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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

$791

Avg. $ / Sq.Ft.

$1,307,085

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

417 Properties Found. Page 2 of 28.

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

$5,600,000

MLS#: A4632347

Rarely available Bay Isles Harbor bayfront lot. Enjoy incredible sweeping Sarasota Bay views in the prestigious Harbor section of Bay Isles. The property is at the end of a cul-de-sac on an oversized 16,000-square-foot lot with 150 feet of canal frontage overlooking Sarasota Bay. This is an incredible opportunity to build your dream residence on an extraordinary Bay Isles Harbor Lot with panoramic Sarasota Bay views. Owners enjoy the private Bay Isles lifestyle behind the gates, with access to the Bay Isles Beach Club and Longboat Key Club's Harbourside Golf Course, Tennis Gardens and other amenities available to club members. Architect renderings available.

LONGBOAT KEY

1630 HARBOR CAY LANE

None Beds

None Baths

0.37 acres

$5,595,000

MLS#: A4657747

#A4657152

LONGBOAT KEY

670 OLD COMPASS ROAD

5 Beds

5 Baths

5,792 Sq.Ft.

$5,495,000

MLS#: A4657152

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.

$5,425,000

MLS#: A4657691

#A4613404

LONGBOAT KEY

7147 LA LENAIRE DRIVE

5 Beds

5 Baths

8,170 Sq.Ft.

$5,250,000

MLS#: A4613404

#A4661312

LONGBOAT KEY

569 BAYVIEW DRIVE

4 Beds

4 Baths

5,282 Sq.Ft.

$5,199,950

MLS#: A4661312

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

DISCOVER THE DIFFERENCE—A TRUE LUXURY CONDO IN A BUYER’S MARKET

Why This Longboat Key Residence Stands Above the Rest:

This isn’t just another beachfront condo—this is a thoughtfully curated, luxury retreat where every detail has been considered, and every upgrade already completed. Enjoy peace of mind with all updates required by Florida’s new condo legislation already done and paid for—no surprise assessments here. From new roofs in 2024 to updated elevator systems, fire alarms, and lush new landscaping, this is one of the few buildings on Longboat Key where the heavy lifting is complete.

Unmatched Perks You’ll Rarely Find Elsewhere:

Full-time, on-site staff provide concierge-level service whether you're in residence or away.
No size restrictions on two dogs—finally, bring your big dogs to the beach.
Private two-car garage with additional storage—a true rarity for beachfront condos.
Grill on your terrace—yes, it’s allowed here.
A SHOWCASE OF COASTAL SOPHISTICATION
Step into over 3,000 sq ft of fully renovated, elegantly appointed interior living space—complete with 3 bedrooms and 3 baths, designed for both upscale entertaining and serene daily living. The crown jewel? A 1,000 sq ft wraparound balcony with a built-in outdoor kitchen, where panoramic Gulf views set the scene for unforgettable evenings.

Interior Highlights:

Expansive open-concept floorplan with high-end finishes throughout
Chef’s kitchen with Wolf appliances and a custom eat-in island
Luxury primary suite with separate his-and-hers en-suite baths, private toilet rooms, and dual vanities
Private guest wing with sitting room, terrace, and separate entrance—perfect for long-term guests
Floor-to-ceiling hurricane-impact glass for maximum light and storm security (no damage from recent hurricanes)
Gas appliances, including outdoor grill permitted on your terrace
EXCLUSIVE COMMUNITY AMENITIES:

Only 32 residences ensure a quiet, boutique feel
Pet-friendly: 2 dogs allowed with no size restrictions
Beachfront pool, sundeck, and direct beach access
Fitness center, sauna, and steam room
Clubhouse for resident events
Private fishing pier
24-hour security and on-site management
Full-time maintenance, landscaping, and housekeeping staff ensure the grounds are always immaculate
Walkable to grocery, pharmacy, golf, and tennis
And yes... 365 sunsets a year
A UNIQUE AND PRIVATE COASTAL RETREAT—READY NOW
This is a rare opportunity to own a move-in ready, beachfront condo in a well-managed building with no looming assessments or headaches. Every detail has been handled—just bring your flip-flops and start living the Longboat lifestyle.

Schedule your private tour today.

LONGBOAT KEY

2333 GULF OF MEXICO DR 1A2

3 Beds

2 Baths

4,179 Sq.Ft.

$4,950,000

MLS#: A4646994

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.

$4,599,000

MLS#: A4661988

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. 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

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

3,770 Sq.Ft.

$4,495,000

MLS#: A4636316

#A4655358

LONGBOAT KEY

590 DE NARVAEZ DRIVE

4 Beds

3 Baths

4,195 Sq.Ft.

$4,340,000

MLS#: A4655358

Experience Boutique Gulf-Front Luxury at Vizcaya on Longboat Key - Discover a rare opportunity to own in Vizcaya—Longboat Key’s premier low-density beachfront enclave, where just 31 residences share 9 lushly landscaped acres along one of the island’s quietest stretches of sand. Set well back from Gulf of Mexico Drive, you’ll hear waves instead of traffic, and with no public beach access nearby, your shoreline feels like a private retreat.
Unmatched Peace of Mind - Every major update required under Florida’s new condo legislation is already completed and fully funded—no surprise assessments. Recent upgrades include 2024 roofs, modernized elevators, enhanced fire systems, and refreshed landscaping. This is one of the few Gulf-front communities where the heavy lifting is done.
White-Glove Service - A full-time on-site staff—concierge, maintenance, landscaping, and housekeeping—delivers personalized service whether you’re in residence or away. With 24-hour security and a staffed guard gate, life here is effortless and secure.
A Residence Designed for Coastal Sophistication - Spanning over 3,000 sq ft with 3 bedrooms, 3 baths, and a den, this residence lives like a single-family home in the sky. Windows on all four sides fill the space with natural light and Gulf-to-Bay cross-breezes. The wraparound 1,000 sq ft terrace—with a built-in natural gas grill and panoramic, year-round sunset views—sets the stage for unforgettable evenings. This is one of the select Vizcaya residences where the sun can be seen sinking directly into the Gulf all 12 months of the year.
Rare Conveniences You Won’t Find Elsewhere
• Oversized private two-car garage with abundant storage
• Two large dogs welcome—no size limit
• Natural gas connection for outdoor and indoor appliances
• Flexible floorplans with only one plumbing stack—perfect for future remodeling
• Balcony grilling permitted (a rarity on the Key)
Resort-Caliber Amenities - Beachfront lap pool & sundeck • Direct beach access • Private fishing pier & groin • Fitness center, sauna & steam room • Resident clubhouse • Lush tropical grounds maintained to perfection
Close proximity to grocery, pharmacy, the LBK Tennis Center, and golf.
Vizcaya’s combination of exclusivity, service, and location simply doesn’t exist anywhere else on Longboat Key. With no pending assessments and every detail addressed, this residence is ready for your immediate enjoyment. Schedule your private showing today and experience the rare elegance, privacy, and service that make Vizcaya truly one of a kind.

LONGBOAT KEY

2333 GULF OF MEXICO DRIVE 1A3

3 Beds

2 Baths

4,179 Sq.Ft.

$4,250,000

MLS#: A4661324

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

6,095 Sq.Ft.

$4,250,000

MLS#: A4643565

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