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$3,995,000
Bay Isles SubDv.
Discover the rare opportunity to create a legacy waterfront estate in the prestigious Harbor Section of Bay Isles, one of Longboat Key's most coveted boating communities. Tucked behind double gated, guard-secured entry, this exceptional 0.41-acre homesite boasts an impressive 135 feet of deep-water frontage, offering effortless access to Sarasota Bay and the Gulf of Mexico. Designed for those who embrace the waterfront lifestyle, the expansive canal frontage provides possibilities for multiple vessels and seamless days on the water. As a Bay Isles resident, you'll also enjoy deeded private access to the Bay Isles Beach Club, where miles of pristine Gulf beaches await. Perfectly positioned directly across from the world-renowned St. Regis Longboat Key Resort, this premier location places luxury amenities at your doorstep while maintaining the privacy and exclusivity of a gated waterfront enclave. Championship golf, marinas, waterfront dining, boutique shopping at St. Armands Circle, and the arts, culture, and fine dining of downtown Sarasota are all just minutes away. Whether you envision a contemporary coastal masterpiece or a timeless waterfront retreat, this remarkable homesite offers the ideal canvas to build the custom residence you've always imagined in one of Southwest Florida's most distinguished waterfront communities. Architectural plans are available upon request, with engineering complete. Capitalize on the extensive development work already completed, saving valuable time and expense while accelerating the path toward permitting and construction. An existing residence is situated on the property; however, the property is being marketed for its exceptional homesite and development potential.

1600 Harbor Sound Drive, Longboat Key
$1,999,000
5 Beds ⋅ 3 Baths ⋅ Country Club Shores SubDv.
Discover an exceptional chance to complete a vision of waterfront luxury in the highly sought-after community of Country Club Shores on Longboat Key. This canal-front home offers the rare opportunity to pick up where the current owner left off—finishing a sophisticated coastal residence with the majority of major structural work already completed. For discerning buyers seeking to capture immediate equity and create a bespoke waterfront retreat, this property represents outstanding value in prime Longboat Key real estate. Set on a spacious 110’ x 110’ canal-front lot, the home features a fully reconstructed seawall and a private dock equipped with a 13,000-pound Platinum Series boat lift, providing effortless access to Sarasota Bay and the sparkling Gulf of Mexico. The residence is framed for approximately 3,089 square feet under air, offering 5 bedrooms and 3 bathrooms in an elegant coastal ranch-style layout designed for seamless indoor-outdoor living. Substantial improvements have already been executed to the highest standards: a brand-new roof, complete framing, exterior walls, plumbing and electrical rough-ins, natural gas lines, insulation, HVAC ductwork, and impact-resistant windows and doors. Premium materials and finishes—including custom Italian cabinetry, Miele appliances, designer fixtures, and additional high-end components—convey with the property. Engineer-prepared plans provide a clear roadmap for completion, empowering the next owner to personalize the final touches while benefiting from the extensive work already invested. Located in one of the best positions within the desirable Country Club Shores community, this fixer-upper presents the perfect canvas to realize the seller’s vision of an amazing luxury waterfront home. Imagine waking to serene water views, launching your boat from your private dock, and enjoying the effortless Florida lifestyle that defines Longboat Key. Just moments away, enjoy world-class amenities and recreation: championship golf at the prestigious Longboat Key Club, pristine Gulf beaches for sun-soaked days, and the vibrant dining and shopping scene at St. Armands Circle. Explore Sarasota’s renowned fine and performing arts venues, upscale boutiques, and waterfront restaurants—all while residing in this sought-after enclave. Whether you crave boating adventures, cultural experiences, or relaxed coastal living, this location delivers unparalleled convenience and luxury. Don’t miss this unique opportunity to complete a standout waterfront property and unlock its full potential in one of Florida’s most desirable communities.

525 Sloop Lane, Longboat Key
$550,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv.
Experience the best of Longboat Key in this beautifully appointed coastal retreat, nestled within the highly sought-after 55+ community of Spanish Main Yacht Club! This newly remodeled 2-bedroom, 2-bathroom residence is offered fully furnished turnkey with all brand-new, high-end coastal furnishings. Ideally situated just steps from the active marina and a picturesque seawall—perfect for peaceful mornings, frequent dolphin and manatee sightings, and stunning bayfront sunrises—you'll also enjoy Gulf-side beach sunsets just a short stroll away. Thoughtfully designed, the home offers premium mattresses dressed in organic cotton linens and a fully stocked kitchen, providing a refined, move-in ready living experience from the moment you arrive. Residents enjoy access to a fantastic array of community amenities, including a private marina with available boat docks and kayak storage, deeded beach access, a heated community pool, and shuffleboard courts. Ideally located just minutes from the upscale dining and boutiques of St. Armands Circle and a scenic drive to Anna Maria Island, this property offers the perfect blend of active-adult tranquility and local accessibility. Whether you are boating, fishing, or relaxing in the bright, inviting Florida room, this is a rare opportunity to live the ultimate Longboat Key lifestyle.

914 Spanish Drive S Unit 76, Longboat Key
$450,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv.
Experience the ultimate Longboat Key lifestyle in this beautifully renovated single-story villa located in the highly sought-after 55+ waterfront community of Spanish Main Yacht Club. This move-in-ready 2-bedroom, 2-bath residence features a bright, open floor plan, brand-new appliances, updated finishes throughout, and a spacious Florida room perfect for relaxing or entertaining. Ideally situated just steps from the community marina, enjoy peaceful mornings watching manatees and dolphins while taking in breathtaking sunrise views over Sarasota Bay. Deeded private beach access to the Gulf of Mexico is just a short stroll away, offering unforgettable sunset walks along the sugar-sand beaches. Residents enjoy a maintenance-free lifestyle with exceptional amenities, including a heated community pool, clubhouse, library, shuffleboard courts, and marina with boat docks and kayak storage (subject to availability). An active social environment makes Spanish Main Yacht Club one of Longboat Key's most desirable waterfront communities. Conveniently located just minutes from the world-class shopping and dining of St. Armands Circle and the charm of Anna Maria Island, this villa is ideal as a year-round residence, seasonal getaway, or investment opportunity. Don't miss your chance to own a slice of paradise on Longboat Key.

