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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

$828

Avg. $ / Sq.Ft.

$1,409,238

Med. List Price

Browse Long Boat Key Real Estate Listings

All listings

$250,000 - $500,000

417 Properties Found. Page 2 of 28.

Experience an unparalleled coastal retreat where the gulf meets impeccable design and technology. Beyond photographs or video, stepping into this home is an invitation to a lifestyle like no other. Boasting direct oceanfront views, crafted by Hughes Design Associates, this residence epitomizes sophistication through its refined neutral palette and innovative smart home integration. Each detail has been meticulously curated, from the luxurious electric drapes that reveal stunning vistas at the touch of a button to the expansive 1,800-square-foot astro-turfed rear patio, ideal for enjoying the sun-drenched ambiance. Every aspect of this residence is designed to elevate daily living. Bask in the Florida sunshine as the residence opens seamlessly to the outdoors, inviting private moments on the game-ready patio, and discover state-of-the-art amenities, including a whole-home water filtration system and a personal steam shower. This end-unit layout is flooded with natural light, enhancing the airy openness of the living spaces, four fully appointed bedroom suites, and a versatile den/office. Every feature speaks of luxury and precision from the Wolf-Sub-Zero appliance suite, quartz countertops and Italian cabinetry to the high-end TOTO electronic toilets with built-in bidets, Waterworks fixtures, frameless walk-in showers, impact-rated floor-to-ceiling windows and sliding doors. Enjoy an outdoor summer kitchen on the main balcony and the convenience of a private two-car garage. Sage on Longboat Key, designed by the renowned Hoyt Architects, is a boutique beachfront community where sophistication and exclusivity meet. With only 16 luxury residences, each home offers unobstructed gulf views and unmatched services, including 24-hour white-glove concierge and security, poolside and beach attendants, and exclusive amenities. The 260 feet of pristine gulf shoreline hosts an oceanfront heated Olympic lap pool, sundeck with chaise lounges, private cabanas, fire pit, and a fully equipped fitness center in a pet-friendly environment. Seize this rare opportunity to reside in Sage on Longboat Key, a sanctuary where luxury seamlessly intersects with cutting-edge technology and coastal elegance, making every day a celebration of refined beachfront living.

LONGBOAT KEY

4651 GULF OF MEXICO DRIVE 402

4 Beds

4 Baths

6,420 Sq.Ft.

$5,999,000

MLS#: A4627248

Embrace unparalleled modern elegance and coastal serenity at Infinity on Longboat Key, where refined architecture meets the timeless beauty of the Gulf of Mexico. This exclusive boutique condominium boasts only 11 meticulously designed residences, offering a private and luxurious retreat for those seeking a sophisticated island lifestyle. From your private elevator, enter a spacious foyer that flows into an expansive living area, where floor-to-ceiling glass sliders frame breathtaking Gulf views. Beyond, a large covered balcony with an outdoor kitchen and multiple seating areas beckons, perfect for alfresco dining amid endless ocean vistas. The open-concept kitchen exudes sophistication through its thoughtful design. Custom cabinetry in warm wood tones pairs beautifully with pristine stone countertops and Italian Britannium backsplash. Premium stainless steel appliances, including a gas cooktop and sleek hood, anchor the space. A central island provides both functionality and visual interest, while elegant pendant lighting and expansive Gulf views elevate the aesthetic, creating an inviting culinary environment that seamlessly blends style and practicality. The exquisite primary suite is a haven of calm, with sliders opening to a private balcony where you’ll awaken to the sound of waves and views of turquoise waters lapping sugar-white sands. The spa-inspired primary bath offers a tranquil escape, featuring dual vanities, a water closet, and a spacious walk-in shower. Thoughtfully designed guest suites ensure privacy and comfort. A versatile flex room provides endless possibilities, whether used as a home office, media room, or den. Additional conveniences include a well-equipped laundry room with ample counter space and storage. This condo comes with two private garages that can fit four cars. Resort-style amenities elevate the living experience with a beachfront heated pool, private spa overlooking the beach, large sun deck, beach access, an outdoor entertainment area, clubhouse with catering kitchen, fitness center, and pickleball/tennis courts. Infinity’s prime location on Longboat Key provides effortless access to St. Armands Circle’s world-class shopping and dining, as well as the vibrant cultural offerings of downtown Sarasota. Golf enthusiasts can enjoy nearby championship courses, while boating enthusiasts have easy access to marinas and coastal waterways.

LONGBOAT KEY

4765 GULF OF MEXICO DRIVE B202

3 Beds

3 Baths

4,808 Sq.Ft.

$5,995,000

MLS#: A4645607

New on site 3 days ago

#A4663499

LONGBOAT KEY

524 HALYARD LN

4 Beds

4 Baths

5,168 Sq.Ft.

$5,750,000

MLS#: A4663499

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

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