Longboat Key, Florida listings for sale

$35,000,000 - Longboat Key, FL

845 Longboat Club Road Longboat Key, FL - A breathtaking tribute to the grandeur of Renaissance Venice, Serenissima—meaning “The Most Serene”—stands as one of Florida’s most revered residences. With its coveted architectural detail and Gulf-front address, this palatial estate is unmatched in design splendor, craftmanship, and artistry. Gracing the southern tip of Longboat Key, endless views of sea, sand, and sky create an unforgettable backdrop for living. From the moment of arrival, Serenissima exudes elegance and beauty. A soaring marble hall crowned by a glass sky dome sets the stage for lively evenings with family and friends. Looking west, the shimmering Gulf of Mexico dazzles from nearly every room and stretches endlessly beyond the horizon. Majestic in scale yet intimate in nature, Serenissima offers grand spaces for lavish entertaining alongside serene retreats for private relaxation. Elements of bespoke design include a magnificent grand salon capable of hosting 100 guests, a gourmet chef’s kitchen perfect for gathering and conversation, a 10-seat home theater, and a light-filled sun room overlooking the infinity-edge pool. Six bedrooms and eight baths offer a private retreat for the whole family. Crafted with reverence for old-world artistry, the home features exquisite Venetian murals, dazzling chandeliers, and masterful millwork across three levels of luxurious living. For the car enthusiast, Serenissima’s ground level garage/car gallery comfortably fits 12 vehicles. Outdoors, the sophisticated architecture and landscape design perfectly complement the coastal location. Days here are filled with sun-drenched adventures—beachcombing, sailing, kayaking, or golfing —followed by unforgettable sunsets. Expansive terraces offer panoramic vistas over the pool, pristine beach, and shimmering turquoise Gulf waters. Located within the prestigious gates of The Longboat Key Club, members enjoy world-class amenities including golf, tennis, dining, a spa, fitness center, and a full-service marina. Just over the bridge, enjoy the world-class destinations of downtown Sarasota where opera, ballet, symphonies, and theater enliven everyday living. Serenissima is a one-of-a-kind legacy estate on Florida’s Gulf Coast, a stunning reflection of a life well lived.

$25,000,000 - Longboat Key, FL

5965 Gulf Of Mexico Drive Longboat Key, FL - Under Construction. A vision of architectural brilliance, this extraordinary estate, nestled on a nearly two-acre site on the Gulf of Mexico, is poised to redefine comfortable coastal living. Currently under construction with a cost basis of approximately $25 million, this landmark residence is destined to be one of the most iconic homes on Sarasota’s Gulf Coast. Conceptualized by internationally acclaimed Sweet Sparkman Architecture and Interiors, the design reflects a fusion of bold innovation, timeless elegance, and an intimate understanding of the coastal environment. The main residence is a masterpiece of refined sophistication, featuring an expansive primary suite with dual bathrooms and custom closets, a stately office, a dramatic foyer, and an open-concept great room leading to an elegant terrace with breathtaking views. Culinary enthusiasts will appreciate the convenience of dual kitchens — a main kitchen for entertaining and a chef’s kitchen for refined preparation — alongside a stunning wine cellar and formal dining room. Additional highlights include a lavish lounge, state-of-the-art cinema, multiple guest suites, a charming bunk room, a kitchenette for the guest suite level, and a breathtaking rooftop deck offering panoramic views. Complementing the residence is an exquisitely designed guest house as well as a pool house, creating a private retreat for guests and seamless entertaining. The estate’s exterior is equally fascinating, with lush, resort-inspired landscaping, tranquil water features, a tennis and pickle ball court and vast outdoor living spaces. The centerpiece is an enormous, shimmering pool, complete with a luxurious spa and an expansive deck offering countless options for alfresco dining and grand-scale gatherings. This exceptional estate embodies unparalleled craftsmanship and luxury. As construction progresses, the price will evolve, offering a rare opportunity to claim a bespoke piece of coastal elegance. Enjoy the ultimate island lifestyle on Longboat Key, renowned for its pristine beaches, tranquil ambiance, and world-class amenities. This idyllic retreat offers easy access to The Resort at Longboat Key Club, The St. Regis, St. Armands Circle, and the vibrant cultural offerings of downtown Sarasota. This extraordinary property offers the perfect balance of seclusion and connectivity in one of Florida's most sought-after destinations. Forbes Travel Guide’s Top 12 Destination for 2025 includes Longboat Key.

