS ID: A4685275
Bed: 5 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 4216 Built: 2026Monthly Fee: $21 Tax: $16,910 (2025)Community: Country Club Shores Sec 02Spa: YesSingle Family
Taxes:$16,910
Remarks: Introducing the newest custom residence by Brista Homes, where exceptional craftsmanship and thoughtful design come together in a limited and highly refined offering. Nestled along a quiet canal in the sought-after waterfront community of Country Club Shores, this 4216 square-foot residence captures the essence of the Longboat Key boating lifestyle. With desirable south-facing rear exposure, tranquil canal views create a peaceful backdrop to daily living, while upper balconies frame beautiful views of Sarasota Bay. The home’s architecture, floor plan, and interior selections were curated by Brista’s in-house design team, drawing on years of experience building on Longboat Key and a deep understanding of what today’s waterfront buyers value most—timeless architecture, premium materials, and seamless indoor-outdoor living. A handcrafted iron pivot entry door framed by natural stone detailing creates a striking first impression. Inside, pocketing glass doors open the main living spaces to a resort-style outdoor setting where a custom salt water pool and elevated heated spa are surrounded by porcelain pavers and lush coastal landscaping. A fully equipped outdoor kitchen creates the ideal setting for entertaining along the water. At the heart of the home, the kitchen blends refined design with exceptional functionality. Custom Italian cabinetry is complemented by a dramatic Quartzite waterfall island and matching hood feature. A premium appliance suite by Miele — including a built-in refrigerator, integrated dishwashers, speed oven, and built in coffee maker — is complemented with a striking 48-inch dual-fuel range. A hidden butler’s pantry and custom wine display add both style and practicality for effortless entertaining. The great room centers around a sleek linear fireplace, creating a sophisticated gathering space. Upstairs, a spacious club room with a media wall and wet bar offers a relaxed setting for evenings with family and guests. Architectural details throughout the home include white oak plank flooring, a dramatic floating staircase, recessed baseboards, and clean modern lines that reflect a refined coastal aesthetic. Modern conveniences include whole-home audio, a whole house generator, multi-zone climate control, and integrated security. Located within one of Longboat Key’s most desirable boating communities, where deepwater canals provide quick access to Sarasota Bay and the Gulf of Mexico, this newly completed custom residence represents a rare opportunity to experience waterfront living defined by thoughtful design, exceptional craftsmanship, and enduring quality.
Listing is courtesy of: BRISTA REALTY LLC (941-373-0500)
Listing Agent: Gina Ursini (941-812-4894)
1930 HARBOURSIDE DR #145, LONGBOAT KEY, FL 34228
$549,00051 Days on yellowkey MLS ID: A4686987
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $50,000 (8.3%) on 04/22/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1982 Tax: $8,215 (2025)Community: Fairway Bay 1Spa: YesCondo
Taxes:$8,215
Remarks: Under contract-accepting backup offers. Set on the 4th floor of Building 1 in Fairway Bay, this beautifully styled 2BR/2BA residence captures sweeping views across the mangroves, a navigable channel and Sarasota Bay beyond—creating a vibrant waterfront backdrop from nearly every room. Upon entry, engineered wood flooring draws your eye to a wall of glass at the rear of the residence, where shifting blue and green tones take center stage. The layout flows effortlessly from the updated kitchen into the dining area and living room, allowing the view to remain the focal point throughout. The kitchen has been thoughtfully redesigned with striking stone countertops, low-profile white cabinetry, a refined tile backsplash and stainless-steel appliances. The living room opens to an expansive terrace through a full wall of sliders, offering a front-row perspective of the mangroves and channel, where boats pass by and manatees are often seen gliding through the water—creating a setting that feels both peaceful and connected. The primary suite serves as a private retreat with rich wood flooring, direct terrace access and a well-appointed bath featuring dual vanities and a separate water closet. The guest bedroom is comfortably sized, and the guest bath has also been tastefully updated. Residents of Fairway Bay enjoy a bayside lifestyle with deeded beach access through the private Bay Isles Beach Club, one underbuilding parking space, 24-hour gated security, walking trails, a heated pool, tennis courts and a fitness center. Membership opportunities at the Longboat Key Golf & Tennis Country Club and access to deepwater slips are available, and small pets up to 15 pounds are welcome.