683 Spanish Drive S Unit 214, Longboat Key
$950,000
3 Beds ⋅ 3 Baths ⋅ Harbour Oaks SubDv.
Move right in and start enjoying the Longboat Key lifestyle! Perfectly positioned behind the gates of highly sought after Bay Isles, this beautifully renovated residence combines elegant updates, low-maintenance living, and one of the area's most desirable resort-style communities. Every major improvement has already been completed, allowing you to simply unpack and begin enjoying paradise. The thoughtfully redesigned kitchen is the heart of the home, featuring all-new appliances, a wine refrigerator, custom all-wood cabinetry with convenient pull-out shelving, and an open design that flows effortlessly into the spacious living and dining areas. New tile flooring extends throughout the kitchen, living room, and primary suite, while new carpet creates warm, inviting guest bedrooms. The impressive list of recent upgrades provides exceptional peace of mind, including a new tile roof with hurricane-rated skylights, hurricane-impact windows and doors, new HVAC system with UV air purification lights, tankless water heater, water softener, new garage door opener, fresh interior paint throughout, and beautiful plantation shutters installed throughout the home. One of the home's most outstanding features is the enormous private screened lanai, creating an exceptional outdoor living space rarely found in this price range. Complete with an awning for covered grilling and tranquil pond views, this oversized outdoor retreat is perfect for morning coffee, afternoon relaxation, entertaining friends, or enjoying Florida's spectacular sunsets. A charming garden patio, accessible from both the guest bedroom and laundry room brings in the Florida sunlight and a place to grow tropical plants or a private herb garden. Ownership in Bay Isles includes exclusive access to the private Bay Isles Beach Club, where residents enjoy deeded Gulf-front beach access complete with gated parking, pavilions, picnic facilities, grills, restrooms, and miles of Longboat Key's world-famous white sand beaches. Flood insurance is conveniently included within the HOA fees, providing additional value and peace of mind. Just minutes away, the Longboat Key Moorings Marina offers deep-water boating accommodations, waterfront dining, and one of the Gulf Coast's premier marinas. Residents also have the opportunity to apply for membership at the renowned Longboat Key Club, featuring championship golf, world-class tennis and pickleball, resort pools, spa facilities, fitness centers, private beach amenities, and exceptional waterfront dining. Beyond the gates, enjoy the sophisticated coastal lifestyle that makes Longboat Key one of Florida's most sought-after destinations. Discover award-winning restaurants, waterfront dining, boutique shopping, art galleries, and charming cafés throughout Longboat Key, while nearby St. Armands Circle and Lido Key offer additional upscale shopping, fine dining, entertainment, and beach experiences just a short drive away. Downtown Sarasota's vibrant arts, theater, and cultural attractions are also conveniently close. Whether you're searching for a year-round residence, seasonal retreat, or luxurious lock-and-leave home, this extensively updated Bay Isles residence offers an exceptional combination of quality, comfort, location, and resort-style amenities that is truly difficult to match.

2350 Harbour Oaks Drive, Longboat Key
$395,000
2 Beds ⋅ 2 Baths ⋅ Twin Shores Mobile Home SubDv.
Pre-Construction. To be built. Welcome to PARADISE!!! Award winning beaches/sunsets on the Gulf side and a beautiful bay on the other. Sunrise to sunset this location can only make you smile. Enjoy the huge community heated pool and recently remodeled dockside clubhouse next to your brand new, 2026, elevated over 6 feet, 2-bedroom, 2 bath, open floorplan home. HURRY and you can help design your new home and deck. Bring your boat as you are only footsteps away from your own private marina. If you prefer the beach, go the opposite direction. You don't even have to worry about a chair. Twin Shores Beach and Marina have their own deeded entrance with brand new Tiki Hut and complimentary chairs to watch the sunset. All of this is located in the middle of Historic Longboat Key. Down the street, Bayfront Park has pickleball, tennis, basketball, playground, swings, picnic pavilions, big dog and little dog fenced parks with new turf, walking paths, kayak launch/storage and bathrooms. Go south and find your grocery and liquor store, banks, pharmacy and newly added large outdoor pavilion with bathrooms. Wonderful restaurants, shopping, golf, and fishing make island living incredible. See you soon!!! RUN, don't walk, paradise awaits! *** Lot #96 is also available and under construction. ***

71 Twin Shores Boulevard, Longboat Key
$4,300,000
4 Beds ⋅ 5 Baths ⋅ Country Club Shores SubDv.
Experience timeless coastal luxury in this exceptional custom estate, perfectly positioned in the prestigious Country Club Shores on the sought-after south end of Longboat Key. Constructed by renowned John Cannon Homes, this classical waterfront residence showcases the exceptional craftsmanship, architectural detail, and quality for which the builder is celebrated. Soaring ceilings, elegant millwork, walls of glass, and exquisite finishes create a light-filled home that perfectly frames the surrounding water views while offering nearly 4,400 square feet of beautifully designed living space. Ideally situated just one home from Sarasota Bay, this rare waterfront property captures sweeping bay views while providing the privacy, protection, and peace of mind that come with its prime location and newer construction. Beautifully updated in 2025 by Brista Homes, the residence features four bedrooms, five full baths, a spacious game room, and a generous loft office with breathtaking bay views—an inspiring space for working remotely or simply relaxing while enjoying spectacular sunsets. Multiple indoor and outdoor living areas are thoughtfully designed for effortless entertaining and everyday coastal living. Light-filled interiors blend refined custom details with relaxed elegance. The gourmet kitchen, appointed with newer appliances (2022), opens seamlessly to the living and dining areas, creating an inviting setting for intimate family gatherings or grand-scale entertaining. The luxurious primary suite is a private sanctuary featuring direct pool access, an elegant tray ceiling, and dual custom walk-in closets. Upstairs, guest suites offer en-suite baths and generous closets, providing exceptional privacy and comfort for family and visitors alike. Extensive recent improvements include a new roof (2025), updated windows, new balusters, and thoughtfully selected designer finishes throughout, creating a residence that perfectly balances timeless elegance with today's modern conveniences. Outdoor living is equally extraordinary. Expansive terraces, a sparkling pool, and tranquil waterfront views create the perfect backdrop for the coveted Florida lifestyle. For boating enthusiasts, the deep-water canal frontage features a composite dock, a 12,000-pound boat lift, and a newer seawall, providing immediate access to Sarasota Bay and just minutes to the Gulf of Mexico. Country Club Shores is one of Longboat Key's most prestigious waterfront communities, encompassing 19 picturesque streets with distinctive nautical and golf-inspired names. The homeowners association maintains the beautifully landscaped common areas and hosts a variety of neighborhood social events, fostering an exceptional sense of community. Residents enjoy convenient beach access and an unbeatable location just minutes from the world-class shopping and dining of St. Armands Circle, as well as the acclaimed restaurants, theaters, galleries, and cultural attractions of downtown Sarasota. Offering panoramic water views, exceptional boating, beach access,and an outstanding south Longboat Key location, this is a rare opportunity to own an extraordinary waterfront residence where timeless architecture, modern luxury, and the very best of Florida coastal living come together.

