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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 6 of 28.

#A4670192

LONGBOAT KEY

569 ROUNTREE DRIVE

3 Beds

3 Baths

3,428 Sq.Ft.

$3,190,000

MLS#: A4670192

Prepare to be wowed by the direct turquoise Gulf views from the oversized wraparound terrace, main living areas and primary bedroom. The chef’s kitchen is open to the main living area and offers state-of-the-art JennAir stainless steel appliances complete with built-in convection and steam ovens, oversized center island, wine refrigeration with storage and breakfast area. The massive primary suite showcases floor to ceiling windows with the same big Gulf views, access to the terrace, garden tub with separate shower and two walk-in closets. The main guest bedroom is ensuite with its own private terrace access and another walk-in closet. The 3rd bedroom is being used as a den with French doors opening to the living room, its own ensuite full bath with shower and dazzling Gulf views. Other bonus rooms include a laundry room located conveniently off the kitchen with sink, and an office nook with built-ins adjacent to the foyer. This residence comes with TWO under building parking spaces and a separate storage locker. Located behind the prestigious gates of The Longboat Key Club on the desirable South end of Longboat Key, owners will enjoy being minutes from the fine dining and shopping on St. Armands Circle in addition to the close proximity to Southwest Florida’s cultural hub of downtown Sarasota. At the Sanctuary, you will be part of 18 incredible beachfront acres with trails, an Olympic sized heated pool and spa, lighted tennis courts, a fitness center, onsite management, 24-hour manned security gate and a club house with planned activities. Become a member of the Longboat Key Club and partake in the superior golf courses, 6 private restaurants, spa and wellness center and other AAA four-diamond beach resort offerings. Roof replaced in 2023, Elevators modernized in 2022, and pool decking replaced in 2024. Building passed the Milestone Structural Integrity Inspection.

LONGBOAT KEY

545 SANCTUARY DRIVE B204

3 Beds

3 Baths

3,115 Sq.Ft.

$3,150,000

MLS#: A4667288

Tucked within the private enclave of the Longboat Key Club, this beautifully reimagined penthouse at The Pierre offers an inspired blend of Manhattan sophistication and relaxed coastal charm. This three-bedroom, three-and-a-half-bath residence has been fully renovated to perfection, showcasing a fresh, contemporary design with sleek finishes, designer lighting, and open, airy living spaces that capture mesmerizing views of the golf course, Sarasota Bay and downtown Sarasota. Expansive balconies invite you to unwind and take in the breathtaking scenery, creating a seamless connection between indoor elegance and outdoor tranquility. The resort-style amenities elevate everyday living: a 24-hour concierge, two secured garage parking spaces, private storage locker, a heated pool, shuffleboard, two Har-Tru tennis courts, fitness center with sauna, and an outdoor grilling area and gazebo. Enjoy deeded beach access for tranquil mornings by the Gulf or host guests in one of three well-maintained guest suites offered at a nominal rate. With on-site management and a financially strong association, peace of mind comes standard. This is the definition of penthouse elegance.

LONGBOAT KEY

455 LONGBOAT CLUB ROAD PH8

3 Beds

3 Baths

2,780 Sq.Ft.

$2,999,999

MLS#: A4671740

#A4676878

LONGBOAT KEY

510 PUTTER LANE

3 Beds

2 Baths

2,253 Sq.Ft.

