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Long Boat Key

One of the most popular communities provided by The Graf Group of Coldwell Banker

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 The Graf Group of Coldwell Banker

311

# of Listings

2

Avg # of Bedrooms

$1,261

Avg. $ / Sq.Ft.

$2,097,322

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

311 Properties Found. Page 2 of 21.

An exceedingly rare offering within the exclusive Bay Harbour enclave of Bay Isles on Longboat Key, this extraordinary peninsula estate delivers exceptional privacy, dramatic Sarasota Bay views, and direct boating access to both the Intracoastal Waterway and the Gulf of Mexico. Positioned at the end of a quiet cul-de-sac on a three-sided waterfront peninsula, the property features two private docks with water and electric, including one with a 15,000-lb lift designed for easy access. The Gulf is reachable through the nearby jetty with drawbridge, with an additional route via the John Ringling Bridge. The seawall was newly capped in 2020, and the pier deck and boat lift controls were replaced in 2025, ensuring superior waterfront infrastructure.
Extensively rebuilt and structurally engineered, the residence is warm, refined, and filled with natural light, capturing sweeping bay views from nearly every room. The chef-inspired kitchen showcases custom rare wood cabinetry, an extended breakfast bar, a three-sink layout, double dishwashers, Sub-Zero refrigerator, Wolf warming drawer, standalone ice maker, and beautifully finished wood ceilings.
The living and dining areas feature a custom jazz club floor and open seamlessly to a wraparound screened lanai, fully reconstructed with multilayer waterproof construction, a rich teak ceiling, and an open-sky section ideal for coastal breezes and stargazing. Multiple seating and dining areas create effortless indoor-outdoor living with uninterrupted water views.
Outdoors, the pool area offers a private retreat surrounded by tropical landscaping and expansive travertine decking designed for both relaxation and entertaining. A custom palm-terrace garden enhances the tranquil ambiance along the east side of the deck.
All bathrooms have been fully remodeled with premium finishes, floor-to-ceiling tilework, and frosted glass shower doors. The primary suite features an elegant, spa-like bath designed with refined materials.
Additional upgrades include hurricane-rated windows and doors, 5-ton A/C units installed in 2024 and 2025, all-new plumbing, electrical, and HVAC ductwork, a whole-house water purification system, a full security camera system, and extensive structural improvements completed under engineering oversight. Exterior enhancements include landscape lighting, a resurfaced epoxy garage floor with mini-split A/C, and cell-foam insulation for efficiency.
Residents of Bay Isles enjoy private Gulf beach access at the Bay Isles Beach Club, offering tiki huts, restrooms, BBQ areas, and gathering spaces. The gated community provides 24/7 security, community pools, and miles of shaded sidewalks ideal for walking and cycling.
With its unrivaled peninsula setting, exceptional boating amenities, unmatched privacy, and sweeping water views at every turn, this estate represents one of Longboat Key’s most remarkable waterfront opportunities—an extraordinary residence defined by craftsmanship, luxury, and coastal elegance.

LONGBOAT KEY

560 HARBOR COVE CIRCLE

3 Beds

3 Baths

3,485 Sq.Ft.

$7,900,000

MLS#: A4672059

Designed by award-winning architect, John Cooney, and built by Sarasota’s premier coastal homebuilder, Perrone Construction, this mid-Key classic is simply among Longboat Key’s finest homes.
Walk in to this fully furnished home which is steps from the beach and with expansive Gulf and Bay views, this masterpiece offers more than 4300 square feet of refined interiors on the main living floors together with multiple large lanais and balconies. A beautiful foyer, large family room, and home gym are featured on the ground floor, along with an oversized three-car garage and storage room.
The quality of the home’s design and construction are matched by the charm of the interior finishes and amenities. The living areas incorporate beautiful ceiling elevations, along with custom wide-plank hardwood, Italian porcelain tile, and custom plantation shutters and drapes. The Great Room flows into the chef’s kitchen which features custom cabinetry, quartz countertops, Wolf and SubZero appliances, and a temperature-controlled 275 bottle wine room. Designed for easy entertaining, the Great Room opens onto a large lanai with its gas fireplace and grill, and gorgeous Gulf and sunset views. Adjoining the kitchen is a perfect dining room with its own balcony and Gulf views, as well as a large family office/bonus room with custom cabinetry and bookshelves. The Lutron system controls both the lighting and the custom drapes and shades. The home’s elegant chandeliers and sconces bathe its interior with gracious warmth.
The beautiful master suite on the main floor includes a bedroom cathedral ceiling and access to the outdoor lanai. The master bath features custom cabinetry, porcelain tile, a large steam shower, and is plumbed for a master bathtub.
Three spacious guest suites, a gathering lounge, and balconies with Gulf views are found on the second living floor. A private elevator connects all levels.
Both the home and exterior grounds are designed for year-round, low-maintenance living. An extensive landscape refresh in 2023 included new turf and lighting, an outdoor shower, and a great fire pit area for entertaining. Lush landscaping and a tranquil pool setting provide both screening and privacy. The home features remote controlled screening and storm shutters, extensive use of Azek composite, and other low-maintenance materials, along with a gas generator, whole-house water filtration system, central vacuum, and much more.
With miles of pristine beach and bay to explore and with the abundant cultural, dining, and shopping amenities of Sarasota, St. Armand’s Circle, and Anna Maria Island nearby, this timeless home delivers the very best of Longboat Key living.

