Longboat Key Homes with Boatable Water Water Frontage

Welcome to Longboat Key, a picturesque island town located in the beautiful state of Florida. This charming city is a haven for those seeking a luxurious waterfront lifestyle combined with the tranquility of island living.

Longboat Key is renowned for its pristine beaches, world-class golf courses, and upscale dining and shopping options. Residents and visitors alike can enjoy a wide range of outdoor activities, from boating and fishing to kayaking and paddleboarding.

One of the most coveted features of real estate in Longboat Key is the homes with boatable water frontage. Imagine waking up to stunning water views right from your own backyard, with easy access to the sparkling waters of the Gulf of Mexico. Whether you're looking for a cozy waterfront cottage or a lavish estate, Longboat Key offers a diverse selection of homes to suit every taste and budget.

Living in a home with boatable water frontage in Longboat Key means you can indulge in waterfront living at its finest. Spend your days cruising along the coastline, watching the sunset from your private dock, or simply relaxing in the serenity of your waterfront oasis.

If you're dreaming of a waterfront lifestyle in a vibrant coastal community, Longboat Key is the perfect place to call home. Discover the beauty and charm of this island paradise and find your own piece of waterfront paradise in this idyllic city in Florida.

Newest Longboat Key Homes with Boatable Water Water Frontage

$200,000

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code ⋅ A4701807 MLS ⋅ Active Status

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 ⋅ A4701620 MLS ⋅ Active Status

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

$695,000

Bailey-Dobson SubDv. ⋅ 34228 Zip Code ⋅ A4701851 MLS ⋅ Active Status

Create your custom coastal retreat or bring the seller’s thoughtfully prepared plans to life at 561 Gulf Bay Road. This rare 9,990-square-foot vacant homesite is ideally located in the heart of Longboat Key, between the charm of Anna Maria Island and the sophistication of St. Armands Circle. Bordering the 32-acre Joan M. Durante Community Park, the property offers exceptional privacy, peaceful natural surroundings, and convenient access to scenic walking trails, a picnic pavilion, and picturesque views of Sarasota Bay and the Sarasota skyline. Imagine watching eagles, ospreys, and other native wildlife from your future home or backyard. With no HOA or deed restrictions, you have the flexibility to personalize the available plans or design a custom residence that reflects your vision and lifestyle. The property also includes deeded beach access to a quiet stretch of white sand along the Gulf of Mexico, allowing you to enjoy the best of both Gulf and bay living. Nearby destinations include Euphemia Haye, Harry’s Continental Kitchens, boutique shopping, and a neighborhood deli, with additional dining, recreation, shopping, and entertainment available throughout Longboat Key, Anna Maria Island, and Sarasota. Underground utility improvements throughout the area are complete. Previously prepared plans for a custom single-family residence and an elevation study are available upon request, providing an excellent starting point for your future island home. Buyers should independently verify current building requirements and property suitability. This is a special opportunity to build in one of Longboat Key’s most naturally beautiful and desirable locations. Schedule your private showing and begin planning your Florida coastal lifestyle. Representative Photos Added to listing showcase preliminary renderings showcasing Conditioned Square Footage of 4,936 and Unconditioned Square Footage of 4,053.

561 Gulf Bay Road, Longboat Key

$1,195,000

3 Beds ⋅ 3 Baths ⋅ Fairway Bay SubDv. ⋅ 34228 Zip Code ⋅ A4700558 MLS ⋅ Active Status ⋅ Building 3 - Phase 1 BLDG.

Behind the gates of Bay Isles, this beautifully updated waterfront townhome in Fairway Bay offers the rare convenience of a private deepwater dock accommodating vessels up to 40’. From here, Sarasota Bay, waterfront dining and the Gulf are only minutes away by boat, while peaceful water views become part of the backdrop to everyday living. A stepped walkway welcomes you inside, where more than 2,100+/- sq. ft. unfolds across two thoughtfully designed levels. The moment you enter, soaring 2-story ceilings create an immediate sense of openness, while warm wood flooring, soft neutral tones and carefully selected finishes create an inviting atmosphere throughout. The living room centers around a striking linear fireplace, creating a natural gathering place for relaxing or entertaining. Nearby, the dining area transitions effortlessly into the reimagined kitchen, where white cabinetry with glass panel accents, stone countertops, tile backsplash, breakfast bar and a dedicated coffee station combine beauty with everyday function while keeping the space connected to the surrounding living areas. The primary suite offers a peaceful retreat with its own private terrace overlooking the bay, while the spa-inspired bath features an oversized soaking tub, rainfall steam shower and abundant natural light from an overhead skylight. Two additional bedrooms, along with flexible bonus areas for hobbies, fitness or music, provide comfortable accommodations for family and guests. Multiple terraces throughout the home create inviting places to enjoy the waterfront setting from sunrise through evening. A popular, bayfront and pet-friendly community, Fairway Bay offers a heated pool, spa, fitness center, clubhouse, tennis courts and scenic walking and biking paths. Optional membership to the Longboat Key Club provides access to championship golf, dining, tennis and an exceptional collection of island amenities.

