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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

417

# of Listings

2

Avg # of Bedrooms

$1,122

Avg. $ / Sq.Ft.

$2,032,790

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

417 Properties Found. Page 4 of 28.

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

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

2,154 Sq.Ft.

$4,499,000

MLS#: A4627935

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

1,173 Sq.Ft.

$4,499,000

MLS#: A4669533

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

4,044 Sq.Ft.

$4,424,000

MLS#: A4661988

DIRECT BEACH FRONT WALKOUT !! Completely redone in 2024!!The west facing private terrace off the living room and master bedroom has the exclusive feature of a Gulf front terrace with a private staircase that leads directly to the sandy beach and azure waters of the Gulf of Mexico. This rarely available floor plan is a stunning residence with front and back terraces. The east private terrace captures vistas of the beautiful sunrises and the west terrace looks over the beach to the Gulf of Mexico plus spectacular evening sunsets. This home is both casual and elegant. The floor plan offers two bedrooms and a third room as an office or a bedroom with a full bath nearby. The Gulf front master has spectacular views plus a sliding door that leads to the large terrace. The master suite features ample closet space plus his and her private bath areas. L' Ambiance amenities include a concierge in the lobby, 24 hour guard gate for security and an Olympic size Gulf side pool surrounded by lush landscaping. Other amenities include two har-tru tennis courts, state-of-the-art fitness center with his and her locker rooms, game and billiard rooms, library, wine room and three private guest suites. This condo has two underground parking spaces plus a private storage locker. The location of L'Ambiance is minutes away from the shopping and dining on St.Armands Circle plus walking distance to Longboat Key Club restaurants and amenitie

LONGBOAT KEY

415 L AMBIANCE DRIVE C204

3 Beds

3 Baths

2,800 Sq.Ft.

$4,395,000

MLS#: A4636316

Significant price improvement on this beautifully maintained canal home in Country Club Shores, one of Longboat Key’s premier waterfront communities. This solid-block residence offers 4,438 sq. ft. of bright, open living with wide sailboat-water canal views and a layout ideal for full-time or seasonal living.

Enjoy a spacious chef’s kitchen, generous living areas, and comfortable bedroom suites. The outdoor space features a private pool, tropical landscaping, and a deep-water dock with quick access to Sarasota Bay and the Gulf.

Perfectly located near deeded beach access, the Longboat Key Club, the new St. Regis Longboat Key Resort, and the shops and dining of St. Armands Circle. Downtown Sarasota is minutes away, offering world-class arts and culture. A refined opportunity in one of Longboat Key’s most desirable neighborhoods.

LONGBOAT KEY

524 SCHOONER LANE

4 Beds

4 Baths

4,438 Sq.Ft.

$4,300,000

MLS#: A4648699

Spectacular Gulf front location! Rarely available A floorpan Three bedroom, three bath direct beach corner residence with southern exposure with vistas to the beach, azure Gulf waters and sunsets plus views of the Longboat key Club golf course, Sarasota Bay and downtown Sarasota lights. Sunrise, sunsets are all enjoyed from this third floor spacious, open floor plan. A private, secured elevator opens to the interior of the residence while a separate elevator brings guests to the front door. Special features of this luxurious residence include 10' foot ceilings, floor to ceiling sliding glass doors, 8' solid mahogany doors plus porches on east and west side of this 3400 sq.ft. home. The kitchen has a wonderful center island plus a breakfast room. The master suite has expansive walls of windows enhancing the gulf views. The master bath is appointed with marble floors and walls, dual vanities and spa tub. Regent Place offers 24 hour security, a 25 -meter heated pool and spa overlooking the Gulf, summer kitchen by the pool, club house with social room and fitness center.

LONGBOAT KEY

675 LONGBOAT CLUB ROAD 23A

3 Beds

3 Baths

3,564 Sq.Ft.

$4,195,000

MLS#: A4648954

New on site 2 days ago

#A4677813

LONGBOAT KEY

795 MARBURY LANE

4 Beds

3 Baths

3,355 Sq.Ft.

