One of the most popular communities provided by {{page_data.agentName}}

Long Boat Key

One of the most popular communities provided by The Graf Group of Coldwell Banker

Long Boat Key

About Long Boat Key

Longboat Key, Florida, is a tranquil paradise that offers the perfect blend of luxurious living and natural beauty. Nestled between the sparkling waters of the Gulf of Mexico and Sarasota Bay, residents enjoy stunning beaches, picturesque sunsets, and a laid-back, island lifestyle. The community is renowned for its upscale amenities, including gourmet dining, boutique shopping, and world-class golf courses, all while maintaining a quaint, small-town charm. With year-round warm weather, ample outdoor recreational activities, and a strong sense of community, Longboat Key is an ideal place for both relaxation and adventure, making it a highly desirable destination for those seeking a serene coastal retreat.
One of the most popular communities provided by The Graf Group of Coldwell Banker
455
# of Listings
2
Avg # of Bedrooms
$1,133
Avg. $ / Sq.Ft.
$2,061,288
Med. List Price

Browse Long Boat Key Real Estate Listings

455 Properties Found. Page 1 of 31.

**Pirce Improvement ~ Motivated Seller** Step into the island lifestyle you’ve always imagined at Privateer North, located behind the gates of the Longboat Key Club. This CORNER residence with over 1,400 sq. ft. invites you to wake each morning to the sound of waves and natural light streaming through wide glass doors. Sip your coffee on the balcony as Gulf breezes drift in, and in the evening, watch the sky transform with unforgettable Longboat Key sunsets.  Inside, thoughtful UPDATES create a fresh, welcoming home. The owners have recently installed a NEW ELECTRIC PANEL, added NEW LIGHTING, FRESH PAINT in areas where needed, and are offering the property FULLY TURN-KEY FURNISHED — so you can start enjoying it from day one. The OPEN LIVING AND DINING area flows easily for entertaining, while the SPLIT-BEDROOM design ensures privacy. The spacious primary suite features a WALK-IN CLOSET and SPA-STYLE BATH, while the guest suite provides a comfortable retreat for family and friends.
Privateer North has just completed a STUNNING MODERNIZATION of its common areas and elevators, complementing its prime beachfront setting. Amenities include a BEACHFRONT POOL AND SPA, FITNESS CENTER, SAUNA, TENNIS and PICKLEBALL courts, CONCIERGE service, and DIRECT BEACH ACCESS — everything you need for a true resort lifestyle.  With the new St. Regis Resort just minutes away, and St. Armands Circle and downtown Sarasota within easy reach, this home blends relaxation and sophistication in one of the Gulf Coast’s most desirable locations. Whether a seasonal retreat or full-time residence, Unit 204 offers the perfect balance of LUXURY, LIFESTYLE, and ISLAND CHARM.  Call the listing agent today for a V.I.P. tour!
#A4662463

LONGBOAT KEY

1050 LONGBOAT CLUB ROAD 204

2 Beds

2 Baths

1,409 Sq.Ft.