LONGBOAT KEY

5005 GULF OF MEXICO DRIVE 4

4 Beds

4 Baths

4,630 Sq.Ft.

$7,495,000

MLS#: A4673495

#A4697907

LONGBOAT KEY

7094 LONGBOAT DRIVE E

6 Beds

6 Baths

4,776 Sq.Ft.

$6,995,000

MLS#: A4697907

Price reduced

This spectacular waterfront pool home was just completed in 2026 and built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key that offers expansive water views of the wide canal, and Harris Bayou from every room. Walls of glass open to covered porches with remote screens that allow for easy indoor-outdoor living. Two primary suites, each with large, gorgeous en suites, will make it hard to choose. Features include an incredible chef's kitchen with a separate fully equipped prep kitchen; All of the spacious bedrooms have their own en-suite and access to a covered balcony and all have the stunning views; 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.

LONGBOAT KEY

711 OLD COMPASS ROAD

4 Beds

4 Baths

4,274 Sq.Ft.

$6,495,000

MLS#: A4699408

Rarely does an estate-sized Gulf-front lot of this stature become available on the northern end of Longboat Key. 6351 Gulf of Mexico Drive presents a truly exceptional 100-foot by 388-foot direct beachfront parcel — nearly 39,000 square feet of pristine Gulf of Mexico frontage. This distinguished property stands as one of the final remaining full beachfront estate-sized lots on Longboat Key, offering a rare and significant opportunity. Commanding sweeping, unobstructed views of the turquoise Gulf waters and the iconic white-sand shoreline, the site serves as a unique blank canvas for the creation of a bespoke oceanfront residence. The expansive and generously proportioned dimensions provide unparalleled design flexibility, allowing the accomplished buyer to fully realize a custom legacy property tailored to the highest standards of coastal elegance, privacy, and sophistication. Ideally situated, the property enjoys convenient proximity to the prestigious Longboat Key Club with its 45 holes of championship golf, tennis facilities, and fine dining. World-class restaurants are moments away, including The Shore, Whitney’s, Mar Vista, Euphemia Haye, and Lazy Lobster. Additionally, St. Armands Circle offers exceptional shopping and dining, while the fine and performing arts venues of downtown Sarasota are easily accessible. Positioned among notable residences yet defined by its substantial scale and immediate beach access, this parcel delivers the rare combination of exclusivity and architectural freedom. It is an offering for the discerning individual who has earned the right to create precisely what they envision — a timeless private sanctuary in one of Florida’s most prestigious coastal communities. Private showings by appointment.