657 Halyard Lane, Longboat Key
$625,000
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv.
Simply magnificent! This beautifully renovated residence offers the perfect blend of sophisticated design, comfort, and effortless coastal living. Thoughtfully updated with designer finishes throughout, this move-in-ready home features an open, light-filled floor plan highlighted by floor-to-ceiling windows and a spectacular 38-foot covered terrace overlooking lush tropical gardens. Accessible from the living room and both bedrooms, the expansive terrace is the perfect place to enjoy your morning coffee, entertain guests, or relax with refreshing Gulf breezes. The updated kitchen flows seamlessly into the dining and living areas, creating an inviting space for everyday living and entertaining. Beautiful wood flooring, custom architectural details, stainless steel appliances, and abundant natural light add warmth and elegance throughout the home. The spacious primary suite serves as a private retreat with terrace access and a beautifully renovated ensuite bath featuring light wood cabinetry and granite countertops. The generous guest bedroom also opens to the terrace and includes a built-in Murphy bed, offering exceptional flexibility for visiting family and friends or a home office. Life at The Islander Club is truly resort-inspired. Residents enjoy over 400 feet of private Gulf-front beach, a heated beachfront swimming pool, a newly renovated state-of-the-art fitness center, two new sauna rooms, a Har-Tru® tennis court, two pickleball courts, a beautifully updated social room, library, secure key-fob entry, on-site management, and exceptional lock-and-leave convenience. Adding even greater value, The Islander Club has recently completed an extensive program of capital improvements, including exterior restoration and stucco repairs, balcony waterproofing, new roofs on both residential towers, clubhouse, and carports, modernized pool facilities with new tile, resurfacing, and equipment, refreshed landscaping and lighting, hurricane-rated windows and doors, and a completely renovated fitness center. These significant investments provide both peace of mind and long-term value for future owners. Whether you are searching for a full-time waterfront residence, a seasonal escape, or an exceptional investment opportunity, this beautifully updated condominium offers the very best of Longboat Key's coveted beachfront lifestyle.

2301 Gulf Of Mexico Drive Unit 44N, Longboat Key
$899,000
2 Beds ⋅ 2 Baths ⋅ Long Beach SubDv.
Discover this stunning, completely renovated interiors two-bedroom, two-bath home nestled in the Historic Longbeach Village on the quiet north end of Longboat key. More than just a home, this is a true coastal lifestyle. Perfectly positioned just a five minute walk to the largest public beach on Longboat Key. you'll enjoy effortless access to sugar-white sand, breathtaking Gulf sunsets, and endless days of beachside relaxation. Thoughtfully redesigned with upscale designer finishes throughout, this charming residence blends timeless Old Florida character with modern luxury. Terrazzo floors flow throughout the home, while the fully remodeled kitchen features premium cabinetry, quality appliances, and a functional layout that's perfect for everyday living or entertaining. Both bathrooms have been beautifully renovated with high-end finishes, including a luxurious primary bath with a large soaking tub, custom walk-in shower, and designer tile. No detail was overlooked and no expense was spared in this exceptional renovation. Leave the car behind and stroll to local favorites including Whitney's The Shore, and Mar Vista, all just minutes away. Ride your bike through the peaceful village, walk to the beach, or simply relax and enjoy the tranquil surroundings that make this neighborhood so special. Just over the bridge, Coquina Beach offers pristine shoreline, stunning Gulf Views, convenient concessions, and a popular farmers market, while Anna Maria Island provides an abundance of boutique shopping, waterfront dining, and laid-back island atmosphere. St. Armands Circle is only a short drive away with upscale shopping, restaurants, theater, marinas, and boat launches. Opportunities to own a fully renovated home in Historic Longbeach Village with this combination of location, walkability, and coastal charm are rare. Don't miss your chance to experience the serenity, beauty, and unmatched lifestyle of Longboat Key.

580 Linley Street, Longboat Key
$1,160,000
3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv.
Virtually Staged. On the 3rd floor of Building One, this 3-bedroom, 3.5-bath residence opens to one of Longboat Key's signature views: the fairways and lagoons of the golf course in the foreground and Sarasota Bay stretching to the horizon beyond. A semi-private elevator landing opens to 2,369 square feet centered on a great room, where floor-to-ceiling sliders frame the water and open to a wide covered terrace. The living room and owner's suite both capture the bay-and-golf view and open to this terrace, while a second terrace off the kitchen overlooks the treetops and serves the two guest bedrooms. The kitchen features a center island, double wall ovens, and a built-in refrigerator. The owner's suite includes a custom walk-in closet and a marble bath with glass shower, soaking tub, and dual vanities, and one guest bedroom is fitted with a built-in desk and shelving for an easy home office. Original and ready for your finishes, it is a rare chance to make a bayfront retreat your own. Two deeded parking spaces and a private storage unit complete the offering. Behind the gates of Bay Isles, Grand Bay offers two heated pools, Har-Tru tennis, a fitness center, clubhouse, on-site management, and 24-hour security. Owners also receive deeded access to the private Bay Isles Beach Club on the Gulf. St. Armands Circle, downtown Sarasota, Harbourside golf and marina, and the beaches of Lido and Siesta Key are all minutes away.