$874,900

MLS#: A4662463

Price reduced
Welcome to your private, gated estate on Longboat Key, where coastal luxury meets effortless sophistication. Boasting over 730 feet of water frontage, this stunning property offers panoramic views of Whitney Bayou and Harris Canal and provides the ultimate waterfront lifestyle. 
With 9,243 square feet of air-conditioned living space and a total of 21,562 square feet on over an acre of pristine land, this estate is a masterpiece of design and craftsmanship. Designed in the timeless British West Indies style, this home showcases vaulted ceilings, extensive trim detailing, white oak floors throughout, and two fireplaces, creating an ambiance of elegance and warmth.
The expansive covered patios and porches invite you to embrace the serenity of waterfront living, while the heated pool and an impressive 13' x 13' hot tub serve as the ultimate retreats. A custom outdoor fire pit, two outdoor kitchens, and indoor and outdoor pool tables elevate the entertainment experience.
For boating enthusiasts, this estate is unrivaled, featuring four low-profile boat lifts—the largest accommodating vessels up to 30,000 pounds, the second suitable for a vessel up to 20,000 pounds, and the third and fourth lifts each with a 5,000-pound capacity, ideal for jet skis, kayaks, and paddle boards. Located just 10 minutes from the Gulf of Mexico by boat and 5 minutes to Shore and Mar Vista restaurants, this is the perfect haven for life on the water.
Inside, the Wolf Sub-Zero appliances provide top-tier performance in a gourmet kitchen built for culinary excellence. A Control4 smart home system offers seamless automation throughout, while HVAC-equipped garages ensure comfort year-round. The multiple garages can accommodate up to 9 cars, and the massive driveway can host 20+ vehicles.
The residence boasts six spacious bedrooms, each with an en-suite bathroom, plus an additional full bath and two half baths. Designed for both productivity and leisure, the home features his and hers offices, a media/theater room, a fully equipped gym, sauna, golf simulator, tackle garage, and a workshop.
A private guest suite with a separate entrance includes a kitchenette, dining room, living room, bedroom, and bathroom, offering a luxurious retreat for visitors. With two state-of-the-art elevators, expansive landscaping, and a maintenance-free turf yard, this estate blends modern convenience with natural beauty.
Ideally located near pristine beaches, world-class shopping, and gourmet dining, this estate is the epitome of waterfront elegance and exclusivity. Experience the pinnacle of coastal living—this is truly paradise found.
#A4643123

LONGBOAT KEY

612 JUAN ANASCO DRIVE

6 Beds

7 Baths

9,243 Sq.Ft.

$22,750,000

MLS#: A4643123

Named the House of Columns by world-renowned, award-winning architect Carl Abbott, this palatial Bayfront estate stands as a singular expression of architectural distinction and craftsmanship. Encompassing close to five acres on the north end of Longboat Key spanning Sarasota Bay, the combined offering of 6610 and 6630 Gulf of Mexico Drive represents one of the most significant residential holdings available in the area, a legacy estate where endless views of sea and sky create an unforgettable backdrop for living. The property unfolds like a private peninsula, offering exceptional width, depth and privacy. On the eastern shoreline, calm bay waters reflect the morning light with open water, protected shoreline and bridgeless access to the Gulf of Mexico. The primary residence is gracefully positioned on the bayfront, designed to capture eastern exposure and long, tranquil water views across Sarasota Bay. Clean architectural lines, soaring interior volumes, and walls of glass create a continuous dialogue between interior and exterior. Ceilings soar up to 21 feet, allowing light to move freely throughout the home while maintaining warmth and livability. The elevator provides access across levels, while Lutron lighting and automated shades on every window and door allow the home to respond intuitively to the changing light of day. The residence has been impeccably maintained by its original owner, reflecting a level of care and stewardship rarely found. Infrastructure has been thoughtfully addressed, including a whole-home generator that ensures continuity and peace of mind. The owner’s garage sits under a cantilever with access to the interior elevator and an additional air-conditioned four-car garage with large workspace offers a total space for 6 cars and exceptional flexibility for collectors, hobbies or future customization. A lagoon-style pool sits within the landscape, offering a resort-like atmosphere while preserving privacy and water views. A private dock with two boat lifts provides immediate access to Sarasota Bay and the Intracoastal Waterway, creating a seamless boating lifestyle that complements the estate’s waterfrontage. The inclusion of 6630 Gulf of Mexico Drive allows owners to construct a guest house or secondary structure, offering flexibility for multigenerational living, guests, or staff accommodations, offering extraordinary future optionality and ensures the next owner retains control over one of Longboat Key’s irreplaceable resources, land. What ultimately distinguishes this offering is its irreplaceability. Estates of this size, with this combination of architectural pedigree, boating infrastructure, development flexibility and maintained condition are no longer being created. Despite its scale and seclusion, you are moments from the refined lifestyle Longboat Key is known for, private clubs, championship golf, fine dining, IMG Academy and the cultural offerings of Anna Maria Island, St. Armands Circle and downtown Sarasota just beyond the bridge. This is not merely a waterfront home, it is a generational legacy, unmatched in design, scale, privacy and location.
#A4681242

LONGBOAT KEY

6610 GULF OF MEXICO DRIVE

4 Beds

4 Baths

6,891 Sq.Ft.