$3,999,990

MLS#: A4677813

Price reduced

GULF AND BAY VIEWS! THREE OUTDOOR PATIOS! Discover an extraordinary coastal contemporary masterpiece by Floridian Crafted Homes, perfectly positioned on Longboat Key with breathtaking Gulf and Bay views. This 13 FEET ELEVATED, hurricane-fortified residence offers 5 bedrooms, 5 full bathrooms, and 2 partial bathrooms across 4,176 square feet of luxurious living space. Home has elevator shaft blocked in and ready to receive elevator mechanics. Designed for both elegance and functionality, this home features three expansive outdoor living spaces, including two private balconies and a stunning rooftop deck, perfect for capturing the serene Gulf sunsets. The open-concept great room flows effortlessly into the gourmet kitchen, creating an entertainer’s dream, while the second-floor club room offers a private retreat for relaxation. Outdoors, a private pool and spa provide a tranquil escape, while the 5+ car garage ensures ample storage for vehicles and beach essentials. Located just steps from the beach and steps to the upcoming retail and dining destination (Est. Fall 2025), this home also offers access to a community marina with available boat slips, making it ideal for boating enthusiasts. Experience the pinnacle of modern coastal luxury in this exceptional Longboat Key residence—where timeless design, breathtaking views, and an unparalleled location create the ultimate island retreat.

LONGBOAT KEY

597 BUTTONWOOD DRIVE

5 Beds

5 Baths

4,176 Sq.Ft.

$3,999,950

MLS#: A4640902

ELEVATED Waterfront Luxury on Longboat Key! Welcome to 550 Yardarm Lane, where the elegance of Longboat Key meets the ease of Florida’s coastal lifestyle in the coveted Country Club Shores. This waterfront masterpiece isn’t just a home, it’s your front-row seat to paradise, where boating, beach walks, and year-round sunshine are part of everyday life. Step inside and be instantly captivated by sparkling water views, soaring spaces, and the perfect blend of casual comfort and refined luxury. Designed for both relaxation and unforgettable entertaining, this 5-bedroom, 5.5-bath retreat is tailor-made for hosting family and friends in style. PRIME WATERFRONT LIVING - Private dock on a deep-water canal with no-bridge access to the bay, perfect for your weekend cruiser. LIGHT & BRIGHT OPEN LAYOUT - Walls of glass bring the outdoors in, filling the home with sunshine and stunning water views. ELEVATOR - Effortless access to main living levels from the three car garage. CHEF’S DREAM KITCHEN - High-end appliances, custom cabinetry, and an oversized island ready for gourmet meals and lively gatherings. LUXURIOUS SUITES - Owner’s retreat with a private balcony, spa-inspired bath, and dual walk-in closets. MOVIE ROOM - Your own private theater for cozy nights in. OUTDOOR OASIS - infinity pool, spacious patio, and lush landscaping for poolside lounging or sunset soirees. All this just steps to your DEEDED BEACH ACCESS and minutes from the world-class dining, shopping, and cultural treasures of St. Armands Circle and Downtown Sarasota. Whether you’re dreaming of a full-time Florida home or a seasonal escape, 550 Yardarm Lane delivers the ultimate Longboat Key lifestyle.

LONGBOAT KEY

550 YARDARM LANE

5 Beds

5 Baths

4,281 Sq.Ft.