3060 Grand Bay Boulevard Unit 133, Longboat Key
$850,000
Conrad Beach SubDv.
"Create your ideal coastal retreat on the last available homesite in the peaceful and picturesque Conrad Beach enclave on Longboat Key. Just a 5-minute walk to the Gulf of Mexico and Whitney’s restaurant and a 2-minute drive to renowned restaurant Shore Longboat Key. This prime location offers easy access to pristine beaches and stunning sunsets. Conrad Beach is an award-winning neighborhood esteemed for its coastal charm and beautiful homes with low association fees covering yard maintenance, irrigation, and a community pool for a carefree lifestyle. Spanning 9,757 square feet, this homesite provides ample space to design your dream home and is conveniently located steps away from the community pool, offering a perfect retreat on sunny days. Longboat Key boasts some of Florida's most sought-after beaches, restaurants, tennis courts, and waterfront parks. With easy access to downtown Sarasota and St. Armands Circle, you'll have endless opportunities for recreation and entertainment. Don't miss this opportunity to create your coastal masterpiece in one of Florida's most desirable locations, where sun, sand, and sea await."

363 Firehouse Lane, Longboat Key
$499,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv.
Welcome to 578 Spanish Drive S, a completely renovated 2 bedroom, 2 bathroom villa in Spanish Main Yacht Club on Longboat Key. Renovated completely with thoughtful attention to detail, this move-in ready residence showcases high-quality modern finishes while providing access & amenities to one of Longboat Key's established waterfront communities with a deepwater marina and deeded beach access. The redesigned interior features an open kitchen centered around a quartz waterfall edge island, soft close cabinetry, with all new stainless-steel appliances, including a wine refrigerator and a refrigerator with a built-in craft ice maker. Luxury vinyl plank flooring extends throughout the home, complemented by a smart thermostat for everyday convenience. Every room reflects the comprehensive renovation, and the home is further enhanced by a 2012 tile roof, new PGT hurricane impact windows, and sliding glass doors that open to a private paver patio overlooking a wooded landscaped setting. Spanish Main Yacht Club offers private deeded beach access to the Gulf of Mexico, a heated community pool, clubhouse, shuffleboard courts, and a pet-friendly environment. The community’s deepwater marina offers approximately 40 boat slips available for lease, accommodating vessels up to 40 feet with water and electric service, while providing direct boating access from Sarasota Bay to the Gulf of Mexico. Residents also enjoy opportunities for fishing, kayaking, paddleboarding, and other waterfront recreation. Located near Publix, St. Armands Circle, downtown Sarasota, shopping, dining, cultural attractions, botanical gardens, Anna Maria Island, and Sarasota-Bradenton International Airport, this extensively renovated villa offers an exceptional combination of updated interior finishes, outdoor living, boating amenities, and convenient access to the best of Longboat Key and the surrounding Sarasota area. Please see attached document for the full list of renovations & upgrades and full walkthrough video and virtual walkthrough. Not required to be 55 to purchase.

578 Spanish Drive S, Longboat Key
$625,000
2 Beds ⋅ 2 Baths ⋅ Islander Club Of Longboat SubDv.
Experience exceptional Gulf-front living in this beautifully maintained two-bedroom, two-bath residence at the highly desirable Islander Club on Longboat Key. Enjoy peaceful views of the manicured grounds, entrance, and tennis courts from the expansive wraparound terrace offering more than 60 feet of private outdoor living space—perfect for relaxing or entertaining. Inside, the light-filled open floor plan features floor-to-ceiling sliding glass doors, a well-appointed kitchen with KitchenAid appliances, and spacious living and dining areas. The primary suite offers terrace access and an en-suite bath, while the guest bedroom provides comfortable accommodations for visitors or a home office. Recent updates include hurricane-impact windows and doors, a Bosch HVAC (2016), water heater (2020), in-unit humidistat, assigned parking, and extensive community improvements including new elevators, roof, porte cochère, fitness center, clubhouse, locker rooms with saunas, recreation room, and landscaping. End-window replacements have also been ordered. The Islander Club offers over 400 feet of private Gulf beach frontage, a heated beachfront pool, fitness center, Har-Tru tennis court, two pickleball courts, two fishing piers, on-site management, and 24/7 maintenance staff. Just minutes from St. Armands Circle and Downtown Sarasota, this is your opportunity to enjoy the very best of Longboat Key beachfront living.

2301 Gulf Of Mexico Drive Unit 45N, Longboat Key
$550,000
2 Beds ⋅ 2 Baths ⋅ Banyan Bay SubDv.
Move-in-ready condition, ground-floor bayside condominium with Sarasota Bay views and deeded private Gulf beach access in the sought-after Banyan Bay Club! Discover effortless coastal living in this beautifully updated 2-bedroom, 2-bath residence offering 1,155 square feet on the bayside of Longboat Key. Thoughtfully renovated throughout, this inviting home features new luxury vinyl plank flooring, new kitchen appliances, updated bathrooms with new vanities, and a bright, open floor plan designed for comfortable island living. Enjoy Sarasota Bay views from the living room, primary bedroom, and private rear patio. Step directly from your patio onto the beautifully landscaped lawn, where you can enjoy your morning coffee, watch boats and dolphins pass by, observe abundant coastal wildlife, and welcome beautiful Florida sunrises. The convenient ground-floor location offers effortless access and seamlessly blends indoor and outdoor living. Residents of this pet-friendly community enjoy the best of both worlds with deeded private Gulf beach access and outstanding amenities, including a heated pool, clubhouse, pickleball, tennis, fishing pier, kayak storage and launch, and assigned parking. Whether you enjoy boating, kayaking, fishing, shelling, or relaxing on the beach, this community offers the quintessential Longboat Key lifestyle. Ideally located near championship golf, waterfront dining, marinas, boutique shopping, St. Armand's Circle, and downtown Sarasota, this exceptional residence is perfect as a primary home, seasonal retreat, or investment opportunity. Don't miss this rare opportunity to own an updated, move-in-ready, bayside condominium with Sarasota Bay views, deeded private Gulf beach access, and the relaxed elegance of island living. EASY TO SHOW. SUPRA ON storeroom door across from front door.