$22,000,000

MLS#: A4681242

Price reduced
Regent’s Court: The Pinnacle of Luxury on Florida’s West Coast
Regents Court: Where Legend Meets Luxury

Beyond the gates of the Longboat Key Club lies an estate that doesn’t just live — it performs. A dramatic masterpiece perched on Florida’s west coast, this estate commands over an acre of pure beachfront with 150 feet of unspoiled Gulf frontage, where sky and water fuse in ever-changing hues at dawn and dusk.
Your arrival is nothing short of cinematic: majestic wrought-iron gates part to reveal a sweeping driveway paved in artistic stone, each curve leading closer to the heart of the home. A side-entry garage, cavernous in its capacity, hides generous storage; beside it, a full-house generator promises unbroken comfort even when the world goes dark.
Inside, every surface and silhouette feels sculpted for impact. Cream marble floors echo with light. Designer lighting drapes each room in mood and elegance. Premium stainless steel appliances anchor a gourmet kitchen, with a bar area that’s built for both intimate soirées and lavish celebrations. Across stately arches, French doors open into an office and dining space. 
Ascend via elevator through all four levels, each floor unveiling rooms with cathedral ceilings, balconies with sweeping views over the Gulf. The two-story library has custom woodwork. Adjacent to the large primary bedroom is the super-master bath with both tub and shower framing the Gulf in panoramic glory.
On the second living level are three guest suites with private porches that render a daily spectacle — mornings bathed in soft dawn light over the sand dunes and the Gulf, evenings lit by fading sun dancing across the waves. French doors open wide, blurring the boundary between indoors and the beach. 
The third living level includes an all inclusive guest quarters—your private sky-retreat. Two bedrooms, two baths, a full kitchen, a spacious living and TV room.  From its large, sweeping porch, the views stretch across Sarasota Bay and the Gulf’s glassy expanse. By day the Bay shimmers under sunlight, by dusk the city lights begin their soft glow. This is a space where family, friends—or guests—can escape, entertain, or simply soak in nature’s most breathtaking performances.
Outside is not secondary, but rather the heart of this sanctuary. Lush tropical landscaping surrounds the estate.  There is a NCAA lap pool with motorized cover, a deck edged with gas torches, fire pits that flicker under the stars. There’s an outdoor ice tub plus an outdoor kitchen with refrigerator and a gas grill. A special gym on the second floor is cooled to perfection, central control at your fingertips. Roll-safe shutters provide safety without sacrificing style.
At every moment, this home evokes a rare elegance — you’re not just observing the sunset over the Gulf, you are enveloped by it. Minutes from Sarasota, St. Armand’s Circle, Anna Maria — yet here, time moves differently, more luxuriously.
This is not just a home. This is a legacy.
#A4665431

LONGBOAT KEY

865 LONGBOAT CLUB ROAD

6 Beds

6 Baths

9,328 Sq.Ft.

$19,700,000

MLS#: A4665431

Where the sky opens wide above the Gulf and the shoreline runs uninterrupted, this extraordinary 12,000+ sq. ft. estate stands with a presence that defies comparison. Set on nearly 200 feet of pristine beachfront, the residence is elevated on pilings and wrapped in walls of glass that pull the Gulf’s horizon into every major living space. Inside, soaring cedar ceilings, exposed trusses, and dramatic lines create a sense of volume and warmth that is both refined and inviting. The great room unfolds beneath grand architectural beams and transitions effortlessly to expansive terraces above the sand. A richly crafted lounge with custom bar and billiards area brings a club-like sophistication to the home’s entertainment spaces. The extraordinary chef’s kitchen commands attention with custom inlaid cabinetry, dual oversized islands, professional-grade appliances, and a hidden pantry—ideal for both catered events and everyday living. The second-floor primary suite serves as a private escape with Gulf views, generous sitting area, and a spa-inspired bath. Additional bedroom suites offer privacy for guests, while flexible spaces—including offices, fitness room with sauna, and bonus areas—accommodate a variety of lifestyles. An elevated pool and spa overlook the beach, complemented by multiple decks and outdoor living areas that capture sunrise, sunset, and the sound of the surf. With two elevators, multi-car garage, and exceptional craftsmanship throughout, this is a residence designed for those who seek scale, presence, and true Gulf-front living.
#A4671535

LONGBOAT KEY

6685 GULF OF MEXICO DRIVE

8 Beds

8 Baths

12,752 Sq.Ft.