LONGBOAT KEY

6351 GULF OF MEXICO DRIVE

None Beds

None Baths

0.88 acres

$6,495,000

MLS#: A4691982

Welcome to an exceptional Gulf-front residence within the prestigious Aria community on the coveted south end of Longboat Key where refined coastal living meets timeless elegance. Set along 300 feet of pristine private shoreline, this extraordinary property offers a rare opportunity to experience true beachfront luxury in one of Sarasota’s most exclusive enclaves.
Beyond the gated entrance, Aria unveils a serene, resort-inspired setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion that serves as the community’s elegant social centerpiece.
This impeccably designed, residence spans nearly 4,000 square feet and is accessed via a private elevator, opening to a grand foyer and expansive, light-filled interiors. Recent enhancements include freshly painted cabinetry throughout the home. The thoughtfully curated open-concept floor plan seamlessly integrates sophisticated living and dining spaces with a chef’s kitchen, creating an ideal environment for both everyday living and elevated entertaining.
Walls of floor-to-ceiling glass and soaring ceilings invite natural light while framing sweeping, unobstructed views of the Gulf. Expansive wraparound terraces provide the perfect setting to enjoy breathtaking sunsets and coastal breezes from nearly every room.
The gourmet kitchen is a statement of both form and function, featuring premium quartz surfaces, freshly painted custom wood cabinetry, and top-tier appliances by Wolf and Miele. The primary suite serves as a private sanctuary, offering a spa-inspired retreat with dual baths connected by an oversized walk-in shower an exceptional design element rarely found.
Two additional ensuite bedrooms provide luxurious accommodations for guests, while a dedicated office or optional fourth bedroom adds versatility. A bonus room offers additional flexibility for hobbies, media, or storage.
Residents of Aria enjoy an unparalleled suite of amenities, including a beachfront pool and spa, state-of-the-art fitness and yoga studios, massage room, and a private wine cellar. A full-time onsite caretaker ensures a seamless, service-oriented lifestyle. The residence also includes a private, oversized two-car dehumidified garage. Don't miss the NEW video tour.

LONGBOAT KEY

2251 GULF OF MEXICO DRIVE 301

4 Beds

4 Baths

3,921 Sq.Ft.

$5,999,000

MLS#: A4658325

Private island living on Jewfish Key, one of eight homes, accessible by boat only. This rare offering presents a lifestyle few will ever experience: a secluded island sanctuary surrounded by the turquoise waters of Longboat Pass and the Gulf Coast’s natural beauty. An address like this comes up for sale about once a generation. 7143 La Lenaire is on the market for the first time in more than two decades.

The home is a custom built, over 2,700 square feet of living space designed to embrace panoramic water views and effortless indoor-outdoor living, four bedrooms and four baths, finished in 2011 on a 1.24-acre titled lot with roughly 300 feet of water frontage. From the island you are minutes by water to Longboat Key, St Armands Circle, and Anna Maria Island.

Every room captures breathtaking western-facing vistas, creating a constant backdrop of sparkling water, coastal breezes, and unforgettable sunsets.
The main living areas open onto covered outdoor space and frame the sunset over the intercoastal waters, and the evening light fills the rooms. It was built to handle a quiet weekend or a full house of guests.

The private deep-water dock provides immediate boating access to Sarasota Bay, the Intracoastal Waterway, Longboat Key Pass, and the Gulf of Mexico, making this a true boater’s paradise.

Jewfish Key is a hidden gem spanning approximately 38 acres, offering a level of privacy and tranquility rarely found along Florida’s Gulf Coast. Surrounded by pristine shoreline, sandbars, native wildlife, and crystal-clear waters, the island delivers an unmatched blend of exclusivity and natural beauty while still being conveniently located near Longboat Key, Anna Maria Island, and Sarasota’s world-class dining, shopping, and entertainment.

Whether used as a private family compound, luxury waterfront getaway, or one-of-a-kind investment opportunity, 7143 La Lenaire Drive represents a truly irreplaceable island lifestyle.

Turn Key - Furnished.

LONGBOAT KEY

7143 LA LENAIRE DRIVE

4 Beds

4 Baths

2,721 Sq.Ft.

$5,995,000

MLS#: A4694196

#A4691731

LONGBOAT KEY

530 JESSMYTH DRIVE

None Beds

None Baths

0.28 acres

$5,985,000

MLS#: A4691731

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

6441 GULFSIDE ROAD

None Beds

None Baths

0.71 acres

$5,600,000

MLS#: A4692771

Discover an extraordinary opportunity to own two parcels in a newly developed beachfront enclave, complete with private entry gates when project is complete leading directly to the pristine sugar sands and turquoise waters of the Gulf of Mexico. Parcel one, identified by property ID 7847700154, offers a 2,000-square-foot homesite with 100 feet of direct Gulf frontage. Parcel two, property ID 78477000078, is a sprawling 9,757-square-foot parcel. These two exclusive Gulf-front estates are nestled at the end of North Gulfside Road on Longboat Key, offering unmatched privacy in a secluded cul-de-sac. With endless views, serene surroundings, and ultimate exclusivity, this is a rare chance to create your dream coastal haven. 6509 is also listed if you would like to have a estate size lot.