$2,999,000

MLS#: A4676878

Introducing an exceptional beachfront residence that redefines luxury living on Longboat Key, offering panoramic seventh-floor views that span from the Gulf of Mexico to Sarasota Bay. This beautifully furnished three-bedroom, four-bath retreat encompasses over 3,000 square feet under air and delivers an unparalleled coastal lifestyle. The expansive great room is elegant and versatile, featuring a built-in library display and direct access to the main balcony, ideal for entertaining or quiet relaxation. The gourmet kitchen is a chef’s delight, complete with white cabinetry, stone countertops, a center island, a new refrigerator and a cozy breakfast nook with captivating views of the beach. The primary suite is a private sanctuary, offering a spacious walk-in closet, dual baths, and a secluded beachfront terrace for peaceful morning coffee or stunning sunsets. On the opposite side of the residence, a deluxe en-suite guest room with a large walk-in closet awaits, along with a flexible third bedroom, office, or den with a full bath conveniently across the hall. A semi-private elevator delivers you directly to your home and connects you to the resort-style amenities that make Water Club one of Longboat Key’s most prestigious addresses with impeccable concierge service, an 18,000-square-foot clubhouse with fitness center, spa, library, game room and ballroom, a heated beachfront pool and spa, fire pit courtyard and Har-Tru tennis courts, all with 24-hour gated security for ultimate peace of mind. On 16 acres of lush tropical landscaping and boasting 680 feet of private beachfront, Water Club offers an exceptional blend of privacy, luxury and community. Pet-friendly and well located, you’re just minutes from world-class golf, boating, boutiques, dining and the cultural heartbeat of downtown Sarasota. Experience the pinnacle of coastal elegance—where every day is a celebration of Longboat Key’s natural beauty and refined lifestyle.

LONGBOAT KEY

1281 GULF OF MEXICO DRIVE 704

3 Beds

4 Baths

3,054 Sq.Ft.

$2,995,000

MLS#: A4666680

Savor the panoramic views and never-ending sunsets from this 7th-floor corner condominium, where the Gulf of Mexico, Sarasota Bay, downtown’s cityscape, and the manicured grounds of the Longboat Key Club’s Islandside golf course unfold in every direction. Elegant L’Ambiance is located on the southern end of Longboat Key, and the community entrance is adorned with water fountains, artistic creations, and has a 24hr manned gate leading to a secured building with a full-time concierge dedicated to attend to you and your every need. The elevator will take you to a private foyer leading directly into the residence. Here you’ll find lovely details such as a pecky cypress foyer ceiling, a dry bar, living room built-ins, cove lighting, expansive terraces, and never-ending views. The unit has two bedrooms, two and one-half baths, a full-sized laundry room and a back service entrance. The kitchen sports a center island and a breakfast nook with direct access to the expansive terrace. The main living area is open and spacious, filled with natural light with sliding doors open to the wraparound terrace. A split bedroom plan ensures privacy for you and your guests. Take in the gulf views from the primary bedroom suite, which has been recently enhanced with an extra-large closet. There is the added convenience of motorized blinds and drapes throughout. This gorgeous apartment comes with a private parking space, a storage unit and a wine locker. Other amenities include a luxurious beach-side pool with waterfalls, two har-tru tennis courts, a finely equipped fitness center, social rooms, guest parking, guest suites, and direct beach access. Living on Longboat Key, one of Florida’s most desirable areas, means more than a home — it’s a lifestyle. From the pristine beaches and world-class golf and tennis (membership required) to boutique shopping, fine dining, and cultural attractions just minutes away in Sarasota, you’ll enjoy the perfect balance of island tranquility and vibrant city life.

LONGBOAT KEY

435 L AMBIANCE DRIVE L707

2 Beds

2 Baths

2,525 Sq.Ft.

$2,995,000

MLS#: A4663998

Price reduced

Exquisite Gulf-Front Residence at L’Ambiance. Presenting a truly rare opportunity—this direct Gulf-front 2-bedroom plus den residence offers the pinnacle of beachfront living at the L’Ambiance on Longboat Key. Featuring the coveted Sabal floor plan, this thoughtfully designed home boasts both sunrise and sunset terraces. Start your mornings with serene eastern light and end your day with sweeping, unobstructed views of the Gulf from your expansive western terrace. Effortlessly blending refined coastal style with luxurious finishes, the residence offers a spacious layout with two bedrooms and a versatile third space—ideal for a home office or guest room—paired with a nearby full bath. The Gulf-front primary suite is a peaceful retreat with panoramic water views, direct terrace access, abundant closet space, and dual bathrooms designed for privacy and comfort. L’Ambiance is Longboat Key’s premier beachfront community, offering an exceptional lifestyle with a 24-hour staffed gatehouse and full-time concierge, a resort-style beachfront pool surrounded by lush tropical landscaping, and two Har-Tru tennis courts. The state-of-the-art fitness center includes his and her locker rooms, and residents enjoy access to game and billiard rooms, a wine room, and a private library. Three elegantly appointed guest suites are available for visiting friends and family.
Additional highlights include secured underground parking, a private storage locker, and an unbeatable location just moments from the shops and dining of St. Armands Circle. The residence is also within reasonable walking distance to the Longboat Key Club’s acclaimed restaurants and resort amenities. This is beachfront living at its most luxurious—an extraordinary coastal retreat that rarely becomes available.

