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Long Boat Key

One of the most popular communities provided by Michael Graf

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.

One of the most popular communities provided by Michael Graf

507

# of Listings

2

Avg # of Bedrooms

$867

Avg. $ / Sq.Ft.

$1,539,132

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

507 Properties Found. Page 3 of 34.

Longboat Key Waterfront Estate with Rare Beach and Boating Access. Designed by Stofft Cooney Architects and built in 2022 by Perrone Construction, one of the Gulf Coast’s premier luxury builders, this stunning coastal residence is a rare offering that blends modern design, structural integrity, and an exceptional location. Positioned on the desirable northern end of Longboat Key, the home offers a lifestyle few can match, with both deeded beach access directly across the street and canal frontage in the backyard. Where most homes require a choice between Gulf or Bay, this property offers the best of both. Step inside to discover a layout designed for both comfort and sophistication. The main level features a serene primary suite with a spa-inspired bathroom, a seated vanity, and a custom walk-in closet. A thoughtfully planned home office includes a custom built-in desk with dual workstations, offering dedicated space for both homeowners. The open-concept living area flows effortlessly into the designer kitchen, outfitted with quartz counters, Thermador appliances, a paneled refrigerator and freezer, wine fridge, and ice maker. A hidden walk-in pantry provides additional prep space and ample storage. Upstairs, a central family lounge connects three en-suite bedrooms, two with tranquil canal views where manatees are often spotted lingering at the water’s surface. The upper level is easily accessed by both a residential elevator and a beautifully crafted staircase with integrated storage. Every room has been carefully curated to reflect the home’s effortless luxury. For buyers seeking a fully realized, move-in-ready experience, furnishings can be negotiated separately. Outdoor living is elevated with a heated saltwater pool and spa, expansive lounging and dining terraces, and a fully equipped summer kitchen featuring stone counters, a Lynx grill, and built-in refrigeration, all protected by push-button retractable hurricane shutters. A dedicated pool bath adds convenience and keeps wet feet out of the house. The private dock includes a 16,000-pound boat lift, a 4,500-pound kayak or jet ski lift, plus additional space to dock a larger vessel in the water. The dock is fully outfitted with shore power, running water, integrated lighting, and a fish-cleaning station, ready for both adventure and convenience. Built high and dry, the home remained fully protected during recent storms, a true reflection of the enduring quality behind its construction. Combining beauty, function, and peace of mind, this is a rare opportunity to enjoy the very best of Longboat Key living, free from compromise.

LONGBOAT KEY

5840 GULF OF MEXICO DRIVE

4 Beds

4 Baths

5,500 Sq.Ft.

$5,280,000

MLS#: A4670094

Welcome to 585 Gunwale Lane, a rare, full-bayfront offering in the desirable community of Country Club Shores on southern end of Longboat Key. On a .36-acre bayfront parcel with 117 feet on Sarasota Bay and 123 feet on a deepwater canal, this residence is a boater’s paradise. A newer seawall and 58-foot dock (2022) with a 24,000-pound boat lift assure easy access to Sarasota Bay and the Gulf of Mexico. On the bay side, Ghost Island sandbar emerges at low tide, creating a natural haven that attracts abundant wildlife and offers fantastic shelling. It also serves as a natural barrier, providing protection during storms. On the Gulf side, deeded access to an exclusive community beach is just a half-mile away. Whether you’re heading out for a day on the water or popping over to St. Armands Circle for dinner and shopping, this home puts you in the center of it all. The residence spans 4,733 square feet and includes three bedrooms and three-and-a-half baths. A soaring 20-foot ceiling defines the living room, where wall-to-wall built-ins create a refined focal point. The dining room opens to a remodeled kitchen outfitted with Graber wood cabinetry and professional-grade Frigidaire appliances. The primary bedroom is on the second floor, featuring a private bayfront balcony, dual walk-in closets, and an adjoining 270-square-foot bonus room ideal for a home office or wellness retreat. Outdoor amenities include a bayfront pool and spa for enjoying Florida sunsets. Additional highlights include impact-resistant windows and doors, and a two-car garage. For those who want to design and build their dream home, this property offers a spectacular location. Imagine a custom rooftop deck with breathtaking 360-degree views of the bay, Gulf, and downtown Sarasota. This is an opportunity to create something extraordinary. This exceptional property presents a rare opportunity to park your boat in the backyard and join the privileged few who call this well-established neighborhood home. By land or by sea, welcome to your fabulous Florida lifestyle!