5260 Gulf Of Mexico Drive Unit 413, Longboat Key
$495,000
2 Beds ⋅ 2 Baths ⋅ Seaplace SubDv.
Seaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & umbrellas provided on private beach portion. Elegant turnkey-furnished unit with hurricane impact doors & windows. Next to clubhouse pool, gym, sauna & community kitchen. Two properties from St. Regis Resort restaurants & beach bar.

1945 Gulf Of Mexico Drive Unit M2-402, Longboat Key
$325,000
1 Beds ⋅ 1 Baths ⋅ Neptune On Longboat Key SubDv.
Coastal Living on Longboat Key – Neptune Condominium Welcome to your island retreat at Neptune on Longboat Key, a charming boutique community just moments from the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect blend of comfort, style, and an unbeatable Longboat Key lifestyle. Step inside to discover a bright, open floor plan featuring luxury vinyl flooring, coastal-inspired décor, crown molding, and a tastefully renovated kitchen with cabinetry, updated appliances, quartz-look countertops, and a deep stainless sink. The spacious living and dining area flows effortlessly onto a screened lanai where you can relax with a morning coffee. The generous bedroom provides a peaceful retreat with abundant natural light, while the updated bath and thoughtful finishes create a move-in-ready coastal escape. Located on the desirable south end of Longboat Key, Neptune is a small boutique community known for its quiet atmosphere and convenient location. You're just a short stroll to the beach and only minutes from St. Armands Circle, where you'll enjoy world-class dining, shopping, and entertainment. Downtown Sarasota, cultural attractions, golf, boating, and marinas are also just a short drive away. Neptune is a small, low-density community with minimal common amenities, helping keep ownership simple while offering a peaceful island setting. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this turnkey-furnished condo offers an exceptional opportunity to own a piece of paradise on Longboat Key.

2850 Gulf Of Mexico Drive Unit 4, Longboat Key
$599,900
2 Beds ⋅ 3 Baths ⋅ Cedars East SubDv.
Turn-Key Furnished Waterfront Townhome in Cedars East on Longboat Key! Beautifully updated 2-bedroom, 2.5-bath residence featuring tranquil water views, an expanded open floor plan, and an updated kitchen with shaker cabinetry, granite countertops, and stainless steel appliances. Offered fully furnished and move-in ready, it's ideal as a primary residence, seasonal retreat, vacation home, or investment property. Cedars East offers resort-style amenities including a heated junior Olympic pool, Har-Tru tennis courts, pickleball, fitness center, clubhouse, fishing pier, kayak launch, mangrove boardwalks, restaurant, and tiki bar. (Pool membership included. Some amenities require optional club membership.) Located just minutes from Longboat Key beaches, St. Armands Circle, Anna Maria Island, waterfront dining, shopping, golf, and downtown Sarasota, this is an outstanding opportunity to own in one of Longboat Key's premier waterfront communities. Buyer shall independently verify all room dimensions, association rules, membership requirements, rental restrictions, and all information deemed material.

848 Evergreen Way, Longboat Key
$479,000
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv.
Welcome to Longboat Harbour D-204, a beautifully maintained second-floor condominium in one of Longboat Key's most desirable gated waterfront communities. Ideally located in Building D—the closest building to the community's private Gulf beach access—this residence offers umatched convenience to the beach pavilion, showers, restrooms, and private beach lockers. Inside, you'll find a bright and comfortable floor plan featuring granite countertops, an in-unit washer and dryer, a spacious bedroom with a new impact window, and electric blinds. Additional highlights include a private storage locker, covered carport parking space, proximity to the elevator, a new roof, and all assessments fully paid. Longboat Harbour offers resort-style amenities including four heated swimming pools, a fitness center with sauna, tennis and pickleball courts, art studios, a woodworking shop, and a yacht club with a protected harbor. Located just miles from St. Armands, Lido Beach, Downtown Sarasota, Anna Maria Island, Homes Beach, and Bradenton Beach, this is the perfect opportunity to enjoy the best of Longboat Key waterfront and beach living.

4340 Falmouth Drive Unit D-204, Longboat Key
$569,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv.
If you are looking for a tastefully upgraded Longboat Key beach house, this is it! Relax in your completely renovated coastal-contemporary, stand-alone villa, with its front pond view, private rear patio and large yard space. The uncrowded, 11-mile Longboat Key beach is directly across Gulf of Mexico Drive via Spanish Main's private deeded access. Your spacious, light-filled home welcomes you with a charming entrance foyer, open living-dining room with built-in cabinets and a large kitchen-family room area with sliding doors to the rear yard. Your bright kitchen has an island, new appliances, quartz counters, and wood cabinets with lots of storage space. Important additional benefits include a new electric hot water tank, new hurricane rated doors and rear sliders, tile roof replaced in 2017, flat roof in 2024, impact windows in 2020 and 2024, and A/C in 2022. The primary bedroom has a walk-in closet and an en suite bath with a new walk-in shower and vanity. The guest bedroom has a view of the pond and double closets. The guest bathroom has a skylight and a new walk-in shower, vanity, linen and medicine cabinets. If you want to move right in or rent it, the attractive turn-key furnishings are negotiable. Outside, there is a large side storage area for bicycles and beach toys. The front porch offers a tranquil area to relax and view the large pond with its ducks, jumping fish, and pretty night lights. Walk, bike or drive to the heated community pool, patio area, and clubhouse adjacent to the deep water marina and kayak launch. If you are a boat person, slips can be rented, as available, for an extremely reasonable cost and there is easy access to Sarasota bay and the Intracoastal Waterway with no fixed bridges. Spanish Main Yacht Club is an over-55 community, conveniently located near several restaurants, Durante Park, community tennis, pickle-ball, dog park, fitness activities and St. Armands Circle shops and restaurants. Let me show you the lifestyle that this beautiful, unique villa has to offer.