$23,950,000 - Longboat Key, FL

612 Juan Anasco Drive Longboat Key, FL - Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine land, this estate is a masterpiece of design and craftsmanship. Designed in the timeless British West Indies style, this home showcases vaulted ceilings, extensive trim detailing, white oak floors throughout, and two fireplaces, creating an ambiance of elegance and warmth. The expansive covered patios and porches invite you to embrace the serenity of waterfront living, while the heated pool and an impressive 13' x 13' hot tub serve as the ultimate retreats. A custom outdoor fire pit, two outdoor kitchens and indoor and outdoor pool tables elevate the entertainment experience. For boating enthusiasts, this estate is unrivaled, featuring four low-profile boat lifts. The largest lift accommodating vessels up to 30,000 pounds, the second lift is suitable for a vessel up to 20,000 pounds, and the third and fourth lift each have a 5,000 pound capacity, ideal for jet skis, kayaks, and paddle boards. Located just 10 minutes from the Gulf of America by boat and 5 minutes to Shore and Mar Vista restaurants, this is the perfect haven for life on the water. Inside, the Wolf Sub-Zero appliances provide top-tier performance in a gourmet kitchen built for culinary excellence. A Control4 smart home system offers seamless automation throughout, while HVAC-equipped garages ensure comfort year-round. The multiple garages can accommodate up to 9 cars, and the massive driveway can host 20+ vehicles. The residence boasts six spacious bedrooms, each with an en-suite bathroom, plus an additional full bath, and two half baths. Designed for both productivity and leisure, the home features his and hers offices, a media/theater room, a fully equipped gym, sauna, golf simulator, tackle garage, and a workshop. A private guest suite with a separate entrance includes a kitchenette, dining room, living room, bedroom, and bathroom, offering a luxurious retreat for visitors. With two state-of-the-art elevators, expansive landscaping, and a maintenance-free turf yard, this estate blends modern convenience with natural beauty. Ideally located near pristine beaches, world-class shopping, and gourmet dining, this estate is the epitome of waterfront elegance and exclusivity. Experience the pinnacle of coastal living--this is truly paradise found.

$19,500,000 - Longboat Key, FL

5861 Gulf Of Mexico Drive Longboat Key, FL - Welcome to 5861 Gulf of Mexico Drive, a contemporary home that exudes Zen-like calm in a tropical jungle garden located on over an acre beachfront estate on Longboat Key. This masterpiece of tropical modernism spans a stunning 1.1 acres with 100 feet of direct Gulf frontage, offering privacy, breathtaking views, and a sophisticated lifestyle experience. Seclusion and privacy begin with an eight ft solid concrete and Brazilian hardwood entry gate. Upon entering, you are welcomed down a path that leads you past two free standing accessory buildings that allow for multiple creative uses. The ground floor includes garage space for five vehicles, elevator lobby, social outdoor poolside areas, and storage. Continuing to the main structure, you are greeted by custom design to blend clean, modern lines with a warm, natural ambiance throughout the entire home. The home features custom finishes, including modern wide plank white oak wood flooring and a sleek natural silver travertine stone exterior for lasting beauty and resilience. The main living floor captures over 70 ft of glass showing off the Gulf views from every angle. The open concept plan provides gracious culinary space and a Chef’s kitchen. Featuring a 60” Wolfe gas range with double ovens, subzero fridge, freezer and wine storage. Two dishwashers, 5 ft gallery sink , expansive dark oak cabinets, open shelving and the large travertine dekton island for gathering and entertaining. Enjoy the meticulous hand crafted wine cellar for all your favorite wines. Glass sliders allow these zones to interface seamlessly with the adjacent outdoor deck areas. Comprised of four main components, the home is creatively connected to allow for a resort-style guest experience: main living, attached guest house with two suites with exterior entrances, attached bedroom wing with two bedrooms with ensuite baths, and owners top level. The floorplan incorporates natural light, communal gathering areas, private moments, and easy connections to the ever-present ocean views and sea breezes. The guests quarters are accommodated in four bedrooms with ensuite baths located off the main living areas. Connected by an exterior breezeway, the two guest bedroom suites are located under a separate roof for boutique hotel-style rooms and each include their own breakfast kitchen. The other two-bedroom suites are part of the main home and connected by a glass hallway. This wing has multiple sitting and TV areas for private lounge space for when needing a break from the main living. The upstairs is a true sanctuary—the entire level is dedicated to the primary suite, complete with a cozy seating area, coffee station creating the ultimate retreat with panoramic Gulf views. Enjoy the spa-like outdoor soaking tub and outdoor fire pit for an ambiance you just can not beat. Designed for both relaxation and activity, this estate includes a 75ft lap pool, lush landscaping, over 2,500 sqft of pool with integrated spa and panoramic Gulf views. Step out onto the 17x75 foot balcony equipped with a built-in grill, ideal for entertaining while taking in the expansive coastal scenery. Every inch has been crafted to foster both elegance and functionality, making it more than just a home—it’s a lifestyle. Step right outside onto the gorgeous white sandy beaches and sunsets every night. To truly experience firsthand the way this property can make you feel, where every moment feels like a vacation, schedule your private showing today.