LONGBOAT KEY

6601 GULFSIDE ROAD

None Beds

None Baths

0.22 acres

$5,600,000

MLS#: A4685370

A Rare Opportunity to Own an Exquisite Bayfront Property on Longboat Key!
Discover an extraordinary chance to build the waterfront estate of your dreams on this sprawling estate-sized property located in the exclusive enclave of Bayou Hammock. Boasting an impressive 200 feet of direct bayfront access, this prime location offers unobstructed, forever views across the bay to the Intracoastal Waterway.
Immerse yourself in the natural beauty of the surroundings, where panoramic vistas of sparkling water are complemented by the serene sights and sounds of graceful seabirds, playful sea life, and gentle bay breezes. This private, secluded setting provides a rare blend of tranquility and prestige, making it the perfect canvas for a magnificent custom estate.
Whether you envision a grand waterfront mansion, lush tropical landscaping, or a private dock to fully embrace the boating lifestyle, this property offers endless possibilities. Don't miss this once-in-a-lifetime opportunity to secure one of Longboat Key’s most coveted bayfront addresses.
For those who value privacy, elegance, and breathtaking waterfront views, this property represents an unparalleled offering. Walking distance to the beach and many fine restaurants and shopping.

LONGBOAT KEY

6516 BAYOU HAMMOCK ROAD

None Beds

None Baths

0.78 acres

$5,400,000

MLS#: A4632347

#A4703088

LONGBOAT KEY

455 LONGBOAT CLUB ROAD 905

3 Beds

3 Baths

2,880 Sq.Ft.

$5,295,000

MLS#: A4703088

Spectacular Gulf of Mexico views define this exceptional three-bedroom, three-and-a-half-bath residence that lives like a single-family home. A large wraparound terrace with a built-in grill offers seamless indoor-outdoor living, and private steps leading directly to the sandy beach – perfect for sunset entertaining or morning walks along the shore. Enter the home through a private elevator into a formal foyer with double door entry into the residence. The gracious living room is framed by expansive windows showcasing endless water views and exceptional sunsets flowing effortlessly to a built-in wet bar complete with wine refrigerator, ice maker, and a dedicated desk area—ideal for entertaining or casual work-from-home moments. A formal dining room with elegant ceiling detail makes hosting a dinner party a treat. Plantation shutters throughout the residence add a coastal and private touch. The gourmet kitchen is designed for both function and style, offering a large island for gathering, side-by-side Sub-Zero refrigerator and freezer, Wolf gas cooktop, Wolf oven with warming drawer, generous pantry, and a cozy desk area for browsing favorite recipes. A large center island and charming breakfast nook are the perfect spots for morning coffee or casual meals. Adjacent to the kitchen, the inviting keeping room opens to a private east-facing terrace with beautiful sunrise and views of Sarasota Bay. The expansive owner’s suite is a true retreat, featuring its own breakfast bar with sink and refrigerator for enjoying morning coffee while overlooking the Gulf. Two oversized, custom-built walk-in closets provide exceptional storage. The spa-inspired bath includes double vanities, a glass-enclosed shower, a private water closet with bidet, and refined finishes throughout. Two en-suite guest bedrooms with large custom-built closets open onto a private terrace with views of Sarasota Bay, ensuring comfort and privacy for family and guests alike. This rare beachfront residence combines luxury, privacy, and the ease of coastal living, all with breathtaking views and thoughtfully designed spaces for everyday enjoyment and elegant entertainment. Residents of La Firenza enjoy a boutique, gated setting with private beach access, a heated beachfront pool and spa, fitness facilities and secure garage parking.

LONGBOAT KEY

4127 GULF OF MEXICO DRIVE N102

3 Beds

3 Baths

3,521 Sq.Ft.

$4,700,000

MLS#: A4680618

#A4661312

LONGBOAT KEY

569 BAYVIEW DRIVE

6 Beds

4 Baths

4,106 Sq.Ft.

$4,695,000

MLS#: A4661312

#A4666688

LONGBOAT KEY

1571 HARBOR CAY LANE

4 Beds

3 Baths

4,209 Sq.Ft.

$4,550,000

MLS#: A4666688

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