Listing Agent: Bruce Myer (941-376-5311)
2120 HARBOURSIDE DR #623, LONGBOAT KEY, FL 34228
$1,095,00065 Days on yellowkey MLS ID: A4686721
REDUCED by $130,000 (10.6%) on 04/28/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2031 Built: 1988Monthly Fee: $137 Tax: $11,079 (2025)Community: Fairway Bay AtriumSpa: YesCondo
Taxes:$11,079
Remarks: Step into coastal elegance in this fully renovated three-bedroom, two-bathroom Fairway Bay residence, where every detail has been thoughtfully reimagined. A charming private lanai and seating area welcome you before entering the unit, setting the tone for relaxed waterfront living. Inside, an open-concept layout seamlessly blends the kitchen, dining, and living spaces, creating a bright, airy environment perfect for both entertaining and everyday comfort. The gourmet kitchen is outfitted with GE Profile appliances, custom soft-close cabinetry, and ample storage, offering both style and functionality. The primary suite is a serene retreat featuring a spacious walk-in closet, additional storage, and a beautifully updated en-suite bath with a large walk-in shower. From both the living room and the primary suite, step onto the expansive north-facing balcony to take in the tranquil Sarasota Bay views, where you can enjoy the morning sunrise and the soft glow of the evening sky. The second bedroom is generously proportioned and easily accommodates a king-size bed, creating a luxurious space for guests. The third bedroom is also spacious, complete with a custom built-in, ideal for a guest room, home office, or flexible living area. A thoughtfully designed guest bath ensures privacy and convenience for family or visitors. This unit also includes the ease and security of one covered parking space beneath the building. Fairway Bay residents enjoy an exceptional suite of amenities including two heated pools, a spa, a clubhouse, a fitness center, tennis and pickleball courts, and private beach access on Longboat Key. With the shops, dining, and vibrant lifestyle of St. Armands Circle just minutes away, this residence combines the best of convenience and refined waterfront living.
3080 GRAND BAY BLVD #515, LONGBOAT KEY, FL 34228
$625,000145 Days on yellowkey MLS ID: A4674001
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1276 Built: 1996 Tax: $7,834 (2024)Community: Grand Bay 5Spa: YesCondo
Taxes:$7,834
Remarks: Defined by an exceptional indoor–outdoor connection, this 2BR/2BA Grand Bay residence offers a lifestyle centered on expansive terrace living and refined interiors. The living room is wrapped in floor-to-ceiling glass and opens to a wide wraparound veranda, creating an airy, resort-style ambiance that seamlessly blends indoors and out. The open living area flows naturally to the dining space and kitchen, with double doors allowing the kitchen to be closed off for entertaining. Thoughtfully designed, the kitchen features all-white cabinetry, stone countertops and a clean, timeless aesthetic ideal for both everyday living and hosting. The primary suite is spacious and inviting, with corner sliders opening to the terrace and a well-appointed bath with dual vanities, a spa tub and a glass-walled shower. The guest bedroom is equally generous and enjoys direct terrace access. Outdoors, the expansive terrace offers unobstructed views of Sarasota Bay and the city skyline—perfect for entertaining, morning coffee or evening cocktails. Located behind the gates of Bay Isles, Grand Bay is a socially active, resort-style community offering a clubhouse, guard gate, two-car under-building parking, fitness center, two Har-Tru tennis courts, two heated pools, a spa and deeded access to the private Bay Isles Beach Club. Optional membership to the Longboat Key Club further enhances the lifestyle with championship golf, private beach privileges, a full-service marina, tennis and pickleball, a luxury spa, fitness facilities and acclaimed dining.
1065 GULF OF MEXICO DR #201, LONGBOAT KEY, FL 34228
$629,000215 Days on yellowkey MLS ID: A4669086
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1172 Built: 1981 Tax: $7,875 (2024)Community: Beachplace IiiCondo
Taxes:$7,875
Remarks: One or more photo(s) has been virtually staged. One or more video(s) was virtually staged. Sunny and rarely available 2-bedroom, 2-bath corner residence in BeachPlace III on Longboat Key. This desirable end unit offers a wraparound terrace and open views of lush tropical landscaping, the Longboat Key Club’s Links Golf Course, and partial Gulf views—providing excellent natural light and a true coastal feel. The residence features brand-new, impact-rated floor-to-ceiling sliding glass doors that brighten the living and dining areas and enhance indoor-outdoor living. The open-concept layout connects the kitchen, dining, and living spaces, making it well suited for everyday living or entertaining. A split-bedroom floor plan provides privacy, with the primary suite offering direct access to the terrace. One assigned parking space is included, and the unit is ready for personalization or updating. BeachPlace is a gated, Gulf-front condominium community offering 24-hour security and resort-style amenities, including a clubhouse, heated beachfront pool and spa, tennis courts, fitness center, and a private boardwalk with direct beach access. Seasonal beach service with lounge chairs and umbrellas is provided. Conveniently located near golf, marinas, dining, and shopping, and just a short drive to downtown Sarasota, this property offers flexibility as a full-time residence, seasonal getaway, or investment opportunity.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: John Esser (515-306-8505)