524 Spanish Drive S Unit 125, Longboat Key
$400,000
Longboat Key Moorings SubDv.
Stunning Sarasota Bay Views! An easy access slip with the views to go along with the superb amenity package, Slip R-13 at Longboat Key Club Moorings Marina provides one of the most desired locations as a Yacht Club Member slip in the Marina. With the slip measuring 80 x 23.5, and a usable beam of 19 feet and extra wide finger pier. This is a desired 'inside the T-head' slip location. The Longboat Key Club Moorings Marina is a World Class deep water marina providing direct access to Sarasota Bay and ICW. Yacht Club membership at the Longboat Key Club Moorings provides members access to the private clubhouse, which is well appointed with TV, conference room, private pool area, outside seating and tables, grill, and bathhouse all in a relaxing atmosphere. Additionally, the Longboat Key Club offers multiple restaurants, world class tennis, pickleball and golf facilities, fitness center, with spa and beach access. The Marina is also located within close proximity to Publix, CVS, and world class shopping at St. Armand's Circle. The longest vessel this slip will accommodate is 75 feet. Beam depends on the vessel type and measure. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit R-13, Longboat Key
$307,000
1 Beds ⋅ 1 Baths ⋅ Longboat Harbour Towers SubDv.
PRICE IMPROVED — WATERFRONT VALUE ON LONGBOAT KEY! Beautifully furnished 1-bedroom waterfront condo in a gated, active boating community, ideally suited as a seasonal retreat, second home, or rental opportunity. Private deeded beach access with gated parking, beach-chair storage, indoor showers/facilities, and picnic area is a standout amenity. Enjoy a true resort-style lifestyle with 4 heated pools, fitness center, tennis, pickleball, kayak and bicycle storage, banquet hall, and first-come, first-served boat slips. The enclosed lanai provides additional living space, while over $$ in hurricane-impact sliding glass doors and windows offers abundant natural light, comfort, and peace of mind. Price improved and ready for the upcoming season! Move in, enjoy the Longboat Key lifestyle, and explore seasonal rental potential. Waterfront + private beach + boating + resort amenities at an improved price. Bring your offer—this one is ready to be enjoyed!

4350 Chatham Drive Unit 105, Longboat Key
$649,000
2 Beds ⋅ 2 Baths ⋅ Pelican Harbour & Beach Club SubDv.
COMMUNITY BOAT SLIP AVAILABLE! It really is all about the location- and of course the view! Situated on gorgeous Sarasota Bay, this lovely two bedroom, two bath first floor condo offers a walk out to the sculpted grounds of Pelican Harbour and great water views of the bay from your private screened lanai. Recently professionally renovated in tasteful coastal chic, this beautifully updated condo boasts new hurricane impact windows, designer Samsung kitchen appliances, ceramic tile flooring, an island kitchen with granite countertops and white shaker wood cabinets, ceiling fans, plantation shutters, closet built-ins, washer and dryer, and new window treatments. New AC (2025). Pelican Harbour and Beach Club is a pet friendly community and offers world class amenities including private gulf beach access, a heated resort-style pool, kayak and bike storage, day dock, tennis, and pickleball. This well-maintained community has successfully completed its milestone inspection, has fully-funded reserves, and has no special assessments. Association fees include building maintenance, landscaping, building insurance, cable, water, sewer, trash, professional management, and pest control. The community has covered reserved carports, new roofs and a composite day dock that is perfect to enjoy a cup of coffee while catching those stunning Florida sunrises over water. At this writing, community has two 30 ft boat slips available at $600 per year. Pelican Harbour is centrally located mid key, with convenient access to St. Armands Circle, Bayfront Park, Publix, and fine dining at a number of outstanding restaurants. Your unique opportunity to enjoy the Longboat Key lifestyle awaits!

4234 Gulf Of Mexico Drive Unit M1, Longboat Key
$479,500
Longboat Key Moorings SubDv.
Club membership is NOT required and Owner Financing IS available for this rare 72' x 21' deep water boat slip on C-Dock at Longboat Key Moorings Marina, allowing for a 67' x 19' boat. Enjoy a premier deep-water, storm-protected marina location with direct access to Sarasota Bay, the ICW, and the Gulf. Longboat Key Moorings offers full-service amenities including dock crew, harbor concierge, 24-hour manned guard gate, cable TV, electricity, water, Wi-Fi, on-site fuel, pump-out service, and repair/maintenance services. Ideally located just minutes from St. Armands Circle, downtown Sarasota, Bradenton Beach, waterfront dining, shopping, and world-class boating. While membership to the Longboat Key Club is optional, it is not required to own this slip. A rare opportunity to secure premium waterfront access in one of Florida's most desirable boating communities.

2600 Harbourside Drive Unit C11, Longboat Key
$310,000
1 Beds ⋅ 1 Baths ⋅ Gulfshore Of Longboat Key SubDv.
BEAUTIFULLY REMODELED: This home is the epitome of simple elegance with a bit of modern flair. It has been remodeled to create a home that is very open and full of light. It features a large Living Room with a wall-mounted TV and a fireplace; a kitchen that has all new cabinets and granite counter tops; a Primary bedroom, with a small attached room that could easily be converted to a small bedroom. The full Bath features a step-in shower. In addition, there is an outside bath house, that has been totally remodeled, and has a toilet, sink and shower that is perfect for when you return from the beach. Gulfshore of Longboat Key is located on a perfect parcel of land. It has it all – approximately 450-500 feet of private access to a pristine sand beach on the turquoise waters of the Gulf of Mexico, a marina on Sarasota Bay, large community heated pool, remodeled clubhouse with a commercial kitchen, and a well-maintained and managed campus. Gulfshore is proud of their financial management and the very affordable cost of living that has resulted. Truly, Gulfshore is a remnant of Old Florida that is just six miles from the world-famous St. Armand’s Circle. St. Armand’s has a plethora of great restaurants and world-class shopping. Gulfshore does not permit rentals or pets and it is a 55+ community. Please call now to schedule your personal showing and to view your future home and live the Florida dream.

