Longboat Key Homes with Sailboat Water Water Frontage

Longboat Key Homes with Sailboat Water Water Frontage

Welcome to Longboat Key, Florida – a hidden gem nestled along the stunning Gulf Coast. This picturesque barrier island is renowned for its pristine beaches, lush tropical landscapes, and a vibrant community that embraces the best of coastal living. With its charming blend of luxury and laid-back charm, Longboat Key offers an idyllic escape for those seeking a tranquil lifestyle amidst the beauty of nature.

One of the most alluring features of Longboat Key is its spectacular homes with sailboat water frontage. Imagine waking up each morning to the gentle sounds of the waves lapping against your dock, with direct access to the open waters of the Gulf of Mexico. These exquisite properties provide not just a home, but a lifestyle defined by adventure and relaxation. Whether you’re an avid sailor or simply enjoy the serenity of waterfront living, these homes offer an unparalleled experience.

The sailboat water frontage ensures that you can embark on spontaneous outings, explore nearby islands, or enjoy a sunset cruise at your leisure. With a variety of architectural styles and modern amenities, these homes cater to diverse tastes and preferences, making it easy to find your perfect sanctuary.

Longboat Key also boasts a rich array of dining, shopping, and recreational opportunities, from upscale restaurants to charming boutiques. Whether you’re lounging on the beach, playing a round of golf, or indulging in a spa day, this vibrant community has something for everyone.

Discover the enchanting allure of Longboat Key and experience the ultimate in waterfront living. Your dream home awaits!

Newest Longboat Key Homes with Sailboat Water Water Frontage

$6,995,000
4 Beds ⋅ 5 Baths ⋅ Lighthouse Point SubDv. ⋅ 34228 Zip Code
Some homes are simply built differently. Conceived as a grand private waterfront estate, this remarkable residence within the exclusive gated enclave of Lighthouse Point is a rare expression of architectural elegance, exceptional privacy, world-class boating, and effortless coastal luxury. Perfectly positioned on more than one-third of an acre overlooking a tranquil lagoon with coveted bridgeless access to Sarasota Bay and the Gulf of Mexico, this extraordinary four-bedroom, four-full-bath, one-half-bath residence unfolds across nearly five thousand square feet of refined living space. Originally conceived as a grand coastal estate and extensively reimagined in 2021, the home creates an atmosphere that is both elegant and remarkably livable. A dramatic two-story foyer with soaring tongue-and-groove ceilings, arched French doors, custom millwork, and an architectural wraparound gallery immediately establishes a while walls of glass frame shimmering water views and expansive sliding doors seamlessly connect the interior living spaces to spectacular waterfront terraces. Designed for both intimate gatherings and grand entertaining, the elegant great room flows effortlessly to the resort-inspired outdoor living areas overlooking the saltwater pool, spa, lush tropical landscaping, and private dock beyond. At the heart of the home, the custom Cucina Ricci kitchen is as beautiful as it is functional, featuring handcrafted cabinetry, an oversized entertaining island, and an exceptional suite of integrated Miele VitroLine appliances, including double ovens, induction cooking, and a built-in coffee system. Just beyond, a waterfront lounge offers the perfect setting for casual living or media enjoyment while maintaining an uninterrupted connection to the outdoor loggia. Privately situated on the main level, the owner's retreat is a true sanctuary, offering peaceful water views, direct terrace access, dual custom walk-in closets, and a beautifully renovated spa-inspired bath with oversized vanities, designer finishes, and an expansive walk-in rain shower. Upstairs, three spacious en-suite guest bedrooms and an additional loft-style lounge or office provide luxurious accommodations for family and guests. Outside, the estate lives like a private waterfront resort, where a stunning travertine pool terrace, mature tropical landscaping, integrated landscape lighting, and multiple outdoor entertaining areas create an extraordinary setting for year-round coastal living. Boating enthusiasts will appreciate the protected deep-water dock featuring a fourteen-thousand-pound lift, upgraded motors, dockside Wi-Fi, and immediate bridge-free access to Sarasota Bay and the Gulf, placing some of Florida's finest boating just moments from your backyard. Thoughtfully appointed throughout, the residence also features a fully renovated interior, impact-rated windows and doors, hurricane protection, a whole-house Kohler generator, integrated Yamaha indoor/outdoor audio, a spacious three-car garage with EV charging capability, and numerous additional upgrades that allow the home to be enjoyed with complete confidence. Residents of Lighthouse Point enjoy private tennis courts, a short stroll to the pristine beaches of Longboat Key, and convenient access to the Longboat Key Club, St. Armands Circle, and the world-class dining, shopping, and cultural attractions of downtown Sarasota. An exceptional offering in one of Longboat Key's most prestigious waterfront communities.

