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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

293

# of Listings

2

Avg # of Bedrooms

$1,259

Avg. $ / Sq.Ft.

$2,030,157

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

293 Properties Found. Page 2 of 20.

This spectacular waterfront pool home was just completed in 2026 and is built with uncompromising craftsmanship and every attention to detail. A West Indies-inspired residence in the coveted neighborhood of Emerald Harbor on Longboat Key, it offers expansive water views from every room of the wide canal and Harris Bayou, granting easy access to the intracoastal waterway and the Gulf of Mexico. Walls of glass open to covered porches with remote screens that allow for easy indoor-outdoor living. Features include an incredible chef's kitchen with high-end appliances and a totally separate prep kitchen; Of the 4 bedrooms, there are two primary suites, and all of them have their own stunning en-suites. Each one has access to a covered balcony and all have those stunning water 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 makes this a truly special offering.

LONGBOAT KEY

711 OLD COMPASS ROAD

4 Beds

4 Baths

4,274 Sq.Ft.

$6,495,000

MLS#: A4699408

Introducing Maison d’Azur, a custom waterfront estate in the prestigious Hideaway Bay enclave on the north end of Longboat Key. WHERE COASTAL LUXURY LIVING MEETS THE BAY! This exquisite four-bedroom, five-bath Key West-inspired residence, crafted by acclaimed builder John Cannon, seamlessly blends indoor and outdoor living to create an atmosphere of refined luxury reminiscent of a boutique hotel. Situated on over a quarter of an acre, this bayfront property commands breathtaking, unobstructed views. Enjoy the vibrant hues of sunrise and sunset over tranquil waters, with palm fronds swaying in the coastal breeze.

With a newly renovated private forty-foot-deep water dock and boat lift, Maison d’Azur is a haven for boat enthusiasts and nature lovers. Spend afternoons in the saltwater pool and evenings on the loggia as the Belt of Venus rises over Sarasota Bay. Enjoy dining from your custom outdoor kitchen, surrounded by lush tropical landscaping. Step inside to experience luxury and meticulous craftsmanship, with a grand foyer featuring soaring ceilings and custom pillars. The open floor plan connects a chef’s kitchen, equipped with Sub Zero, Miele, Fisher and Paykel, and Wolf appliances, to a spacious family room with built in cabinetry, creating an inviting atmosphere for entertaining. Archways lead to elegantly decorated formal dining and living rooms.

Ascend the private elevator to the second floor, where a great room with a custom entertainment center awaits, along with a study perfect for savoring a cognac on the captain’s porch. The expansive second floor offers a loggia and bedrooms with stunning panoramic views of the pool and Sarasota Bay. Maison d’Azur embodies exquisite taste and timeless beauty. With imported materials and innovative technology throughout, every detail has been curated for an elegant experience. This residence is sold fully furnished, with pieces selected to enhance each room’s design and ambiance.

Hideaway Bay is located on Longboat Key, an eleven-mile island off the coast of Sarasota. This enclave of only seventeen estates is steps away from the deeded beach and boasts two private tennis courts. Residents enjoy easy access to premier country clubs, golf courses, waterfront activities, dining options, and upscale shopping. Experience coastal living where every day feels like a vacation amidst the beauty and tranquility of the Gulf Coast. This property sustained no damage from the storms/hurricanes of last year. It boasts an elevation of 10.5’, ensuring you stay high and dry.

LONGBOAT KEY

757 HIDEAWAY BAY DRIVE

4 Beds

5 Baths

4,507 Sq.Ft.

$6,295,000

MLS#: A4667459

Rarely does a Gulf-front residence of this caliber become available within Aria, an ultra-exclusive enclave of just 16 residences on Longboat Key. Set along 300 feet of private shoreline, this extraordinary property offers an exceptional opportunity to experience true beachfront luxury in one of Sarasota’s most sought-after communities, complete with a newly added video tour. Beyond the gated entrance, Aria unveils a serene setting with lush native landscaping, tranquil walking paths, and the historic Villa am Meer, a beautifully restored 1935 seaside mansion serving as the community’s social centerpiece. Spanning nearly 4,000 square feet, this residence is accessed via a private elevator opening to a grand foyer and expansive, light-filled interiors with newly refreshed cabinetry throughout. The open-concept floor plan seamlessly connects living and dining spaces with a gourmet chef’s kitchen equipped with quartz surfaces and top-tier Wolf and Miele appliances. Walls of floor-to-ceiling glass and soaring ceilings capture sweeping Gulf views, while expansive wraparound terraces offer the perfect backdrop for sunsets and coastal breezes. The primary suite serves as a luxury sanctuary with dual baths connected by a rare, oversized walk-in shower, complemented by two guest ensuite bedrooms, a dedicated office or fourth bedroom, and a versatile bonus room. This residence includes a private, oversized two-car dehumidified garage, with access to Aria’s beachfront pool and spa, fitness and yoga studios, massage room, private wine cellar, and full-time onsite caretaker.

LONGBOAT KEY

2251 GULF OF MEXICO DRIVE 301

4 Beds

4 Baths

3,921 Sq.Ft.

$5,999,000

MLS#: A4658325

#A4691731

LONGBOAT KEY

530 JESSMYTH DRIVE

None Beds

None Baths

0.28 acres

$5,985,000

MLS#: A4691731

Price reduced

Private island home for sale on Jewfish Key, Longboat Key, Florida. This 4-bedroom, 4-bath waterfront residence sits on a 1.24-acre titled lot with approximately 300 feet of water frontage and a private deep-water dock, and it is reached only by boat. It is one of just eight homes on this roughly 38-acre island at Longboat Pass. 7143 La Lenaire Drive is offered turnkey and furnished, and it is on the market for the first time in more than two decades.