3710 Gulf Of Mexico Drive Unit E22, Longboat Key
$1,995,000
3 Beds ⋅ 4 Baths ⋅ Marina Bay SubDv.
Welcome home to this corner 3 bed/3.5 residence with sweeping southeast bay and city views at Marina Bay behind the Bay Isles gates on Longboat Key. This showstopping residence has been recently renovated with designer inspired flooring, fixtures and thoughtful details throughout. The kitchen and dining rooms are positioned to capture direct views of Sarasota Bay while offering every convenience including a full wet bar area with wine refrigeration, custom cabinetry, breakfast bar, cabinet pantry and large laundry room with another closet pantry. The expansive living area features incredible wall space for works of art with natural light from the floor to ceiling sliders surrounding the wraparound screen terrace which frames the city skyline and Sarasota Bay. The primary suite has its own private wing and boasts a large shower with multiple shower heads, floating vanity, designer stone tilework, two large walk-in closets and a peaceful bedroom sanctuary with access to the west terrace and tranquil sunset skies. Both guest bedrooms are ensuite with ample closet space (one walk-in and one built-in) and recently renovated bathrooms. Other highlights include hurricane shutters, plantation shutters, automatic shades in the main living area, an under-building parking space, semi-private elevator and membership to the Bay Isles Beach Club on the Gulf. The Beach Club is a private, gated retreat for Bay Isles residents offering a large outdoor pavilion, tropical cabanas, grills and picnic facilities, private showers and restrooms. Marina Bay is a pet friendly community with on-site management, heated pool & spa, gas grill area, fitness room, tennis and pickleball courts. Located nearby the Longboat Key Club Marina, Publix, CVS, Post Office and minutes from St Armands and the cultural hub of downtown Sarasota. Get ready to start your Longboat Life today!

2450 Harbourside Drive Unit 244, Longboat Key
$1,375,000
3 Beds ⋅ 3 Baths ⋅ Longboat Shores SubDv.
Expect luxury living and a world of conveniences within the serene enclave of Buttonwood Harbour on Longboat Key, where care and impeccable style converge in this 3BR/3BA tropical oasis. As you approach, the vast circular paver drive, embraced by lush, professionally maintained landscape, sets the stage for what awaits beyond the architecturally pleasing covered front entryway. Step inside to discover the attention to detail that defines this updated home, as gorgeous new tile floors throughout grace and harmonize with neutral tones and exquisite touches, including stately plantation shutters adorning every window. The flowing floor plan effortlessly guides you to the expansive pool area, blending indoor elegance with outdoor convenience. The beautifully remodeled kitchen is both stylish and functional, seamlessly connected to the living room, and featuring a large breakfast Island, tile backsplash, a wine refrigerator, and Bosch appliances. Relax in the cozy Florida room, which offers a tranquil retreat with walls of sliders that blur the boundaries between indoor and outdoor living. Outside, the sparkling heated pool beckons, surrounded by ample space on the lanai for entertaining or simply basking in the tropical ambiance. The expansive primary suite is a sanctuary of comfort, with slider access to the pool area, new tile flooring, and a remodeled primary bath boasting dual vanities and a glass-enclosed walk-in shower adorned with stunning tilework. Equally inviting, the two guest accommodations offer spacious comfort, with elegantly remodeled bathrooms. Set in a prized mid-key location, Buttonwood Harbour offers residents a short walk to the beach and a community Harbor with boat slips available to lease.

602 Buttonwood Drive, Longboat Key
$915,000
3 Beds ⋅ 2 Baths ⋅ Sands Point SubDv.
Don’t miss this rare opportunity to call Sands Point home – an iconic beachfront community widely regarded as the crown jewel of Longboat Key. Nestled on the island’s coveted southernmost tip, this move-in-ready residence offers breathtaking sunsets and an unparalleled coastal lifestyle. Offered at an attractive value, this coastal escape presents a rare opportunity for the new owner to add their own finishing touches and create a truly personalized retreat. Welcome to your slice of paradise, where every day feels like a five-star coastal retreat, nestled inside the gates of the Longboat Key Club. Gracefully framed by towering palms, the curved waterfront drive creates a memorable sense of arrival, setting the tone for this one-of-a-kind mid-century modern residence where coastal elegance and timeless design converge. This spacious 1941 square feet, with its open floor plan feels more like a home than a condo. Step inside this bright third floor residence and discover a two bedroom, an office staged as a 3rd. bedroom and two baths, set in a split plan for privacy. Thoughtfully designed with warm custom cabinetry, elegant stone-inspired surfaces, and contemporary stainless appliances, this kitchen combines timeless craftsmanship with effortless coastal living. Floor to ceiling expanses of glass span the living area, offering a panoramic garden view and bathing the room in sunshine. The oversized layout provides endless possibilities for entertaining, gathering or simply enjoying the peaceful surroundings. Community amenities abound – enjoy the private beach with tiki’s, lounge chairs, pool, spa, library, community room w/ kitchen, marina access, bicycle storage, kayak launch, and additional owner’s storage space. Within walking distance to the well-renowned St Armands Circle for shopping and dining experiences. The pristine white sandy beach and gentle turquoise waters are calling your name. Schedule your private showing today and discover the lifestyle you deserve.

100 Sands Point Road Unit 303, Longboat Key
$339,000
1 Beds ⋅ 1 Baths ⋅ Beach Harbor Club SubDv.
Welcome to coastal living at its finest in this beautifully renovated 1-bedroom, 1-bath condo at Beach Harbor Club on coveted Longboat Key. Perfectly positioned adjacent to the beach, this second-story retreat offers a peek-a-boo view of the sparkling Gulf and 761 square feet of stylish, light-filled comfort. Step inside to discover a fully updated interior featuring impact windows, a new AC system, and modern finishes throughout. Every detail has been thoughtfully considered to deliver effortless island living. The building offers convenient elevator access, plus a wealth of amenities designed for relaxation and recreation. This vibrant community stretches from beach to bay, granting you deeded beach access and a rooftop deck where unforgettable sunsets await. Cool off in the heated pool, unwind at the tiki bar, or gather with neighbors in the clubhouse. Outdoor enthusiasts will love the kayak and canoe launch, while boat slips are available first-come, first-serve for $700/year. Additional perks include a fitness center, laundry facility, bike storage, storage locker, wood shop, and on-site management. Condo fees thoughtfully cover TV, internet, and water for added peace of mind. Beyond your doorstep, indulge in the best of the region. Savor waterfront dining at Dry Dock Waterfront Grill, shop at nearby Publix, or explore the boutiques of St. Armands Circle. Anna Maria Island's charm is just a short drive away. Discover your slice of paradise—schedule your private showing today and embrace the Longboat Key lifestyle.