$15,550,000

MLS#: A4671535

Under Construction. You're in for something special with this new beachfront construction set to be completed by May, 2026. Located on over a quarter acre on Longboat Key, this contemporary luxury home is directly on the beach with stunning Gulf views. Designed with a modern coastal aesthetic, it’s built for both style and comfort. Inside no detail is overlooked. From sleek Walker Zanger porcelain tile to custom cabinetry and polished nickel fixtures, the finishes are top-tier. The gourmet kitchen features an expansive layout with a large waterfall-edge island, double Wolf ovens, Sub-Zero refrigeration, a full-size wine cooler, and a Wolf induction cooktop—everything you need for serious cooking or entertaining. Primary suite is a true showstopper with floor-to-ceiling glass sliders that open wide to a sweeping terrace. Gulf breezes flow through the space, and the shimmering azure water is always in view. Inside, the suite offers a spacious walk-in closet and a spa-like bath featuring tiled walls, a walk-in shower with multiple heads, a soaking tub, dual floating vanities, and a private water closet. Upstairs, an executive office and three generous bedroom suites—each with its own walk-in closet—gives plenty of space for family or guests. A fourth bedroom shares a cozy den, perfect for lounging or movie nights. The grand-level outdoor space takes full advantage of its beachfront setting with a 36-foot lap pool, sun shelf, heated spa, and a fully equipped summer kitchen with a grilling station—ideal for effortless entertaining, all just steps from the sand.
#A4648957

LONGBOAT KEY

6603 GULFSIDE ROAD

5 Beds

5 Baths

4,925 Sq.Ft.

$15,000,000

MLS#: A4648957

This Seaward Homes Curated Collection residence at 6489 Gulfside is ready for occupancy. Enjoy the ultimate Longboat Key lifestyle with your own direct Gulf-front private access and stunning views of the Gulf of Mexico. Designed by DSDG Architects, this home epitomizes exceptional quality and attention to detail.
Situated on a coveted 90' Gulf/Beach-front lot, the property offers soft sands, endless Gulf views, and miles of walkability.  
In 2025, Longboat Key completed a significant beach re-nourishment project, giving Gulfside Road homeowners one of the widest and deepest stretches of beach on the entire island. Equally notable, Gulfside Road is one of the rare Gulf-side streets set back from the main highway, offering a tranquil, private environment that feels worlds away from the activity of Gulf of Mexico Drive.
The main house, elevated over 15 feet, features 11' ceilings, four oversized en-suite bedrooms, and more than 6,600 sq ft of air-conditioned living space, including a grade-level, air-conditioned multipurpose room that can be tailored for wellness, fitness, or a variety of additional lifestyle needs.
The wide-open floor plan, generous room sizes, and large impact-rated safety glass sliding doors and windows fill the home with natural light. Two nearly 40' terraces on the main and second floors provide ideal spaces to enjoy the outdoor island lifestyle and breathtaking Gulf views.
Interior finishes by Studio G Homes elevate luxury living to the next level. The interior finishes include large-format porcelain tile and hardwood flooring, Italian-imported cabinetry, a custom floating steel-and-wood staircase, a three-stop elevator, 8' solid interior doors, high-efficiency mechanical systems, a top-of-the-line Thermador™ appliance package, AXOR™ and Hansgrohe™ plumbing fixtures, temperature-controlled wine storage, and detailed AV, lighting control, and security systems.
Exterior features include solid concrete and masonry construction on all floors, a deep concrete piling foundation for added strength, Longboard™ premium aluminum architectural details, and a fine light-sand exterior stucco finish. The resort-like pool area and custom spa are surrounded by a lush tropical landscape package. The garage accommodates four cars, with the option to add car lifts.
Longboat Key, an 11-mile barrier island, is just minutes from St. Armands Circle and downtown Sarasota. The Sarasota Bradenton International Airport is approximately 25 minutes away. Embrace the opportunity to own this unparalleled residence and experience the pinnacle of coastal luxury living.
#A4677413

LONGBOAT KEY

6489 GULFSIDE ROAD

4 Beds

4 Baths

6,616 Sq.Ft.