LONGBOAT KEY

415 L AMBIANCE DRIVE D306

2 Beds

2 Baths

2,634 Sq.Ft.

$2,995,000

MLS#: A4649174

Seller has reduced price for immediate sale. Rare opportunity to be a resident at The St. Regis Longboat Key for under $3,000,000. Enter your private elevator into a dramatic living area with high ceilings and expansive glass featuring spectacular views of Sarasota Bay. The living area opens to a large outdoor terrace with a Wolf gas grill for easy entertainment. The chef’s kitchen is equipped Poggenpohl cabinetry, top-of-the-line Wolf and Sub-Zero appliances, including a gas cooktop, double ovens, microwave, large refrigerator and beverage center. If you don’t feel like cooking, just order room service from one of The St. Regis’s esteemed dining venues. The Earth finishes were curated by Marc Michales Interior Design and were selected to remain timeless. The owner’s suite is luxurious and opens to the outdoor terrace for your morning coffee. Relax after a day at the beach or saltwater lagoon in the spa like bathroom boasting double vanities, water closet with Toto bidet toilet, soaking tub and oversize shower with seamless glass enclosure. The floor plan was altered to include two full bathrooms and is large enough to graciously accommodate overnight guests. 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 allure of a seaside getaway. 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. Resident only amenities include a clubhouse, fitness center, pool/spa and beach area. Enjoy your private resident only amenities, while having access to all the resort has to offer. Live like you are on vacation all year round!

LONGBOAT KEY

1591 GULF OF MEXICO DRIVE 515

1 Beds

2 Baths

1,556 Sq.Ft.

$2,970,000

MLS#: A4628048

Great opportunity to build on a private Cu-de-sac in Sleepy lagoon. There is private sandy beach access leading to the azure waters of the Gulf of Mexico. A new home at this location would have outstanding Gulf and stunning sunset views. This Cul-de-sac location is quite and peaceful and the perfect spot for a dream beach home.This location on Gulfside Road offers a unique opportunity to live on a quite loop beachside of Gulf of Mexico Drive. You will enjoy walking this beach and watching the amazing wildlife. This north Longboat location is near many outstanding restaurants and Anna Maria Island.

LONGBOAT KEY

6605 GULFSIDE ROAD

None Beds

None Baths

0.35 acres

$2,900,000

MLS#: A4646914

Experience island living at its finest in this exquisite coastal retreat in the historic Village on Longboat Key. This home offers a refined blend of relaxed coastal charm and timeless sophistication throughout more than 3,300 heated square feet. The meticulously designed interior includes elegant crown molding, coffered ceilings, custom doors, impact windows and an elevator from the garage to each level. The great room features dramatic ceiling height and opens to a large covered terrace overlooking an exceptionally private backyard, creating an ideal setting for quiet evenings and effortless entertaining. The gourmet kitchen is a chef’s dream with rich wood cabinetry, granite countertops, natural gas cooktop, a pot filler, center island with sink and second cooktop, and a bright breakfast nook that opens to a covered terrace, ideal for morning coffee. Adjacent dining and living areas flow seamlessly and are enhanced by a coffered ceiling and French doors to the charming terrace. The second-level primary suite serves as a serene retreat with polished wood floors, an intricate coffered ceiling, a comfortable seating area, and a private covered balcony for enjoying peaceful moments under the morning or evening sky. Elevated views and sound of ospreys add to the sense of tranquility. The suite also features a spacious en-suite bath with soaking tub and two walk-in closets. Three additional bedrooms provide comfort and flexibility for guests or work needs. Outdoors, a resort-style saltwater pool and spa with integrated features are surrounded by lush landscaping and generous lounging space. The expansive ground-floor lanai and outdoor kitchen further enrich the indoor-outdoor living experience. A circular brick drive accommodates more than 10 vehicles, and the oversized two-and-a-half-car garage and first-level area offer abundant storage, ideal for bicycles, golf carts, kayaks and more. The home and pool are centered on a 12,000-square-foot lot, and an adjacent 6,000-square-foot parcel is also available from the same owner for those interested in expanding or creating a larger compound. This unique golf cart friendly community is surrounded by waterfront restaurants, quaint shops, cafés, fitness centers, fishing piers, a boat ramp on Sarasota Bay, kayak launch areas and a pristine Gulf beach just moments away with no mandatory HOA. We invite you to experience this remarkable home in person to fully appreciate its beauty and lifestyle.