LONGBOAT KEY

585 GUNWALE LANE

3 Beds

3 Baths

6,609 Sq.Ft.

$5,225,000

MLS#: A4657691

Bay Isles Harbor, Longboat Key - Stunning 4BR/5.5BA, 5,080 SF waterfront home in the prestigious Bay Isles Harbor section of Longboat Key. This architectural masterpiece features a dramatic great room with soaring tongue-and-groove ceilings and floor-to-ceiling windows showcasing sweeping water views. The circular kitchen offers stone counters, top-tier appliances, and integrated Lutron lighting, audio, and video systems. The first-floor primary suite opens to the pool and screened patio with a spa-style bath and private office. A newer 32x23 guest suite includes two Murphy beds, entertainment area, steam shower, and sauna. Enjoy a private dock on protected deep sailboat water with a 12,000 lb. lift. Bay Isles residents enjoy gated security and access to the exclusive Bay Isles Beach Club on the Gulf of Mexico.

LONGBOAT KEY

510 HARBOR GATE WAY

4 Beds

5 Baths

6,534 Sq.Ft.

$5,100,000

MLS#: A4671696

#A4661312

LONGBOAT KEY

569 BAYVIEW DRIVE

4 Beds

4 Baths

5,282 Sq.Ft.

$5,049,000

MLS#: A4661312

#A4665054

LONGBOAT KEY

6601 GULFSIDE ROAD

5 Beds

3 Baths

3,492 Sq.Ft.

$5,000,000

MLS#: A4665054

New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind.
Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms.
Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.

LONGBOAT KEY

530 DE NARVAEZ DRIVE

4 Beds

4 Baths

5,282 Sq.Ft.

$4,995,000

MLS#: A4669195

Experience beachfront luxury in this spacious 3,800-square-foot 3-bedroom, 3.5-bath + den/office residence in the prestigious En Provence community on Longboat Key. A private elevator opens to a grand foyer with marble floors and tray ceilings. Expansive glass sliders in the living room frame stunning Gulf views and lead to an oversized terrace, perfect for seamless indoor-outdoor living. The expansive terrace is ideal for entertaining, featuring a built-in gas grill and outdoor cooking space overlooking the beach and lush grounds. The kitchen is both stylish and functional, featuring a center island, white cabinetry, and pristine white stone countertops. High-end appliances, including a natural gas cooktop, enhance the space, while a bold blue tile backsplash adds a striking contrast. The adjacent eat-in area, with Gulf views and a built-in desk, enhances both charm and practicality. The primary suite offers terrace access and a spa-like bath with a soaking tub, dual vanities, a makeup area, and a glass-enclosed shower. Two guest suites each include en-suite baths and scenic views. A large office provides flexibility and could easily convert into a fourth bedroom. Additional features include an in-residence laundry room and 2 car garage. Set on nearly six acres of pristine beachfront, En Provence blends elegance and convenience with a clubhouse, resort-style pool and spa, fitness center, and 24-hour guard gate. For those seeking additional amenities, optional membership to the nearby Longboat Key Club provides access to world-class golf, tennis, dining, a marina, and a spa.

LONGBOAT KEY

2161 GULF OF MEXICO DRIVE 3

3 Beds

3 Baths

4,600 Sq.Ft.

$4,995,000

MLS#: A4643048

Price reduced

#A4657152

LONGBOAT KEY

670 OLD COMPASS ROAD

5 Beds

5 Baths

5,792 Sq.Ft.