65 Lighthouse Point Drive, Longboat Key
$689,000
2 Beds ⋅ 2 Baths ⋅ Longboat Key SubDv. ⋅ 34228 Zip Code
Turnkey-Furnished Longboat Key Condo with Dock Access & Rental Potential. Discover effortless coastal living in this beautifully furnished turnkey condo on desirable Longboat Key. Enjoy rare short-term rental flexibility, a bright and stylish interior, and immediate move-in or income potential. Relax by the waterfront dock that is perfect for sunsets and kayaking. Enjoy close access to Gulf beaches, dining, shopping, and island amenities. An ideal Longboat Key vacation retreat or rental investment.

5310 Gulf Of Mexico Drive Unit 16, Longboat Key
$725,000
2 Beds ⋅ 2 Baths ⋅ Bay Harbour Apts SubDv. ⋅ 34228 Zip Code
Location! Location! Location! Awesome, Spectacular Bay views from the kitchen, dining room, living room and primary bedroom! One Bridge to the Gulf! No wait list boat slip! Longboat Key is the place you want to be for the quiet solitude of a gulf front key condo with easy access to the culture and services of Sarasota! This two bedroom, two bathroom Condo in the bay side community of Bay Harbour, has its own private marina with no wait list, and is just one bridge to the Gulf! Beach access is within minutes from several locations on Longboat, Lido and Anna Maria Island. With a Base Flood Elevation of 10 Ft, this unit was High and Dry during the storms of 2024. It has been exquisitely redesigned with upscale quartz and Cambria counter tops, ceramic and porcelain tile flooring and Bosch Appliances. There is plenty of storage available with the pantry and built in closets. Bay Harbour is a South Longboat Key community of 39 units in two buildings with a private pool, easily accessible pool baths, community room and fitness center. Each unit has assigned carport parking and separate storage. A well-managed and well-maintained community with reserves; the condo fees are among the lowest on the gulf!

448 Gulf Of Mexico Drive Unit A104, Longboat Key
$499,900
2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code
Welcome to your slice of paradise on beautiful Longboat Key. Priced to sell and offered fully furnished, this beautifully maintained two-bedroom condominium is truly move-in ready. Combining breathtaking Sarasota Bay views with exclusive deeded beach access, this exceptional residence offers the perfect blend of waterfront serenity, resort-style amenities, and effortless coastal living. Wake each morning to spectacular sunrises over Sarasota Bay as dolphins, manatees, and coastal birds provide an ever-changing natural backdrop from your enclosed lanai. Inside, you’ll find a move-in-ready residence featuring granite countertops, plantation shutters, automatic living room blinds, tile flooring throughout, a newer roof, a three-year-old air conditioning system still under warranty, hot water heater and kitchen appliances covered under warranty through February 2027. What truly sets this property apart is the exclusive private beach experience. Imagine leaving your condo and taking a short stroll across Gulf of Mexico Drive to your deeded Gulf-front beach pavilion—a rare luxury on Longboat Key. This private beach oasis offers direct access to miles of pristine sand and the crystal-clear waters of the Gulf of Mexico, without the crowds of public beach access points. Spend your mornings collecting seashells, your afternoons soaking in the Florida sunshine, and your evenings watching unforgettable Gulf Coast sunsets paint the sky in vibrant shades of orange, pink, and gold. The private beach pavilion enhances every visit with convenient showers, restrooms, and dedicated beach chair storage, making spontaneous beach days effortless. Whether you’re taking a peaceful sunrise walk, enjoying a refreshing swim, or simply listening to the waves with your feet in the sand, this exclusive beach access transforms everyday living into a permanent vacation. Beyond the beach, Longboat Harbour delivers an unmatched resort-style lifestyle. Residents enjoy four heated swimming pools with loungers and umbrellas, a fitness center, art studio, game room, clubhouse with banquet facilities, two lighted fishing piers with fish-cleaning stations, kayak and paddleboard launches with storage, a scenic waterfront walking path, deeded covered parking, additional guest parking, and extra storage. For boating enthusiasts, boat slips accommodating vessels up to 34 feet are available via waitlist for an incredibly affordable annual fee, offering direct access to Sarasota Bay and endless days on the water. Whether you’re searching for a full-time residence, seasonal escape, or investment in the Longboat Key lifestyle, this is more than a condominium—it’s an invitation to experience the very best of waterfront and beachfront living in one extraordinary location. Bay views. Private beach. Resort amenities. Endless sunsets. Welcome to paradise.