$14,995,000

MLS#: A4677413

Welcome to a once-in-a-generation private waterfront family compound on the coveted north end of Longboat Key—an extraordinary two-acre, fully gated coastal estate that blends architectural mastery, resort-level amenities, and rare development potential. Encompassing four buildable parcels (500, 510, 520 Nomas Way and 6680 Gulf of Mexico Drive), this legacy property offers unparalleled privacy, flexibility, and long-term value. From the moment you arrive, illuminated by classic Bevelo gas lanterns, the estate unfolds with intention and elegance. The custom-designed main residence is complemented by a separate 3-bedroom, 2-bath, 1,850-sq-ft guest home with a detached garage—perfect for extended family, guests, or staff accommodations. Every detail reflects thoughtful craftsmanship, from the 900-bottle red cedar wine cellar to the oversized custom wood-burning fireplace with gas option. Designed for both grand entertaining and everyday indulgence, the chef’s kitchen features natural gas cooking with Wolf and Sub-Zero appliances, while state-of-the-art home automation and whole-home sound elevate daily living. Step outside to a true private resort: a 15,000-gallon free-form pool with a 1,000-gallon spa, heating and chilling via reverse heat pump and natural gas, and an expansive custom tiki pavilion built for unforgettable gatherings. For boating enthusiasts, this estate is unmatched—165 feet of frontage on Bishops Bayou, two docks, three boat lifts, and deep-water, direct Intracoastal access. Across Gulf of Mexico Drive, deeded private beach access makes turquoise waters and nightly sunsets a daily ritual. Car collectors and hobbyists will appreciate six garages, including an automotive lift, plus a 50’ x 24’ covered pole barn for additional storage. Peace of mind is absolute with a 24-camera security system, safe room, elevator, and a 60kW natural gas generator powering the entire estate during any weather event. Fully fenced and gated, this property offers complete privacy without compromise. This is more than a home—it is a coastal masterpiece, a designer’s dream that exudes sophistication, balance, and harmony. An irreplaceable opportunity to own one of Longboat Key’s most remarkable waterfront estates, where luxury, security, and lifestyle converge in perfect alignment.
#A4682193

LONGBOAT KEY

6680 GULF OF MEXICO DRIVE

6 Beds

6 Baths

6,408 Sq.Ft.

$13,900,000

MLS#: A4682193

This bespoke crafted casually elegant furnished residence is in the exclusive gated Lighthouse Point waterfront enclave of just 16 custom residences at the southern tip of Longboat Key. Lighthouse Point is a peninsula nestled on a deep-water boat basin at the edge of the Intracoastal Waterway and New Pass. This residence has been completely remodeled within the past couple years, taken down to the studs to create the ideal coastal waterfront estate. The improvements included new impact glass windows and doors throughout and a new tile roof. The furnishings are chosen to make the space comfortable for both relaxing seaside living, as well as hosting family and guests. No detail has been overlooked. The first level includes an open floor plan with a living, family and dining room with a separate media room, and the fifth bedroom with double bunk beds for the little ones. Entering this stunning home, you are welcomed into a grand space, and beyond the beautiful kitchen with island seating, that includes the La Cornue French gas range as the focal point. The living and family rooms each have a gas fireplace. The main floor rooms overlook an expansive terrace and large heated pool with sun shelf chaises, back yard with plenty of space for games, private beach, and the Gulf of Mexico. Take the stately staircase or elevator to the second floor where the primary bedroom and three en-suite guest bedrooms are. The primary and two of the guest suites connect to a wide terrace overlooking the Gulf and Longboat Pass. Enjoy the Gulf’s vibrant sunset skies from the primary suite with spacious bedroom living space, meticulously appointed spa-like bath area, three walk-in closets and gas fireplace. There is a three-car side entry garage with room for storage. Down the street at the community dock is a new 16,000lb boat lift. Owners in the Lighthouse Point neighborhood enjoy their own tennis court plus the nearby gulf front beach, easy access to the Resort at the Longboat Key Club and the Links Golf Course and fitness center with famed St. Armand’s Circle shopping and dining district just over a mile away. Sarasota and its famed arts and entertainment is just 5 miles away. .
#A4681304