1906 Harbourside Drive Unit 304, Longboat Key

$549,000

2 Beds ⋅ 2 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code ⋅ A4701697 MLS ⋅ Active Status ⋅ Building 5 BLDG.

This well-maintained 2BR/2BA residence in Grand Bay features a large, full-width terrace with views of Sarasota Bay. Floor-to-ceiling glass and multiple terrace access points bring in natural light and make the outdoor space a true extension of the living area. Large-format ceramic tile, high ceilings and a neutral color palette create a bright, comfortable interior. The open living and dining area overlooks the bay, while the oversized terrace provides ample space for outdoor dining, entertaining or relaxing among the tropical landscaping. Double doors lead to the galley-style kitchen, which includes white cabinetry, stone countertops, a tray ceiling, a paneled refrigerator and a window for additional natural light. The primary suite offers generous proportions and corner sliding doors opening directly to the terrace. Its en-suite bath features dual vanities and a spa tub. The spacious guest suite includes a walk-in closet and direct outdoor access. An in-residence laundry room adds convenience - two under-building parking space. Grand Bay residents enjoy a clubhouse, fitness center, two Har-Tru tennis courts, two heated swimming pools and spa. Bay Isles ownership also includes deeded access to the private Bay Isles Beach Club on the Gulf of Mexico, with an on-site attendant, covered gathering areas, grills, changing rooms, restrooms and showers. Separate, optional membership in the Longboat Key Club is also available. Depending on the membership selected, members may enjoy access to 45 holes of golf, tennis and pickleball facilities, a private beach, fitness and wellness programs, a full-service spa, dining, marina amenities and year-round social activities.

3080 Grand Bay Boulevard Unit 512, Longboat Key

$6,950,000

4 Beds ⋅ 6 Baths ⋅ Emerald Harbor SubDv. ⋅ 34228 Zip Code ⋅ A4699408 MLS ⋅ Active Status

Timeless architecture, uncompromising craftsmanship, and spectacular waterfront living converge in this newly completed West Indies-inspired residence in the coveted neughborhood 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

$2,999,999

6 Beds ⋅ 6 Baths ⋅ Sleepy Lagoon SubDv. ⋅ 34228 Zip Code ⋅ TB8533896 MLS ⋅ Active Status

Virtually Staged. Welcome to an extraordinary waterfront estate on coveted Longboat Key, where timeless coastal elegance meets world-class boating. Perfectly situated on a deep-water saltwater canal with a private dock and direct access to the Gulf, this exceptional residence offers the rare opportunity to experience the very best of Florida luxury living just moments from the island's pristine white-sand beaches. Encompassing nearly 4,700 square feet of thoughtfully designed living space, this impressive home features six spacious bedrooms, five-and-a-half bathrooms, a private elevator, and an oversized four-car garage, providing exceptional space for family, guests, luxury vehicles, and all of your boating equipment. Whether you're searching for a full-time residence, seasonal retreat, or premier waterfront investment, this home offers the versatility to comfortably accommodate up to 20 guests. Designed to embrace its breathtaking waterfront setting, expansive balconies span the entire rear of the home, creating multiple outdoor living spaces perfect for morning coffee, sunset cocktails, or entertaining while overlooking the peaceful canal. The luxurious primary suite serves as a private sanctuary with its own waterfront balcony, where tranquil water views become part of your everyday routine. The backyard is a true resort-style oasis featuring a sparkling in-ground pool, generous lounging areas, and a private dock on a deep-water canal with quick, effortless access to the open Gulf. Spend your days boating, fishing, paddleboarding, or cruising to waterfront restaurants before returning home to your own private paradise. At the heart of the home is a stunning chef's kitchen designed for both everyday living and grand entertaining. Featuring a professional gas range, double ovens, dual wine refrigerators, two dishwashers, gorgeous granite countertops, extensive custom cabinetry, a spacious walk-in pantry, and an oversized center island with seating for six, this kitchen is equally impressive in both form and function. The open-concept floor plan flows seamlessly into elegant living and dining spaces filled with natural light, creating an inviting atmosphere ideal for entertaining on any scale. A secondary kitchenette and expansive game room offer incredible flexibility for hosting guests, creating a private guest suite, or accommodating multi-generational living with ease. For added peace of mind, all major mechanical systems and significant capital improvements have been completed within the past four years, allowing the next owner to simply move in and enjoy the home from day one. Ideally located just minutes from Longboat Key's award-winning beaches, championship golf, fine dining, marinas, boutique shopping, St. Armands Circle, and the cultural attractions of downtown Sarasota, this exceptional property represents a rare combination of luxury, location, deep-water boating, and island lifestyle. Opportunities to own a waterfront home of this caliber—with six bedrooms, deep-water dockage, Gulf access, a four-car garage, and the ability to comfortably host family and friends on one of Florida's most prestigious barrier islands—are truly few and far between. Ride your bike to Anna Maria Island for night life, restaurants and shopping. Beautiful Gulf beaches are just steps away from your new house! Please feel free to check out virtual tour https://next.frame.io/share/09e65a61-fa88-4c36-8474-69609bc826e6/view/f03db32d-b617-4f1c-85ec-54ccc2a57dae

614 Norton Street, Longboat Key

$500,000

Longboat Key Moorings SubDv. ⋅ 34228 Zip Code ⋅ A4700188 MLS ⋅ Active Status

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

$1,050,000

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code ⋅ A4699368 MLS ⋅ Active Status ⋅ Building 2 BLDG.