$4,925,000

MLS#: A4657152

Experience unparalleled luxury in this beautifully updated 3-bedroom condo at the highly coveted L’Ambiance condominium behind the exclusive gates of the Longboat Key Club. This seventh floor sabal floorplan offers sweeping views of the Gulf of Mexico, the Bay and downtown Sarasota. The exceptional renovation was a collaboration between interior designer Chris Sloan and Markley Construction, known for their expertise in high end renovations at L’Ambiance. Fresh paint and designer wall treatments, white oak floors, and stunning new lighting enhance this flowing floor plan, where natural light cascades over spacious rooms designed for gorgeous entertaining and everyday moments. The kitchen has been reimagined to enhance functionality and opened to capture gorgeous views, creating a bright and airy floorplan with ample countertop space. A defining focal point, the dreamy white kitchen features Wolf and Sub-Zero appliances, quartzite countertops, white oak accents and plentiful storage. A stunning wet bar with a Sub-Zero wine fridge and refrigerator drawers provides a seamless connection from the kitchen to the great room. Included in this renovation was the transformation of the den/office into a third usable bedroom, with pocket doors for privacy. This is a rarely seen feature in L'Ambiance and is perfect for out of town guests. The bathrooms have been completely renovated with the latest design trends, and the primary bath offers a luxurious spa-like retreat with a separate makeup vanity. No detail has been overlooked: solid core doors, new baseboards, fresh paint, custom white oak beams, electric window treatments, upgraded hardware and impact rated windows and sliding glass doors through Mullets have been installed. Step outside and prepare to be captivated by the breathtaking views that surround you. Enjoy both sunrise and sunset from your expansive balconies—one offering panoramic views of the downtown skyline and sparkling Bay, and the other providing a front-row seat to the mesmerizing Gulf sunsets. Whether you’re relaxing on your terrace or watching the lights of downtown illuminate the evening sky, this residence delivers a front-row view of the best of Longboat Key. L’Ambiance residents enjoy luxury amenities such as 24-hour security, a 240' lap pool and patio, hot tub that is just steps to the sparkling Gulf waters. There are also 2 well maintained Har-Tru tennis courts. Building amenities include a full time manager and staff with concierge services, fitness center, clubhouse with catering kitchen, individual wine lockers, library, game room and 3 guest suites, storage, and a secured garage parking, surrounded by lush landscaping and walkways. Two parking spots are included with this condo with one of the spots being conveniently located right by the elevator. Furnishings may be available with separate agreement.

LONGBOAT KEY

435 L AMBIANCE DRIVE J703

3 Beds

2 Baths

3,650 Sq.Ft.

$4,795,000

MLS#: A4667475

New on site 1 day ago

#A4673592

LONGBOAT KEY

610 YARDARM LANE

4 Beds

4 Baths

4,138 Sq.Ft.

$4,700,000

MLS#: A4673592

Build your dream beachfront estate on nearly three-quarters of an acre on exclusive North Longboat Key. With 100 feet of private Gulf frontage, this rare homesite offers endless views of turquoise waters spectacular sunsets and direct access to powder sand just steps from your future doorstep.
Set within a rising luxury enclave, this prime property is moments from the new St. Regis Resort and the Longboat Key Club, offering world-class golf, tennis, dining, and five-star amenities. Enjoy the charm of nearby Anna Maria Island and the upscale shopping and cultural experiences of St. Armands Circle.
This is one of the last opportunities to create a custom beachfront retreat in one of the Gulf Coast’s most coveted locations.