LONGBOAT KEY

70 LIGHTHOUSE POINT DRIVE

5 Beds

5 Baths

5,475 Sq.Ft.

$13,750,000

MLS#: A4681304

Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living. Ideal for multi-generational gatherings, the clubroom serves as a fantastic bonus space, featuring a wet bar equipped with an ice maker, bar sink, and wine fridge. The gourmet kitchen is a chef’s dream, showcasing top-of-the-line Wolf and Sub-Zero appliances, including a 6-burner gas cooktop, double ovens, and an integrated cabinet front side-by-side refrigerator/freezer. A semi-private elevator with keyless entry transports you directly from your private two-car garage to your residence. The owner’s suite offers a spacious walk-in closet, a luxurious soaking tub, a frameless walk-in shower, and dual vanities with separate water closets. Designed with technology-ready infrastructure, this home allows for easy customization of your automation preferences. Located within the first branded residential community and ultra-luxe 5-star resort hotel on the Gulf, The Residences at The St. Regis Longboat Key blend legendary service with the allure of a serene seaside retreat. Spanning over 17 acres with 800 feet of direct beachfront, residents can indulge in unparalleled amenities, including signature St. Regis Butler and Concierge services, a world-renowned spa, in-residence dining, a resident-only pool and spa, a private clubhouse, a fitness center, and beachside cabanas. Discover a life of luxury and leisure at The Residences at The St. Regis Longboat Key—where every day feels like a getaway. The owner will consider a lease purchase with acceptable terms on this residence.
#A4627926

LONGBOAT KEY

1561 GULF OF MEXICO DRIVE 403

3 Beds

3 Baths

4,187 Sq.Ft.

$13,000,000

MLS#: A4627926

Price reduced
A Gulf-Front Masterpiece on Longboat Key! This stunning Gulf-front estate is perfectly placed on nearly an acre of pristine Gulf-front property along the shoreline on Longboat Key. With direct Gulf frontage, this architectural masterpiece offers more than 6,900 square feet of refined interiors and panoramic views that stretch endlessly across the Gulf of Mexico. Designed for both privacy and grand-scale entertaining, the residence balances timeless craftsmanship with recent enhancements including a 2025 primary bath remodel, newer French doors, and resort-style pool and spa with natural gas heating and fire pit.
From the moment you arrive through the circular drive, the home’s elegant façade, manicured landscaping, and elevated design make a commanding first impression. Inside, expansive living areas are defined by travertine and hardwood flooring, soaring coffered ceilings, crown molding, and walls of glass framing breathtaking views. The open floor plan flows effortlessly from the formal living and dining rooms to the family room and gourmet kitchen, designed for effortless entertaining.
The chef’s kitchen showcases custom wood cabinetry, granite counters, a large island, high-end appliances, double ovens, and a breakfast nook overlooking the Gulf. The main-floor primary suite offers a serene retreat with direct beach views, its own private terrace, dual walk-in closets, and a spa-like new bath featuring dual vanities, stone counters, and a freestanding soaking tub. A private elevator connects all levels, including a versatile second-story loft, media room, and four additional bedrooms (some en-suite) providing ample comfort for family and guests.
The outdoor living space defines Florida luxury—complete with an expansive travertine deck, heated pool and spa, summer kitchen, and multiple covered terraces designed for dining and relaxation. Enjoy vibrant sunsets over the Gulf from nearly every vantage point. The property also features new hurricane-rated French doors, a whole-house generator with raised platform, and a three-car side-entry garage with guest parking.
Located on the prestigious north end of Longboat Key, this gated estate offers the perfect balance of seclusion and accessibility. Stroll along miles of private beach or take a short drive to the Longboat Key Club, offering championship golf, tennis, and fine dining. Just minutes away, St. Armands Circle and downtown Sarasota offer a vibrant mix of boutique shopping, art galleries, and acclaimed restaurants. With world-class marinas, cultural landmarks, and pristine beaches within reach, this exceptional residence captures the very best of Sarasota’s luxury coastal lifestyle.
Offering an unparalleled combination of design, craftsmanship, and Gulf-front serenity, 6001 Gulf of Mexico Drive stands as a statement of timeless coastal elegance—where every sunset feels like home.
#A4667111