$3,995,000

MLS#: A4672604

This exquisite two-story waterfront home located in the coveted Harbor section of Bay Isles has been meticulously renovated to embody modern elegance and luxurious coastal living. Surrounded by lush tropical landscaping, the home welcomes you through an elegant French door entrance into the grand foyer, where soaring ceilings, gleaming travertine flooring, and a striking wrought iron floating staircase with rich, dark wood steps set the tone for the refined elegance that unfolds throughout the home. The lower level boasts a bright and airy open space with hardwood floors throughout, creating a welcoming atmosphere that effortlessly combines sophistication with the timeless beauty of natural materials. The spacious family room is anchored by a stunning fireplace with decorative columns and an elegant mantel, complemented by French doors leading to the expansive waterfront lanai, reinforcing the home's seamless connection to its stunning natural surroundings. A culinary enthusiast’s dream, the generously sized kitchen features a large island with a waterfall granite countertop, custom cabinetry, ample storage space, and high-end stainless steel appliances, including a six-burner gas range and double ovens. Adjacent to the kitchen, the dining area and great room spaces flow seamlessly into each other. The great room is both grand and inviting, showcasing a dramatic wood-clad cathedral ceiling that adds warmth and character. A second stone fireplace enhances the ambiance, while three sets of French doors that open onto the lanai offer an effortless transition between indoor and outdoor living. Also on this level are two generous guest suites, each with a full bath, one with direct lanai access, and a den with full bath. Upstairs, the primary suite is a true retreat. Floor-to-ceiling windows illuminate the space, and French doors open to a spacious private balcony, offering captivating water views that create a peaceful escape. A cozy fireplace adds to the intimate atmosphere, while the spa-inspired en-suite bath indulges with marble flooring, soaking tub, dual vanities, frameless glass walk-in shower, and water closet, all overlooking the serene waterway. The outdoor living space is equally spectacular, designed for both relaxation and entertaining. The expansive lanai features multiple covered areas with a rich wood-clad ceiling and retractable screens, a sun-drenched open-air section, and a stunning saltwater pool with travertine decking framed by verdant tropical landscaping. Just beyond the pool, a private dock with a boat lift sits on a deep-water basin and wide canal with no bridges to Sarasota Bay, offering quick and direct access for boating enthusiasts. Bay Isles Beach Club membership is included. This extraordinary home seamlessly blends elegance, comfort, and the unparalleled beauty of waterfront living, creating a sanctuary that is as functional as it is breathtaking.

LONGBOAT KEY

520 HARBOR CAY DRIVE

4 Beds

4 Baths

3,828 Sq.Ft.

$3,995,000

MLS#: A4643565

Discover an exceptional opportunity to live behind the gates of the Longboat Key Club in the highly coveted Corey’s Landing neighborhood — one of the island’s premier bayfront addresses. Set within an intimate, established enclave of just 61 single-family homes and villas, this free-standing residence welcomes you through double doors into a showplace of light, style, and space. Step outside to the expansive screened lanai — an inviting oasis for relaxing or entertaining by the pool while taking in mesmerizing bay views and the twinkling lights of downtown Sarasota. Enjoy immediate bay access with the private boat dock and lift. Inside, soaring transom windows, walls of glass, and rich wood floors enhance the open great-room design — a perfect setting for entertaining around the elegant fireplace. The updated kitchen connects seamlessly to the dining and living areas, showcasing sleek white cabinetry, a striking tile backsplash, solid-surface countertops, stainless steel appliances, and a generous breakfast bar ideal for casual gatherings. The first-floor primary suite is a private retreat with walls of glass, a cozy sitting area, custom built-ins, dual closets, and a luxurious remodeled bath featuring dual vanities, a large walk-in shower, and a separate water closet. Also on the main level are a private guest suite, second bedroom, full bathroom, a study/den, and a convenient outdoor dog space. Upstairs, a versatile loft provides the flexibility for a gym, library, or additional guest accommodations. The attached two-car garage offers ample storage, while Corey’s Landing residents enjoy access to a community pool, spa, Har-Tru tennis courts, and the private Bay Isles Beach Club. Ideally located near world-class shopping, dining, and the renowned St. Armands Circle, this residence captures the essence of the Longboat Key lifestyle — elegant, relaxed, and effortlessly connected to both land and sea.

LONGBOAT KEY

3488 MISTLETOE LANE

3 Beds

3 Baths

3,341 Sq.Ft.

$3,980,000

MLS#: A4670010

#A4676754

LONGBOAT KEY

3540 MISTLETOE LANE

4 Beds

3 Baths

3,166 Sq.Ft.