1000 LONGBOAT CLUB RD #204, LONGBOAT KEY, FL 34228
$949,000194 Days on yellowkey MLS ID: A4671838
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1409 Built: 1972 Tax: $6,901 (2024)Community: Privateer SouthCondo
Taxes:$6,901
Remarks: Sublime Gulfside Retreat at Privateer South — 1000 Longboat Club Rd #204 Experience the pinnacle of effortless beachfront living behind the prestigious gates of the Longboat Key Club. This immaculate, fully remodeled 2-bedroom/2-bath residence at Privateer South is offered turnkey furnished, presenting an immediate sanctuary of modern coastal style. Meticulously renovated with longevity in mind, the home is enveloped in impact-rated windows and sliders, ensuring quiet comfort, energy efficiency, and ultimate peace of mind. An inviting entry flows into a radiant, open-concept great room where living and dining zones transition seamlessly to the outdoors. Step onto your private covered balcony to take in unobstructed, panoramic views of the Gulf of Mexico— the ultimate backdrop for sunrise coffee, golden-hour cocktails, and the soothing sounds of the surf. Inside, cohesive coastal flooring and a sophisticated neutral palette provide an elegant canvas for personal style, accented by designer lighting and polished hardware. The renovated kitchen is a sleek culinary workspace featuring custom cabinetry, lustrous stone countertops, and premium stainless-steel appliances. The thoughtful split-bedroom layout guarantees privacy for owners and guests alike. The serene primary suite is a true retreat, offering extensive custom built-out wardrobes and a spa-inspired en-suite bath with a frameless walk-in shower. The oversized guest bedroom is equally impressive, boasting its own generous custom walk-in closet and adjacency to a second, well-appointed full bath. This residence is designed for a true "lock-and-leave" lifestyle, complete with abundant interior storage, an assigned covered parking space, and an additional dedicated storage locker. Privateer South provides an unrivaled resort experience on a pristine stretch of sugar-sand beach. Enjoy a Gulf-front heated pool and spa, tennis and pickleball courts, a modern fitness center, a vibrant clubhouse, on-site management, and 24-hour gated security, all framed by lush tropical landscaping. Comprehensive association services handle practically everything, supporting a stress-free ownership experience. Minutes beyond the shoreline lie world-class amenities: championship golf, a full-service marina, and fine dining at the Longboat Key Club (membership optional), the chic boutiques of St. Armands Circle, and the cultural vibrancy of downtown Sarasota. A rare blend of thoughtful renovation, storm-ready construction, and amenity-rich Gulfside living, Privateer South #204 is more than a condo—it’s an endless getaway.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mike Griffin (941-586-6402)
350 GULF OF MEXICO DR #211, LONGBOAT KEY, FL 34228
$938,500237 Days on yellowkey MLS ID: A4667037
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2394 Built: 1992 Tax: $9,083 (2023)Community: Tangerine Bay ClubCondo
Taxes:$9,083
Tax Year: 2023
Remarks: Experience resort-style living at Tangerine Bay Club, a gated sanctuary on the desirable south end of Longboat Key. This impeccably maintained end-unit residence offers 2,400 square feet of refined living space with lush Sarasota Bay views and unmatched proximity to the area’s top attractions. Minutes to St. Armands Circle, downtown Sarasota, and steps to Dry Dock Marina and Restaurant. No current assessments and meticulously maintained grounds. Thoughtful floor plan with multiple terrace access points to enjoy morning and afternoon sun. This three-bedroom, two-and-a-half-bath, plus den, includes an oversized private two-car garage. There is also a natural gas barbecue on the front terrace. Resort-style amenities at Tangerine Bay Club include a heated pool, lap lane, heated spa, tennis, and regulation pickleball courts, a clubhouse with a fitness center, and a vibrant social room and calendar (happy hours, pickleball, cultural excursions). Freshly renovated boat dock, two kayak launches, a fishing pier, and prime fishing directly on Sarasota Bay. Enjoy just “sittin’ on the dock of the bay” watching the dolphins roll in. Take a scenic nature walk between Sarasota Bay and Quick Point Nature Preserve. Ownership includes (optional) membership to the Bay Isles Beach Club facilities for just $600.00 per year (application required).Longboat Key is renowned for golf, tennis, fine dining, boating, and world-class fishing. Be sure to explore the newly opened St. Regis resort, just a short stroll to the north on the beach side. Ongoing management ensures a carefree ownership experience with no special assessments anticipated. Recent capital projects (painting, waterproofing, elevator rebuilds, 2024 roof replacements, exterior tile walkway updates) have been completed and funded, with milestone inspections cleared. Pet-friendly, gated entry, and a day dock for fishing. This residence offers the perfect blend of luxury, convenience, and peace of mind—an ideal retreat for those seeking sophistication and coastal living at its finest. DON’T JUST THINK ABOUT IT, COME EXPERIENCE IT FOR YOURSELF AND MAKE IT YOUR REALITY.
Listing Agent: Judy Kepecz-Hays (941-587-1700)
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