LONGBOAT KEY

651 BROADWAY STREET

4 Beds

3 Baths

3,320 Sq.Ft.

$2,899,000

MLS#: A4672952

New on site 2 days ago

Situated within the gated Queens Harbour enclave of Bay Isles, this thoughtfully updated four-bedroom courtyard residence offers a refined blend of privacy, comfort, and waterfront living on Longboat Key. Designed around a lush central courtyard, the home creates an effortless indoor-outdoor flow anchored by a resurfaced swimming pool and new paver deck—an inviting retreat for everyday living or entertaining.

A private cabana suite with its own entrance provides flexibility for guests or extended stays, enhancing the home’s functionality while maintaining separation from the main living areas. Entry begins through custom mahogany and glass double doors, opening to a reimagined open-concept interior with soaring 14-foot ceilings, wide-plank wood flooring, and carefully curated architectural detail throughout.

The great room is centered around a travertine-encased electric fireplace and framed by walls of windows and glass sliders that capture tranquil lake views and abundant natural light. This space flows seamlessly into the formal dining area, highlighted by a statement chandelier and tongue-and-groove tray ceiling, and continues into the chef’s kitchen—designed as the heart of the home.

The kitchen features a dramatic 14-foot quartz-topped island, custom designer cabinetry by Sarasota Architectural Woodworking, and newer Thermador appliances, including a five-burner gas cooktop, dual built-in ovens, pull-out pantry cabinetry, and a 48-inch stainless sink. Adjacent informal dining and family spaces include aquarium-style glass windows and an oversized wet bar with a full-size wine cooler capable of storing over 100 bottles.

The primary suite, located on the main level, offers a peaceful lakefront setting with French-door access to the patio, custom built-in storage, and a walk-in closet. The spa-inspired bath was recently updated with dual quartz-topped walnut vanities, soaking tub, glass-and-stone shower, and private water closet. Also on the first floor are a versatile study overlooking the courtyard and a bonus room with an attached full bath that can serve as an additional bedroom or media space. The second level is dedicated to a private en-suite guest bedroom.

Queens Harbour residents enjoy access to a heated Olympic-size pool and spa, along with deeded entry to the private Bay Isles Beach Club. Beyond the gates, Longboat Key’s lifestyle amenities are just minutes away, including the Longboat Key Club’s golf and tennis facilities, marinas, dining, and everyday conveniences. St. Armands Circle and downtown Sarasota’s cultural attractions—shopping, galleries, theaters, and waterfront dining—are easily accessible, completing the appeal of this well-positioned coastal residence.

LONGBOAT KEY

3598 FAIR OAKS LANE

4 Beds

4 Baths

3,417 Sq.Ft.

$2,895,000

MLS#: A4677923

#A4674925

LONGBOAT KEY

640 LYONS LANE

3 Beds

3 Baths

2,130 Sq.Ft.

$2,845,000

MLS#: A4674925

Step inside this spacious residence to discover a clean, modern interior with a sophisticated Palm Beach vibe. Designed for both style and comfort, this home features a gracious great room featuring floor-to-ceiling windows that flood the interiors with natural light and open to the large, 765 square foot private terrace with a built-in gas grill—perfect for gardening, entertaining friends and family, or relaxing outdoors. The chef’s kitchen is outfitted with Poggenpohl cabinetry, Wolf appliances, a Sub-Zero refrigerator, and Sub-Zero wine and beverage refrigerator, blending elegance with functionality. The owner’s suite also boasts floor-to-ceiling windows, a custom designed closet, and a luxurious bathroom with a frameless walk-in shower, Toto mechanized commode, and double vanities. With generous square footage and a thoughtful layout, this residence easily accommodates overnight guests while maintaining a sense of privacy. Additional features include electronic blinds throughout, adding both convenience and sophistication. Designer light fixtures add an elegant touch throughout the home.
St. Regis Longboat Key offers 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 Gulf side living.