$16,995,000 - Longboat Key, FL

6489 Gulfside Road Longboat Key, FL - Under Construction. Enjoy the ultimate Longboat Key lifestyle in your very own direct Gulf Front private access with stunning Gulf of Mexico views! The progress at this Seaward Homes Curated Collection at 6489 Gulfside is moving right along, with completion expected by August of 2025. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail. Situated on a coveted 100' Gulf front lot, this property offers soft sands, endless Gulf views, and miles of walkability. Gulfside Drive provides a quiet entrance street for its Gulf front residents. The main house features 4 oversized en-suite bedrooms and over 6,600 sq ft of air-conditioned living space, including a grade-level wellness room. The wide-open floor plan, oversized rooms, and large impact-rated safety glass sliding doors and windows throughout fill the home with natural light. Two nearly 40' long terraces on the main and second floors provide perfect spots to enjoy the outdoor island lifestyle and stunning Gulf views. Seaward Homes has partnered with premier Sarasota design company, Studio G Homes to bring luxury homes to the next level. Interior finishes include large format porcelain tile and hardwood flooring, Italian imported cabinetry, a custom floating steel and wood staircase, a 3-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Gaggenau appliance package, luxurious plumbing fixtures, wine storage, detailed AV, lighting control, and a security system. Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard premium aluminum architectural details, and a fine light sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a tropical landscape package. The garage accommodates 4 cars, with the option to add car lifts. Longboat Key, an 11-mile barrier island, is just minutes from St. Armand's Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and enjoy ultimate coastal luxury living.

$12,500,000 - Longboat Key, FL

50 Lighthouse Point Drive Longboat Key, FL - Discover the pinnacle of coastal luxury at 50 Lighthouse Point Drive, an extraordinary estate nestled in the exclusive gated community of Lighthouse Point. A 13-acre community with only 16 estate homes on Longboat Key. This residence on over 3/4 of an acre spans over 7450 square feet of living space, completely renovated beginning in 2015, offering six bedrooms, six-and-a-half baths, a game room, and a loft /study. The open-concept design embraces breathtaking panoramic water views from all sides, featuring three oversized floor-to-ceiling angles windows that frame the Gulf of Mexico, New Pass and Sarasota Bay. This unique personal resort-style residence features its own private beach & deck ideal for sandcastle building contest, a lush sprawling lawn to host a game of touch football and a new large pool & spa to cool down while enjoying a barbecue made in your new outdoor gourmet kitchen. Even the boaters can enjoy their very own private boat dock that can accommodate a 38 ft. boat & a set of jet skis! A tennis/pickle ball court is another Lighthouse Point amenity. Done with the outside, step inside to find an elegant entry foyer leading to a seamless flow between the living and family room both with soaring ceilings and expansive spaces create a sense of grandeur. The main living area highlights the updated primary bedroom suite and two additional bedrooms, an open bar with walk-in wine room, activity room large enough for a pool table, sitting area & wet bar. The gourmet kitchen with a center island is situated ideally for entertainment. The 3 -car side-entry garage has extra storage and new hurricane doors. A striking circular staircase with curved glass accents ascends upstairs to three large guest suites with en-suite baths plus a loft office/study with water views. Updates in the first half of 2024 include installation of a new flat tiled roof and hurricane-impact windows and doors. Additional storm protection measures include the concrete block construction and a seawall and sea groin on the beach. Become a member of the Longboat Key Club conveniently located next door to Lighthouse Point. Membership can offer 45 holes of golf, tennis and pickleball courts, five exceptional dining venues, a spa & fitness center, beach club and hotel suites. This is your rare opportunity to own a private beachfront estate that seamlessly combines luxury, location, and lifestyle.