LONGBOAT KEY

6001 GULF OF MEXICO DRIVE

5 Beds

5 Baths

6,959 Sq.Ft.

$10,995,000

MLS#: A4667111

Rare opportunity, two fully furnished TWIN residences (TWO UNITS BEING SOLD AS ONE 4473+4477 Gulf of Mexico Drive ). Directly on the pristine shores of Longboat Key! Combined 8 bedrooms, 8 Bathrooms. Spanning nearly 6,000 sq. ft., on .58 GULF-FRONT acres, this two-story property offers mirror-image residences, each thoughtfully decorated with both modern and timeless designs.  A true investment gem—live in one, rent the other, enjoy a multi-generational retreat, or explore redevelopment potential on this premier beachfront site.  Direct Gulf-front access — step onto the sand from your back door.  Sweeping water views from nearly every room!  State-of-the-art kitchens with high-end appliances, including Wolf gas range, Sub-Zero refrigerator, and Miele dishwasher.  Open-concept living & dining with fireplaces. Engineered hardwood floors, impact-rated windows/doors & storm shutters. Main-level guest suites + upstairs Gulf-front primary suites with spa-style marble baths & dual walk-in closets. Outdoor highlights include: twin Gulf-front pools, pavered decks and walkways, and two two-car garages.  This sought-after location is minutes to Longboat Key Club, St. Armands Circle and Downtown Sarasota (golf, tennis, dining, shopping). Endless Options: Luxury primary home, beachfront getaway, income-producing property, or redevelopment opportunity—this rare duplex delivers the ultimate in coastal living and investment versatility.
#A4666527

LONGBOAT KEY

4473 GULF OF MEXICO DRIVE 4473

8 Beds

8 Baths

5,886 Sq.Ft.

$10,900,000

MLS#: A4666527

100' of direct beach and gulf frontage..... Welcome to Paradise! Experience the ultimate in Longboat Key and Gulf-front luxury with this spectacular nearly 6,000 sq. ft. beachfront estate on Longboat Key. Perfectly positioned on a pristine stretch of white-sand shoreline, this gorgeous beach home offers unobstructed, panoramic views of the Gulf of Mexico from nearly every room in the home. Also featuring over 3,000 sq. ft of under-roof outdoor relaxation and entertainment space. Designed for family gatherings and beach front fun, this is the perfect beach home for tranquil coastal living. This beach home features 6 bedrooms, 6.5 bathrooms, a den and a family room, as well as a stunning 24' x 24' rooftop sun deck. Built in 2002, this waterfront beauty offers many unique details like the Mahogany front door, elevator to all 3 levels, all new exterior paint and interior paint, and best of all three expansive levels of outdoor living space, each capturing the beauty of daily sunsets and unobstructed Gulf and beach views. At the heart of your beachfront oasis is a newly refurbished resort-style pool and new paver patio, framed by swaying palms and endless water views. Just steps beyond the pool is access to your 100' of private beach frontage leading directly to the soft sand and crystal-blue Gulf waters. The main level Owner's suite is large, with direct and unobstructed Gulf and beach views.  The kitchen is spacious and open, with top-of-the-line appliances and direct Gulf and beach views to enjoy while you cook. The guest bedroom suites are all spacious, with ensuite bathrooms and great Gulf and beach views from every bedroom. Whether you’re seeking a serene retreat or an entertainer's dream, this exceptional Longboat Key residence delivers unparalleled beauty, privacy, and a front-row seat to Florida’s most breathtaking coastline. Hurry up and get here, the views are spectacular!
#A4666887

LONGBOAT KEY

6477 GULFSIDE ROAD

6 Beds

6 Baths

5,862 Sq.Ft.