3804 Gulf Of Mexico Drive Unit B204, Longboat Key
$4,395,000
6 Beds ⋅ 6 Baths ⋅ Longboat Shores SubDv.
Private Marina. Experience the pinnacle of coastal living in this exceptional new construction waterfront residence, ideally situated in the heart of Longboat Key. Perfectly positioned across from the community marina with direct boating access to the Gulf of Mexico, this move-in-ready home offers an extraordinary blend of modern elegance, superior craftsmanship, and the relaxed sophistication of island life. Spanning 4,106 square feet, this thoughtfully designed residence features 5 spacious bedrooms, a private office/den, and 4 luxurious bathrooms, creating an ideal setting for both everyday living and entertaining. Finished floor elevation above base flood elevation, the home provides added peace of mind while maximizing its commanding presence. Designed to embrace Florida’s indoor-outdoor lifestyle, expansive sliding glass doors seamlessly connect the interior living spaces to two generous covered lanais, overlooking a resort-style heated pool and spa. Whether hosting sunset gatherings or enjoying a quiet morning overlooking the water, every space has been crafted to capture the beauty and serenity of waterfront living. Inside, quality finishes and attention to detail abound. Wide-plank engineered hardwood flooring flows throughout the home, complemented by designer quartz countertops, custom cabinetry, and an open-concept floor plan filled with natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring an oversized island, premium finishes, and a spacious walk-in pantry. The convenience of dual laundry rooms further enhances the home's thoughtful design. For boating enthusiasts, the property features a concrete seawall and marina access, offering quick and convenient access to Sarasota Bay and the Gulf waters beyond—making it easy to enjoy world-class fishing, waterfront dining, and unforgettable days on the water. A boat slip is currently leased by the owner. Tucked away on a quiet street, yet just moments from Longboat Key’s pristine beautiful sand beaches, championship golf courses, marinas, boutique shopping, and renowned dining destinations, this residence delivers the perfect balance of privacy and accessibility. Offering the rare combination of new construction, waterfront location, elevated construction, luxury finishes, and Gulf boating access, 626 Buttonwood Drive represents an exceptional opportunity to own a premier Longboat Key waterfront retreat in one of Florida’s most coveted coastal communities. Luxury. Boating. Beach Life. Welcome Home.

626 Buttonwood Drive, Longboat Key
$2,795,000
4 Beds ⋅ 4 Baths ⋅ Shipmans Add SubDv.
Tucked away on the coveted north end of Longboat Key, this custom-designed coastal contemporary residence offers a rare blend of modern architecture, boating access, and waterfront living. Designed by architect Mark Sultana of DSDG, the home was completed in 2011. Positioned along a protected saltwater canal with private dockage and just moments from the Gulf's sandy shoreline, this island retreat captures tranquil water views, tropical surroundings, and spectacular sunsets from multiple levels. Spanning nearly 3,100 square feet, the four-bedroom layout is designed for effortless indoor-outdoor living. The main level serves as the heart of the home, where soaring 18-foot whitewashed cypress ceilings crown the open great room. A contemporary gas fireplace with gray glass tile anchors the living area, while walls of impact-rated glass fill the residence with natural light and frame views of the canal and lush mangroves beyond. The open-concept design seamlessly connects the living room, dining area, and gourmet kitchen, creating an ideal environment for both entertaining and everyday enjoyment. The chef's kitchen is appointed with custom solid-wood cabinetry by Campbell Designs, quartz countertops, glass tile backsplash, breakfast bar, oversized pantry, water filtration, and premium appliances. Thoughtful details such as Lutron lighting system, built-in audio throughout the interior and exterior, impact-rated doors and windows, soft-close drawers, metal barrel roof, propane-fueled pool heater and outdoor grill, oversized two-car garage with workshop, abundant storage, and dedicated kayak storage enhance both function and style. An open staircase crafted from powder-coated aluminum with blonde maple treads creates an architectural focal point while connecting the living spaces. The second level is devoted to private accommodations, including two guest bedrooms sharing a beautifully appointed bath, with one currently configured as a den. The upper floor is highlighted by the primary suite featuring dual walk-in closets, a private waterfront terrace, and spa-inspired bath with freestanding soaking tub, marble-topped dual vanity, oversized glass shower, and separate water closet. Adding exceptional flexibility, a detached cabana suite overlooks the pool deck and serves as a private guest retreat. Complete with a full bath, walk-in closet, morning kitchen, and separate entrance, this space functions perfectly as a fourth bedroom, guest quarters, home office, or artist's studio. Outdoor living is equally impressive. White terrazzo terraces on each floor overlook the 36-foot lap pool and spa with waterfall feature, creating a private tropical setting enhanced extensive landscape lighting, mature exotic foliage, and lush zoysia grass. The private IPE wood dock includes an 8,000-pound lift, kayak launch, water and electric service, and underwater lighting for boating enthusiasts. Located on one of Longboat Key's most desirable stretches, residents enjoy deeded access to the island's pristine Gulf beach just across the street, waterfront dining, marinas, and scenic biking paths. The Longboat Key Club's golf and tennis facilities are nearby, while St. Armands Circle offers boutique shopping and acclaimed restaurants just minutes away. Downtown Sarasota's cultural attractions are easily accessible, creating an exceptional coastal lifestyle that blends privacy, recreation, and convenience.

705 Jungle Queen Way, Longboat Key