LONGBOAT KEY

1591 GULF OF MEXICO DRIVE 216

1 Beds

2 Baths

1,556 Sq.Ft.

$2,800,000

MLS#: A4665247

This is West Coast of Florida living at its finest, designed for those seeking a refined and effortless second home near the Gulf. Elevated and elegantly appointed, this custom residence is ideally located west of Gulf of Mexico Drive in the highly desirable Conrad Beach community on Longboat Key, where coastal serenity meets thoughtful design.

Surrounded by lush tropical landscaping with accent lighting, the home blends timeless island architecture with modern comforts ideal for seasonal or extended stays. Inside, an open and inviting floor plan centers around a gourmet kitchen featuring a large quartz island perfect for entertaining, abundant workspace, and seamless flow into the main living areas. A full in-house generator provides peace of mind while you are away, making ownership as easy as it is enjoyable.

Multiple porches and terraces, including a rooftop observation deck, create exceptional indoor-outdoor living and invite you to savor Gulf breezes and unforgettable West Coast Florida sunsets. The primary suite, located on the main living level, offers a private retreat with a spa-inspired bath and a serene balcony overlooking the tropical surroundings. Upstairs, guest bedrooms and a spacious loft-style family room provide flexible accommodations for visiting friends and family, all with access to wraparound terraces that capture the beauty of the island setting. The home comfortably sleeps ten, making it ideal for hosting while still maintaining privacy and comfort.

Outdoor living is equally well designed, with expansive decks perfect for quiet mornings or relaxed gatherings. A beautifully landscaped path leads to the oversized resort-style community pool, complete with bath facilities and entertaining space, offering all the benefits of a luxury amenity without the responsibility of maintaining a private pool. From the community observation deck, enjoy glimpses of the Gulf and dramatic evening skies.

Additional features include a two-car garage with storage and workshop space, an outdoor shower, high-impact windows and doors, and a screened ground-level lanai. The award-winning Conrad Beach community enhances the lock-and-leave lifestyle with lawn care, irrigation, and landscaping services included.

Just moments from pristine beaches, the charm of Longboat Key’s north end, marinas, and the dining and boutiques of St. Armands Circle, this home offers the ideal blend of privacy, convenience, and coastal living. Schedule your private showing and experience how effortless owning a second home on Florida’s West Coast can be.

LONGBOAT KEY

311 FIREHOUSE COURT

3 Beds

3 Baths

2,352 Sq.Ft.

$2,799,000

MLS#: A4665445

Experience the best of Longboat Key living in this elevated coastal retreat, ideally located in the desirable Conrad Beach community just a block from the Gulf of Mexico. Designed with timeless style and modern comfort in mind, this 4-bedroom, 4.5-bath residence offers sophisticated finishes, smart upgrades, and all the pleasures of island life without the upkeep of a private pool. Spanning 2,900 square feet, the open-concept layout showcases a chef’s kitchen with an oversized quartz island, premium appliances, and generous counter space ideal for entertaining family and friends. Light-filled second-level living and dining spaces open to an expansive porch and outdoor dining space , creating a seamless indoor-outdoor flow. The first living level features a serene primary suite with a spa-inspired bath and private balcony, offering a peaceful retreat. Upstairs guest suites provide privacy and comfort, with terraces to capture the island’s cooling breezes and glowing Gulf sunsets. A stunning rooftop deck with jacuzzi crowns the home, creating an unforgettable setting for evening relaxation or gatherings under the stars. Additional highlights include impact-rated windows and doors, elevator ready, and a two-car garage with ample storage. The award-winning Conrad Beach community offers a recently renovated resort-style pool with bath facilities and beautifully maintained landscaping, all just a short stroll from the shoreline. Enjoy the vibrant charm of nearby Anna Maria Island, Longbeach Village dining, marinas, and boutique shopping at St. Armands Circle and Sarasota. This home blends coastal sophistication, privacy, and comfort—an ideal winter haven to share with family and friends.

LONGBOAT KEY

333 FIREHOUSE COURT

4 Beds

4 Baths

2,900 Sq.Ft.

$2,795,000

MLS#: A4672573

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