Virtually Staged. Wide views of Sarasota Bay, the Harbourside golf course and downtown Sarasota define this well-maintained 3-bedroom, 3.5-bath residence at Grand Bay. Floor-to-ceiling glass keeps the scenery in focus and brings natural light into the main living areas. The living room opens to a large terrace overlooking the golf course, bay and skyline, while tray ceilings and tile flooring contribute to the open feel. The kitchen features wood cabinetry, a center prep island, paneled refrigerator and adjoining dining area. Nearby, a sitting area includes textured accent walls and built-in shelving. The primary suite also opens to the terrace and offers bay views and an oversized walk-in closet. The adjoining bath includes a soaking tub, glass-enclosed shower and private water closet. Two additional guest suites each have an en suite bath, and an in-residence laundry room adds convenience. Grand Bay amenities include a clubhouse, two resort-style pools and spas, a fitness center with saunas and Har-Tru tennis courts, all within the gated Bay Isles community. Ownership also includes membership in the private Bay Isles Beach Club, with gated Gulf access, covered gathering and picnic areas, barbecue grills, restrooms and changing facilities. Optional membership in the Longboat Key Club is available separately. Depending on membership category, amenities may include 45 holes of golf, the Tennis Gardens with 20 Har-Tru courts, private dining venues and lounges, beach and pool facilities, a spa, fitness and wellness facilities, member events and Longboat Key Club Moorings.

3040 Grand Bay Boulevard Unit 232, Longboat Key

$1,349,000

3 Beds ⋅ 4 Baths ⋅ Grand Bay SubDv. ⋅ 34228 Zip Code ⋅ A4699372 MLS ⋅ Active Status ⋅ Bldg. 2 BLDG.

Virtually Staged. Set within Grand Bay on Longboat Key, this renovated 3BR/3.5BA residence offers panoramic views of Sarasota Bay, the Harbourside golf course and the city skyline. With 2,250 square feet, walls of glass bring the scenery into nearly every main living space, creating an inviting blend of comfort, openness and relaxed Bay Isles elegance. Floor-to-ceiling windows with plantation shutters frame the views, while tile flooring, neutral tones and recessed lighting create a warm, understated setting. The living room opens to a view overlooking the golf course, a tranquil pond and Sarasota Bay - ideal for quiet mornings or entertaining. The kitchen flows easily into the living areas and features white cabinetry, stone countertops and backsplash, and stainless-steel appliances. The primary suite offers warm wood flooring and a spacious bath with dual vanities, a makeup area and a large walk-in shower. Two guest suites each include a private en suite bath. An in-residence laundry room and one covered parking space complete the home. Grand Bay residents enjoy a clubhouse, designer-appointed lobby, two pools and spas, a fitness center with saunas, and Har-Tru tennis courts. Bay Isles privileges include gated entry, scenic walking paths and access to the private Gulf-front Bay Isles Beach Club, featuring white sand, an attended entrance, covered picnic and entertaining areas, tiki huts, barbecue grills, restrooms, changing rooms and beach-equipment storage. Optional membership is also available at the Longboat Key Club. Amenities vary by membership category and include 45 holes of championship golf, 20 Har-Tru tennis courts, private beach and pool facilities, spa and fitness facilities, restaurants and lounges, club events and marina access.

3040 Grand Bay Boulevard Unit 225, Longboat Key

$425,000

2 Beds ⋅ 2 Baths ⋅ Longboat Harbour North SubDv. ⋅ 34228 Zip Code ⋅ A4700306 MLS ⋅ Active Status ⋅ 4390 BLDG.

Seeking an opportunity to enjoy the Longboat Key lifestyle? This turnkey, two-bedroom, two-bath residence overlooks the Intracoastal Waterway and offers 1,072 square feet of living space. The view out the back of the condominium is simply magical. Sparkling water, beautiful sunsets, and, of course, manatees. This residence comfortably sleeps six, has direct access to the Harbour walking path, and also includes an in-home washer and dryer. Longboat Harbour offers an extensive collection of resident amenities, including a dedicated parking space, sauna, outdoor pools, putting green, kayak and paddleboard launch with storage, pickleball and tennis courts. Boat docks are available on a first-come, first-served basis for less than $600 annually, subject to availability. Residents also enjoy a recreation center with activities including poker, table tennis, billiards, arts and crafts, woodcarving and grilling areas. A deeded, private beach provides convenient access to the Gulf, along with storage, restrooms and showers. The condominium association has completed new roofing, providing added peace of mind. If you've been waiting for the right way to live, I think you just found it.

4390 Exeter Drive Unit 107, Longboat Key

$3,995,000

Bay Isles SubDv. ⋅ 34228 Zip Code ⋅ A4698387 MLS ⋅ Active Status

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

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