$3,595,000

MLS#: A4676754

New on site 4 days ago

Welcome to an extraordinary corner residence at The Water Club where timeless elegance meets effortless coastal living on Longboat Key. Offering 3,275 square feet of beautifully designed interior space, this 3-bedroom, 4.5-bath condominium captures sweeping unobstructed expansive views of the Gulf of Mexico, glowing sunsets, Sarasota Bay, and the city skyline from nearly every room. Floor-to-ceiling windows and expansive sightlines fill the home with natural light, creating a serene and sophisticated atmosphere throughout. Designed with refined craftsmanship, the residence showcases custom woodworking, hardwood floors, and soaring 10-foot ceilings that enhance the sense of scale and luxury. The thoughtfully designed layout provides generous living and entertaining spaces while maintaining privacy for guests. The home is in true move-in condition and has been thoughtfully updated with all-new appliances in 2025, blending modern convenience with classic finishes. Enjoy the exclusivity of private elevator access directly to the residence, along with full concierge services that elevate everyday living. The building offers an impressive collection of resort-style amenities, including a Gulf-front swimming pool overlooking pristine white sand beaches, a fully equipped fitness studio, an elegant library, a grand ballroom for entertaining, and a game room for relaxation and recreation, a premier parking space, and as well as climate controlled storage units. This exceptional property delivers the best of beachfront living with luxury, privacy, and breathtaking views all within one of Longboat Key’s most desirable addresses. A rare opportunity to own a refined coastal retreat where every detail has been carefully considered and every day feels like a getaway.

LONGBOAT KEY

1281 GULF OF MEXICO DRIVE 708

3 Beds

4 Baths

3,273 Sq.Ft.

$3,595,000

MLS#: A4677632

St. Regis Longboat Key offers an exceptional opportunity to experience refined living on the pristine sands of Longboat Key. This distinguished five-star resort hotel and private residence enclave commands panoramic views of the Gulf and provides direct beach access, setting the stage for an unparalleled coastal lifestyle.
Upon entering this remarkable residence, one is immediately welcomed by voluminous ceiling heights and expansive views that infuse the interiors with abundant natural light. The thoughtful architectural design ensures breathtaking water vistas from the kitchen, oversized balcony, great room, and dining area, creating an ambiance of openness and serenity. The kitchen, equipped with premium Wolf and Sub-Zero appliances, is a testament to both performance and sophistication, perfectly suited for culinary enthusiasts.
The primary bedroom suite seamlessly extends into a generous walk-in closet and a luxurious bathroom, complete with a frameless walk-in shower, mechanized commode, and his and her sinks. For ultimate convenience and security, residents may enjoy direct elevator access to their home via keyless entry, setting a new standard in modern elegance.
Beyond the residence itself, St. Regis Longboat Key presents a distinguished array of amenities meticulously curated for its residents. The Private Resident’s Clubhouse offers an environment of exclusivity, complemented by a state-of-the-art fitness center, as well as a pool and spa area reserved solely for residential use. Residents are granted privileged access to the legendary St. Regis Butler and Concierge services, which exemplify world-class hospitality and attention to detail.
An extraordinary oceanfront spa awaits, alongside diverse dining experiences that showcase the highest standards of culinary excellence. Personal cabanas along the shore create private retreats for relaxation, while the family-friendly amenities include a meandering lazy river and a unique saltwater lagoon. This lagoon is home to a vibrant array of tropical fish species, graceful stingrays, and the resort’s resident tortoises, offering a captivating wildlife experience within the lush grounds.
Spanning seventeen acres of beachfront on the coveted Longboat Key barrier island, this private oasis is conveniently located only 3.5 miles from St. Armand’s Circle, the region’s premier destination for shopping and dining. Whether seeking tranquil solitude or an active social environment, every aspect of life at St. Regis Longboat Key has been thoughtfully designed to anticipate and fulfill the desires of its residents.
This offering represents more than just a residence; it is an invitation to embrace the legendary St. Regis lifestyle, defined by elegance, comfort, and outstanding service. Begin your journey to extraordinary Gulfside living.

LONGBOAT KEY

1581 GULF OF MEXICO DRIVE 507

1 Beds

1 Baths

1,721 Sq.Ft.

$3,500,000

MLS#: A4665165

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