$10,000,000

MLS#: A4666887

Exquisite Palladian-Style Waterfront Estate Located on the serene shores of Sarasota Bay, this home epitomizes elegance and sophistication. Designed by Cliff Scholz and meticulously crafted by Murray Homes, this, 5,300-square-foot masterpiece is situated in a double-gated community offering unparalleled privacy and exclusivity. Perched at the end of a quiet cul-de-sac, the property boasts almost 200 feet of pristine waterfront, with breathtaking views of the downtown Sarasota skyline and a protected deep-water yacht slip. Deeded access to a private Gulf of Mexico beach club enhances the ultimate coastal lifestyle. Inside, the home features an exceptional floor plan with four luxurious bedroom suites and numerous entertainment spaces, including a formal living room, dining room, family room, and a gourmet kitchen equipped for the finest culinary creations. Expansive waterfront terraces, a redesigned viewing porch, and his-and-her offices add to the home's functional elegance. Every detail has been executed to perfection, from the impeccable millwork to the finest finishes throughout. With magical views from every room, this estate embodies class, comfort, and privacy in one of Sarasota's most coveted locations. Experience refined waterfront living at its finest.
#A4671218

LONGBOAT KEY

560 HARBOR POINT ROAD

4 Beds

5 Baths

5,245 Sq.Ft.

$9,700,000

MLS#: A4671218

Price reduced
Gulf front Masterpiece with Bayside Boathouse and 12klb lift 
 
Experience the pinnacle of coastal living at this unparalleled Gulf-to-Bay estate on Longboat Key, where 100 feet of private, sugar-white beachfront meets the rare luxury of a deeded bayside boathouse—a coveted feature seldom available on the island. For the discerning boater, this exceptional amenity includes a 12,000-lb lift and upgraded dockage on tranquil Sarasota Bay, allowing seamless access to open water adventures while preserving the serenity of Gulf-front living.
 
Architecturally envisioned by Clifford M. Scholz and brought to life by Perrone Construction, the residence is a timeless fusion of coastal elegance and enduring craftsmanship. Elevated concrete block construction, a newly installed metal roof, and impact-rated windows ensure peace of mind, while expansive verandas and elevated terraces provide panoramic views of the Gulf, Bay, and captivating sunsets.
 
Spanning three levels, the home’s interior is equally refined 4BR/4,224sf (7,758sf total) - anchored by a gourmet kitchen with Sub-Zero, Viking, and Neff appointments, and graced with fluid indoor-outdoor spaces designed for both grand-scale entertaining and quiet personal retreats. The primary suite is a sanctuary unto itself, featuring dual walk-in closets, spa-inspired bath, and breathtaking views of the Gulf from its private balcony.
The ground level offers over 2,600 sq ft of flex space, ideal for a collector’s garage, home gym, or additional guest accommodations. Outdoors, the Gulf-front pool deck with summer kitchen invites year-round al fresco living, while a private path leads directly to one of Florida’s most pristine beaches.
 
Perfectly positioned on North Longboat Key - near Anna Maria Island, St. Armands Circle, and downtown Sarasota, this rare estate offers absolute privacy without sacrificing access to the region’s finest dining, shopping, and cultural experiences.
This is not simply a beachfront home—it is an irreplaceable legacy property offering the best of both Gulf-front tranquility and Bayfront boating. Private showings by appointment only for qualified buyers.
#A4665992

LONGBOAT KEY

6161 GULF OF MEXICO DRIVE

4 Beds

4 Baths

4,224 Sq.Ft.

$9,400,000

MLS#: A4665992

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