4340 Falmouth Drive Unit 104, Longboat Key
$200,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Nestled in a beautifully protected marina on the exclusive Longboat Key, this premium 48x20-foot wet slip accommodates vessels up to 43 feet and provides a true vacation lifestyle with full-time live-aboard privileges. Boating enthusiasts will enjoy seamless, unrestricted deep-water access to Sarasota Bay, the Intracoastal Waterway, and the Gulf of Mexico with zero fixed bridges. The slip is fully equipped with robust dual 50-amp and dual 30-amp electrical hookups, while the marina provides comprehensive dockside services including both diesel and gasoline at the fuel dock and complimentary vessel pump-outs by professional dock hands. Owners also enjoy the flexibility to lease the slip to marina-approved vessels, offering excellent investment versatility without requiring a Longboat Key Club membership. Life at the marina combines everyday convenience with resort-style perks, featuring stunning, unobstructed sunrise and sunset views daily. The property includes water, sewer, cable TV, and Wi-Fi, alongside access to a well-maintained bathhouse, coin laundry facilities, a secure package delivery center, and free bicycle rentals. Parking is highly accessible with multiple spaces located directly next to the dock. Ownership integrates you into the Bay Isles HOA, which ensures peace of mind through 24-hour guarded gates, active security, and immaculate common area maintenance. For just $600 a year, owners can also join the walkable Bay Isles Beach Club to enjoy newly renovated beachfront facilities, volleyball nets, and picnic areas with grills. To complete the luxury experience, a complimentary community shuttle is available to transport you directly to the premier shopping and dining at St. Armand's Circle or the Longboat Key Club Resort properties.

2600 Harbourside Drive Unit P-05, Longboat Key
$425,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
Easy access and docking at this 75 ft. x 26 ft. Boat Slip at Longboat Key Moorings Marina on D-dock. Located on the West side of the marina. Ample turning radius between piers, so lots of room to maneuver. Direct access to Sarasota Bay and the ICW; 15 minutes to the Gulf. The deep water marina is as much a luxury resort as any other neighborhood on the island, thanks to individual slip ownership, a Mediterranean-style village and restaurants, shopping (close to Publix, CVS, and other shops), recreational and social activities, on-site maintenance and concierge services. Each slip includes wifi, water, pump out and metered electric, along with trash pick up and dockhands to assist. Longboat Key Moorings is truly a World Class facility. All vessels must be approved prior to closing by the Association. A current photo must be submitted. Max length of vessel allowed is 70 LOA, usable beam is 23 ft at the head of the slip. Each vessel must be approved by the Association's Board of Directors prior to entering the marina by submitting a current photo and boat specs.

2800 Harbourside Drive Unit D-16, Longboat Key
$6,950,000
4 Beds ⋅ 6 Baths ⋅ Emerald Harbor SubDv. ⋅ 34228 Zip Code
Timeless architecture, uncompromising craftsmanship, and spectacular waterfront living converge in this newly completed West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key. This gorgeous home offers expansive indoor-outdoor living with walls of glass that open to covered porches and balconies off of every room, framing tranquil views of the gorgeous pool and spa, the wide canal, Harris Bayou and Sarasota Bay. Features include an elevator that takes you from the garage level to each floor with ease; A chef's kitchen with a separate fully equipped prep kitchen; 4 spacious bedrooms each with their own en-suite. A fire pit, private dock, outdoor shower and pool bath, plus deeded beach access complete the Longboat Key lifestyle. Every luxury amenity expected in a home of this caliber make this a truly exceptional offering.

711 Old Compass Road, Longboat Key
$500,000
Longboat Key Moorings SubDv. ⋅ 34228 Zip Code
An easy access slip with the views to along with the superb amenity package, Slip B-16 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 85 x 29.5, and a usable beam of 25 feet and a long and extra wide finger pier. This 'inside the T-head' slip location provides close proximity to the Marina Village, Restaurant, and Pool. 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 and golf facilities, fitness center, with spa and beach access. The Club also reciprocates with 400 of Clubs throughout the country. 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 80 feet. Beam depends on the vessel type and measure. Vessel must be approved by the Board of Directors prior to entering the Marina. Membership in the Longboat Key Club is required.

2600 Harbourside Drive Unit B-16, Longboat Key
$3,995,000
Bay Isles SubDv. ⋅ 34228 Zip Code
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
$395,000
2 Beds ⋅ 2 Baths ⋅ Twin Shores Mobile Home SubDv. ⋅ 34228 Zip Code
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. ⋅ 34228 Zip Code
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
$569,000
2 Beds ⋅ 2 Baths ⋅ Spanish Main Yacht Club SubDv. ⋅ 34228 Zip Code
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
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