Reached only by boat, this private island home offers something rare on Florida's coast: luxury, privacy, and room to truly disconnect. Far from crowded waterfront rentals, it's a place to slow down, enjoy the people you came with, and share an experience your family and friends will never forget.

The home was custom built in 2011 and has more than 2,700 square feet of living space, designed around sweeping west-facing water views and easy indoor-outdoor living. The main living areas open to covered outdoor space overlooking the Intracoastal Waterway, and at sunset the evening light fills the rooms. The layout works as well for a quiet weekend for two as it does for a full house of guests.

Walk down to your own deep-water dock, with direct boating access to Sarasota Bay, the Intracoastal, Longboat Pass, and the Gulf. Anna Maria Island, Longboat Key, and St. Armands Circle are minutes away by water, so Sarasota and Bradenton dining, shopping, beaches, and culture are easy to reach while your evenings stay quiet and private.

Jewfish Key is surrounded by sandbars, clear shallows, native wildlife, and natural shoreline, a setting that is increasingly hard to find along the Gulf Coast. This property works as a primary residence, a private Florida vacation home, or an income-producing investment. With four bedrooms, four baths, and a boat-access location unlike anything else on the rental market, it offers strong short-term and seasonal rental potential for investors seeking a one-of-a-kind luxury waterfront asset between Longboat Key and Anna Maria Island.

Schedule your private boat tour today.

LONGBOAT KEY

7143 LA LENAIRE DRIVE

4 Beds

4 Baths

2,721 Sq.Ft.

$5,895,000

MLS#: A4694196

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

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

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

Set against the luminous backdrop of prestigious Longboat Key, this newly built residence offers a quietly sophisticated interpretation of island living. Ideally situated just across from the beach, the home is framed by glimpses of the water, while its considered architecture and refined interiors create an atmosphere of understated luxury. Here, contemporary design meets the effortless beauty of coastal life, creating a private retreat that feels polished yet deeply connected to its surroundings. Lush, mature landscaping envelops the property in a verdant embrace, ensuring privacy and a sense of tranquility that makes every moment feel like a serene escape. Sunlight streams through expansive windows, filling every room with natural light and creating an inviting atmosphere. Featuring a 3-car garage with dual driveways and convenient elevator access to all levels, the impressive 4,361-square-foot residence, with a total of 6,527 square feet under roof, is thoughtfully designed for both grand entertaining and intimate daily living. An attached poolside casita boasts a dedicated entrance with elegant French doors, a bedroom with a walk-in closet, a kitchenette, a full bath, and a covered lanai. Every detail has been carefully considered to ensure comfort and versatility, with 4 additional bedrooms, 3.5 baths, a quiet study, an upper-level lobby and exercise room, plus laundry rooms on both floors for ultimate convenience. Step inside through grand iron-and-glass double doors to a dramatic foyer and gallery, where a stunning glass-enclosed wine room is an artistic focal point. High ceilings amplify the airy, light-filled ambiance throughout, creating a sense of openness and grandeur that is both welcoming and awe-inspiring. The screened pool area features a rejuvenating spa, tranquil waterfall, captivating fire feature, and an expansive covered lanai with a built-in cabana bar, professional-grade grilling station, serving-island buffet, generous dining space, and a comfortable outdoor living area. Inside, the great room impresses with a sleek linear fireplace, beautifully designed beamed ceiling, and massive glass sliders that open wide to the lush poolside retreat. The high-end island kitchen is a connoisseur's dream, equipped with premium appliances and a wall of windows framing vibrant tropical views. Adjacent spaces include a pool bath, a large walk-in pantry, a laundry room with a sink and ample storage, and a convenient elevator valet area. The study is a private haven, featuring a custom ceiling, two full walls of glass with panoramic views, and a VIP ensuite off the foyer with a secluded balcony for peaceful moments. Distinctive designer light fixtures and dazzling chandeliers lend the space glamour and sophistication. Upstairs, the second floor includes elevator access, a lobby, an exercise room, two bedrooms, and a full bath. A dramatic bridge overlooking the great room leads to the magnificent primary suite, with intricate ceiling details, a large expanse of windows, a private water closet, a spa-like bath with dual vanities, a freestanding soaking tub, a grand full-height glass shower, and a customized wardrobe room. Completed in December 2025 by custom luxury builder John Cannon Homes, this exceptional residence is far more than a stylish, elegant home with gracious open living—it is a sanctuary, a retreat, and an invitation to savor the very best of the coastal lifestyle.

LONGBOAT KEY

3100 GULF OF MEXICO DRIVE

5 Beds

5 Baths

4,361 Sq.Ft.

$5,295,000

MLS#: A4707515

#A4694394

LONGBOAT KEY

3606 FAIR OAKS PLACE

5 Beds

3 Baths

3,842 Sq.Ft.

$4,999,000

MLS#: A4694394

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

#A4707025

LONGBOAT KEY

3360 BAYOU SOUND

5 Beds

4 Baths

4,000 Sq.Ft.

$4,699,999

MLS#: A4707025

Price reduced

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. The owner will consider a lease purchase with acceptable terms on this residence.

LONGBOAT KEY

1591 GULF OF MEXICO DRIVE 413

2 Beds

2 Baths

2,154 Sq.Ft.

$4,409,000

MLS#: A4627935

#A4666688

LONGBOAT KEY

1571 HARBOR CAY LANE

4 Beds

3 Baths

4,209 Sq.Ft.

$4,400,000

MLS#: A4666688

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