$11,200,000 - Longboat Key, FL

435 L Ambiance Drive Longboat Key, FL - Introducing one of the most exclusive penthouses ever to come to market at L’Ambiance at Longboat Key Club. A rare chance to own a sky-high sanctuary in one of the most prestigious beachfront communities. Set against a backdrop of panoramic views stretching from the Gulf of Mexico to Sarasota Bay and the downtown skyline, this residence redefines coastal luxury. Spanning nearly 5,000 square feet, this move-in ready, impeccably maintained home is as functional as it is breathtaking, with a flexible 5-bedroom layout designed to comfortably accommodate large families or multiple guests. Whether you're hosting holidays, entertaining friends, or simply spreading out in style, this remarkable property delivers space, privacy, and elegance in equal measure. Step inside to discover soaring 13-foot ceilings, dramatic floor-to-ceiling windows, and multiple skylights that flood the home with natural light and amplify the spectacular, unobstructed views. Two expansive 75-foot terraces, one facing east, one west, offering private outdoor living with no neighboring buildings in sight, ideal for morning coffee, sunset dinners, or simply taking in the coastal breeze. The floorplan is both impressive and inviting, featuring a generous great room, formal dining area, office, bonus room and a spacious eat-in kitchen. The wet bar and great room area are perfect for relaxed evenings or lively gatherings, all set against the backdrop of sea and sky. The primary suite is a true retreat, featuring an en-suite bath, walk-in closet, and a nook perfect for your Peloton. Four additional bedrooms offer plenty of flexibility for guest suites. Additional perks include two prime garage parking spaces, an oversized climate-controlled storage room, and a private wine locker, ensuring effortless, secure living L’Ambiance offers true resort-style amenities: 24-hour security, concierge service, elevator access to your private foyer, guest suites, a heated lap pool and spa, Har-Tru tennis courts, a clubhouse with fitness center and sauna, and direct beach access. All of this, tucked behind the gates of the Longboat Key Club and just minutes from St. Armands Circle and the cultural epicenter of downtown Sarasota. A property of this scale, quality, and location is a rare find. A remarkable opportunity to step into elevated beachfront living, today.

$9,875,000 - Longboat Key, FL

641 Ranger Lane Longboat Key, FL - A luxurious coastal retreat at the water’s edge on Longboat Key, 641 Ranger Lane captures the essence of relaxed waterfront luxury. Set on a rare .42-acre corner lot with over 270 feet of prime waterfrontage, this coastal estate offers four bedrooms, 5.5 baths and 7,033 square feet of refined living space. With sweeping views from nearly every room, this home lives as beautifully as it entertains. A dramatic foyer and staircase introduce the home and the craftsmanship throughout. Travertine floors and dark crown molding flow through the main living areas, and a two-stop elevator adds effortless access to all levels. The open-concept great room appeals with a sleek linear fireplace and walls of sliding glass doors that frame the water, blurring the boundary between indoors and out. The beautifully designed kitchen was created with function and flow in mind. Two oversized islands feature seating, dual wine coolers, ice makers and generous storage. The professional-grade Sub-Zero refrigerator, Wolf cooking suite, custom pantry with a built-in coffee station complete with pot filler and coffee pod drawer, and hidden outlets throughout speak to thoughtful luxury. Start your day with coffee in the window-lined breakfast area and end it hosting guests in the elegant dining room with designer wallpaper, a statement chandelier and room to entertain. Step outside to experience island living through a series of outdoor vignettes. A covered area with a wood ceiling and built-in wet bar sets the stage for alfresco dining with coastal breezes. The infinity-edge pool appears to spill seamlessly into the water beyond. Nearby, a hammock sways between two coconut palms, while a fully equipped outdoor kitchen leads to a sunken fire pit lounge, near the seawall for unobstructed views of the bay. With a concrete seawall and ample room for a new custom dock and lift (waiting for installation date), the property is primed for water enthusiasts. The first floor also offers a bonus space— a bunk room—with soaring ceilings, coastal design and sliders to the pool deck. A guest suite features a walk-in closet, designer wallpaper and an en-suite bath. The adjacent laundry room includes quartz countertops, Whirlpool appliances, and generous storage. Upstairs, the primary wing is a sanctuary with double tray ceilings, a linear fireplace, and two private balconies with incredible views. The spa-inspired bath is clad in marble and features a soaking tub, a smart temperature-controlled shower with waterfall fixtures, a makeup vanity and a Toto commode. Dual walk-in closets are thoughtfully designed for form and function. A private office with a wood-paneled ceiling, tile flooring, and balcony access provides a peaceful workspace or retreat with serene water views. Hallways lined with windows of vistas lead to private guest suites with spa-like baths, balconies and water views. A second laundry room and full bath add everyday convenience. Experience the ultimate island lifestyle where coastal sophistication meets everyday serenity. In Longboat Key’s Country Club Shores community with deeded beach access and proximity to golf, tennis and boating, this home offers easy access to The Longboat Key Club, The St. Regis, St. Armands Circle and downtown Sarasota. Recently named one of Forbes Travel Guide’s Top 12 Destinations for 2025, Longboat Key is where waterfront living comes to life.