LONGBOAT KEY

6453 GULFSIDE ROAD

None Beds

None Baths

0.7 acres

$4,550,000

MLS#: A4661066

Gulf-Front Luxury Living at Vizcaya on Longboat Key!
Experience refined coastal living in this exceptional three-bedroom residence at Vizcaya at Longboat Key, a boutique beachfront community offering the comfort of a single-family home paired with first-rate amenities. Positioned directly on the Gulf, this residence captures mesmerizing beach views and spectacular sunsets from nearly every vantage point.
A private courtyard entrance welcomes you into an elegant foyer that sets the tone for the home’s sophisticated design. Inside, an open-concept floor plan features beautiful hardwood flooring, custom ceiling treatments, designer lighting, and architectural built-ins that create a seamless flow between living, dining, and entertaining areas. Expansive walls of impact glass fill the space with natural light while framing the endless Gulf panorama.
The chef’s kitchen is a masterclass in both form and function, appointed with Wolf appliances, solid-wood cabinetry, stone countertops, and a generous island for casual dining or hosting. The primary suite serves as a serene private retreat with terrace access, dual walk-in closets, and separate his-and-hers bathrooms, each finished with spa-inspired detailing. A guest wing with sitting room, terrace, and private entrance ensures comfort and privacy for visitors. Plantation shutters, ceiling fans, and impact windows/doors/sliders complement the home’s thoughtful upgrades.
Outdoor living reaches new heights on the 1,000-square-foot wraparound terrace, which includes a built-in outdoor kitchen and gas grill—ideal for al fresco dining while enjoying vivid sunsets. A private two-car garage with additional storage offers both convenience and security.
Residents of Vizcaya enjoy a resort-style lifestyle curated by full-time, on-site staff. The clubhouse hosts resident gatherings and features dining and lounge areas, a catering kitchen, and game rooms. The fitness center includes saunas, steam rooms, massage suites, and a water treadmill, while outdoor amenities include a heated Gulf-front pool and spa, private fishing pier, and lush landscaped grounds. Recent community updates include new roofs (2024), upgraded elevator systems, fire alarms, and refreshed landscaping.
Vizcaya’s gated setting offers 24-hour security, concierge-level management, and full-service maintenance and housekeeping—ensuring effortless ownership and complete peace of mind.
Perfectly positioned on Longboat Key’s pristine Gulf shoreline, this residence is minutes from St. Armands Circle, downtown Sarasota, and the island’s acclaimed dining and tennis clubs. Explore nearby Mote Marine Laboratory, The Longboat Key Club, Bayfront Park, or the Ringling Museum of Art, all within easy reach. With its rare blend of privacy, elegance, and proximity to Sarasota’s finest attractions, this Vizcaya home embodies the ultimate Gulf-front lifestyle.

LONGBOAT KEY

2333 GULF OF MEXICO DRIVE 1A2

3 Beds

2 Baths

4,036 Sq.Ft.

$4,500,000

MLS#: A4672009

Discover an elegant and gracious two-bedroom residence featuring spacious rooms, expansive glass windows, and soaring ceilings that create an airy, inviting atmosphere. The well-appointed gourmet kitchen boasts top-of-the-line Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, and a side-by-side refrigerator, perfect for culinary enthusiasts. Retreat to the large owner's suite, complete with a luxurious primary bath that features double vanities, a deep soaking tub, a frameless walk-in shower, and a private water closet. The residence is being sold furnished from Restoration Hardware. Host unforgettable gatherings on your terrace, equipped with an outdoor gas grill and views of Sarasota Bayfront. Residents will have the ease and convenience of a private 2-car garage on the first level with easy access to your semi-private elevator opening directly into your residence. Nestled within the first branded residential community and ultra-luxe 5-star resort on the Gulf of Mexico, The Residences at The St. Regis Longboat Key blend legendary service with the serene allure of a seaside getaway on the secluded barrier island of Longboat Key, FL. Spanning over 17 acres with 800 feet of direct beachfront, this community offers unparalleled amenities, including the signature St. Regis Butler and Concierge services, a world-renowned St. Regis Spa, in-residence dining, a private resident-only pool and spa, a Clubhouse, a fitness center, and beachside cabanas. Experience luxury living at its finest. Welcome home to The St. Regis Longboat Key.

LONGBOAT KEY

1591 GULF OF MEXICO DRIVE 413

2 Beds

2 Baths

2,800 Sq.Ft.