$8,500,000 - Longboat Key, FL

501 Harbor Point Road Longboat Key, FL - Rare opportunity to acquire completely remodeled waterfront residence (Finished in 2023) on Sarasota’s most prestigious barrier island of Longboat Key, in the coveted Harbors enclave of Bay Isles. Orchestrating exceptional style, comfort, and barefoot elegance, this five-bedroom home stirs the senses. Completely redesigned by renowned architect Clifford Scholz, construction was completed in October 2023 after two years. This home is filled with top of the line finishes that merge with a thoughtful floorplan and an endless list of custom touches. Set on a dreamy corner lot with basin frontage that leads straight into Sarasota Bay, the outdoor experience was perfected by award-winning landscape architect Michael A. Gilkey. Upon entering the foyer, your eyes are immediately drawn to the oil rubbed, hand scrapped wood floors and extensive woodwork throughout the entire home. The formal living room, anchored by a custom wormy butternut bar, coffered ceilings with hidden air vents and speakers and a wealth of french doors, which leads directly to the outdoor living room, protected by retractable screens and shutters. Enter the chef’s kitchen complete with Viking and Subzero appliances, Italian soapstone countertops, custom Campbell cabinetry, Miele built-in coffee station and ice maker in the beverage center, and two concealed Cove dishwashers. Rounding out the kitchen is the butler’s pantry with additional refrigerator, laundry, and custom cabinetry for storage of all your entertaining essentials. Enjoy morning coffee in the connected family room with gas fireplace and built-in bookshelves and cabinets. Conveniently located steps away is the large outdoor kitchen with grill, power burner, smoker, and custom dining table for twelve. Large media room contains custom leather theater seating and wet bar. Under the staircase is the climate controlled 506-bottle wine cellar with old-world marble floor. The breathtaking dining room includes custom built furniture imported from Italy, Juliet balcony, and wet bar. Two bedrooms finish out the first floor, one complete with custom built-in office. The pool bath has floating wood counters made from antique wooden boat slabs imported from France, mother of pearl shower wall tiles, and Waterstone fixtures. The primary suite is serene and spacious and opens to its own private terrace. Winding down every day becomes a cherished ritual in the primary bath which boasts large copper tub and Waterstone fixtures throughout, imported crema tile in zero clearance wet room that contains rain head, two handhelds, marble bench, and electronic privacy glass. The large ensuite closet is fully custom with mahogany wood slab island. A second-level primary bedroom offers an ensuite bath and its own private terrace. There is an efficiency bedroom, complete with ensuite bath with tub, and kitchenette with full-size fridge. The back yard pampers with a resort-like experience with pool with sun shelf, spa, custom firepit, outdoor shower and dog wash, and pet turf. The HOA maintains the seawall. The boat lift, jetski lift, and corresponding pilings are new, along with new Azek PVC decking material. Other notable items: 36,000 KW Kohler generator which powers the entire residence, Lutron smart home system, laundry room on each level of the home, three-car garage, and hidden retractable electronic Lutron shades throughout.

$7,995,000 - Longboat Key, FL

6381 Gulf Of Mexico Drive Longboat Key, FL - 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 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.

Longboat Key, Florida listings for sale

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