$4,499,000

MLS#: A4627935

Price reduced

BEACH FRONT OPPORTUNITY on Longboat Key! Rare chance to own DIRECT GULF FRONT property on the coveted south end of Longboat Key in Sarasota county. This charming, 1955 beach cottage sustained significant hurricane damage and is now being sold AS-IS for land value only. No HOA fees! Build your dream coastal retreat on this prime GULF-front lot and enjoy breathtaking sunsets, white-sand beaches- just steps to Publix grocery, 1.5 miles to the stunning St. Regis resort, and easy access to nearby St Armand’s dining/shopping, downtown Sarasota, golf, and marinas. You do not want to miss this opportunity to create your own piece of paradise on BEAUTIFUL Longboat Key!

LONGBOAT KEY

2819 GULF OF MEXICO DRIVE

3 Beds

2 Baths

2,267 Sq.Ft.

$4,499,000

MLS#: A4669533

Price reduced

The Quintessence of Coastal Living: A British West Indies Masterpiece on Longboat Key - Where Architecture Meets Paradise. Offered turn-key, this exquisite 4,000+ sq. ft., 4-bedroom, 4.5-bath residence in Longboat Key’s prestigious Bonaire subdivision is a rare union of refined British West Indies architecture and the serene beauty of Florida’s Gulf Coast. Every inch of this home has been thoughtfully crafted to evoke a sense of effortless luxury—where sun-kissed days and gentle Gulf breezes blur the line between indoors and out. From the moment you step through the grand entrance, you’re embraced by light, texture, and tranquility. Creamy finishes, warm woods, and bespoke millwork elevate every space, while expansive windows and French doors invite in the turquoise glow of the Gulf and the soothing rhythm of coastal life. Main Level Elegance - The heart of the home features an open-concept chef’s kitchen with top-of-the-line appliances: a Wolf 6-burner gas range with custom vent hood, dual Asko dishwashers, Sub-Zero refrigerator/freezer, Wolf convection/microwave, and a 50-bottle wine captain. Quartz countertops, artisan pendant lighting, and a massive island with farmhouse sink make this space as beautiful as it is functional. The adjoining dining and great room flow effortlessly to an expansive balcony - perfect for indoor-outdoor entertaining. The main-floor Primary Suite offers tray ceilings, shiplap accents, dual walk-in closets, and a spa-inspired bath with soaking tub, double-entry stone shower, and sparkling stone vanities. Two additional ensuite guest rooms on this level echo the home’s airy, coastal elegance, and exceptional quality. Upper-Level Retreat - Ascend to a private owner’s sanctuary with dual custom closets and a lavish bath adorned with blue calcite counters, glass mosaic tile, and a freestanding tub. This level includes a substantial private balcony with access to the upper-level viewing balcony. The Observation Deck - Crowning the home is the ultimate vantage point—a “crow’s nest” with panoramic Gulf and Sarasota Bay views. It’s here you’ll end each day watching sunsets paint the horizon in unforgettable color. Resort-Style Outdoor Living - The pool retreat is an absolute showstopper - pocketing sliding doors reveal coral stone terraces, a resort-style pool with sun shelf and tiled cocktail table, a 10-person spa, and a fully equipped outdoor kitchen with seating for eight. The entire area is lined with an automatic insect elimination system to ensure you can enjoy the outdoors all year long. Optical lighting enhances the overflowing water features which seem to dance in the glow of firelight, creating the perfect setting for stargazing or nightcaps. The community provides private beach access and is close to world-class golf, tennis, fine dining, and the largest deep-water marina on the Gulf coast. This is more than a home - it’s a sanctuary, a work of art, and a lifestyle. Delivered exactly as you see it, fully furnished and ready to enjoy, this British West Indies masterpiece awaits the one discerning buyer ready to claim the very best of Longboat Key coastal living.

LONGBOAT KEY

5005 GULF OF MEXICO DRIVE 5

4 Beds

4 Baths

6,437 Sq.Ft.

$4,424,000

MLS#: A4661988

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