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$4,350,000
5 Beds ⋅ 6 Baths ⋅ 2026024474 MLS
Where timeless island architecture meets modern luxury, this exceptional Captiva retreat offers the rare combination of privacy, craftsmanship, and outstanding income-producing potential. Designed by acclaimed architect Bud Lawrence and situated on a premier corner lot just steps from both the Gulf beach and bay, this 5-bedroom, 5.5-bath residence was built for both relaxed island living and unforgettable entertaining. Surrounded by lush tropical landscaping, the home centers around an impressive two-story screened lanai featuring a PebbleTec heated pool and spa, waterfall, waterslide, expansive covered living areas, and a fully equipped outdoor kitchen with a built-in Thermador grilling station. Whether hosting family gatherings or accommodating large groups, the floor plan is designed to comfortably sleep multiple generations and guests with two private primary suites, three additional guest suites, and elevator access to all levels. Inside, custom craftsmanship is showcased throughout with Brazilian cherry wood flooring, marble finishes, handcrafted Sinker Cypress doors, custom cabinetry, imported roof tiles, decorative precast architectural details, and copper gutters and downspouts. The gourmet kitchen is complemented by dual wine coolers and generous entertaining space, while extensive technology upgrades include a Control4 smart home system, a 140-inch projection screen, surround sound, and integrated outdoor audio. Perfectly positioned in the heart of Captiva Island, owners and guests can easily walk to the beach, bay, restaurants, shops, marinas, and island attractions. With its desirable location, spacious layout, resort-style amenities, and ability to accommodate larger groups, the property also offers exceptional vacation rental potential in one of Southwest Florida's most sought-after island destinations. A rare opportunity to own a distinctive Captiva residence where luxury, location, and lifestyle come together.

15161 Wiles Drive, Captiva
$6,995,000
6 Beds ⋅ 5 Baths ⋅ 2026023434 MLS
At the southernmost tip of Captiva Island, where the turquoise waters of the Gulf meet the tranquil expanse of Pine Island Sound, lies one of Southwest Florida’s extraordinary residential offerings. Encompassing more than an acre stretching seamlessly from Gulf to Bay, this private estate commands an exceptionally rare setting immersed in water, light and natural beauty from every direction. Beyond the gated entrance, a dramatic composition of architecture and landscape unfolds. A resort-style pool and spa, lush tropical grounds, and a private dock with boat lift create a lifestyle defined by effortless access to the open Gulf and protected waters of the bay. Few properties can claim such a remarkable dual-waterfront existence. Designed to celebrate its surroundings, the residence is a masterful blend of warmth, craftsmanship and connection to nature. Stunning flooring, beamed ceilings, and thoughtfully curated finishes create an atmosphere that is sophisticated and inviting. Expansive walls of impact-rated glass frame panoramic vistas at every turn, transforming the ever-changing interplay of sea, sky and light into living works of art. The grand living room serves as the heart of the home, anchored by a striking fireplace and framed by breathtaking waterfront panoramas. To the west, endless views of sugar white beaches, the shimmering Gulf and Captiva’s legendary sunsets unfold. To the east, Pine Island Sound, mangrove islands and dramatic coastal skies create an equally captivating backdrop. The kitchen blends timeless charm with modern functionality, featuring exceptional millwork, premium appliances and a unique wood-burning fireplace that lends an unexpected touch of character. Flowing seamlessly to the bayfront lanai, it invites leisurely mornings overlooking the water and unforgettable evenings gathered around the firepit beneath the stars. The primary suite is a retreat unlike any other. A central fireplace separates intimate living spaces connected by rich wood flooring designed to embrace the estate’s dual-waterfront setting. One side opens to a private balcony overlooking the Gulf, while the other captures mesmerizing bay views through a tranquil window seat. The spa-inspired bath has been beautifully updated and offers the rare luxury of spectacular water views. Serviced by a private elevator connecting all levels, each guest suite enjoys its unique perspective of the surrounding coastal landscape. Outside, a private dock extends into the bay, providing immediate access to world-class boating, fishing and island exploration, while a private path leads directly to Captiva’s famed beaches. A rare offering, this estate represents the pinnacle of island living, a place where architecture and nature exist in harmony, and where every sunrise and sunset unfolds over water. Rarely does a property capture the essence of Captiva so completely.

17201 Captiva Drive, Captiva
$24,950,000
6 Beds ⋅ 7 Baths ⋅ 2026012050 MLS
Set on 4.55 acres at the very end of West Gulf Drive, known as Sanibel's prestigious Gold Coast, on a private cul-de-sac, this extraordinary beachfront estate offers 245 ft of direct Beach & Gulf frontage, exceptional privacy, and a caliber of craftsmanship rarely seen anywhere in SWFL. Built without compromise, and running parallel to the sunset, allowing the home to capture Sanibel’s legendary Gulf views & Sunsets. A rare legacy estate. Encompassing nearly 20,000 SF with 6 bedrooms, a private office, 6.5 baths, and white-sand beach & water views from every room. Grand in scale yet livable, conceived as a multigenerational coastal retreat, suited for intimate family life, extended guest stays, and entertaining. Professionally decorated & furnished, a reflection of craftsmanship. The great room is dramatic and refined, anchored by 3 custom Barlas Baylar chandeliers, a hand-carved Calacatta marble fireplace mantel, herringbone hickory floors, mahogany ceiling beams with integrated surround sound, and concealed air systems preserving clean architectural lines. A full-length illuminated bar with underlit crystal counters brings the ambiance of a private five-star lounge, while integrated Crestron & Lutron systems provide sophisticated control of lighting, media, comfort, and shade. A Chef’s kitchen & separate service kitchen are outfitted with Thermador Pro Appliances, custom cabinetry, designer hardware, and a full butler’s pantry, ideal for private chef service & entertaining. An elevator provides seamless access across levels, while a dumbwaiter offers discreet convenience for household needs. Custom hand-crafted doors highlight the home’s attention to detail. Built to exceptional standards, the residence features a copper roof w/ matching copper gutters, $1.4M in Hartman windows & doors, and full hurricane shutters for an exceptional level of coastal protection. The Primary Wing offers 2 Gulf-front suites and office. The primary suite features a fireplace, private balcony overlooking the Gulf, direct beach access, a morning kitchen, advanced security features, and an exceptional bath w/ indoor & outdoor showers, a steam shower, an extraordinary walk-in wardrobe, dedicated laundry, Toto toilets in every bathroom. Guest accommodations are designed to provide comfort & privacy, including a 3rd-level suite with breathtaking views of Sanibel’s celebrated sunsets. Beyond its principal living spaces, the home offers scale to have a private gym, spa, game room, and lifestyle spaces tailored to multigenerational living & extended guest stays. Outdoor living rivals a luxury resort, w/ a beachfront pool & spa, lap pool, outdoor kitchen, lounge pavilion with reclaimed wood & fireplace, and a beachside putting green. Additional lot separately available, offering the opportunity to expand or create a private compound. Framed by palms, Gulf breezes, and the sound of waves, this ultra-private residence is one of the most significant estates in Florida.

4405 W Gulf Drive, Sanibel
$8,995,000
5 Beds ⋅ 5 Baths ⋅ 2026006746 MLS
Majestic Gulf-front estate located on West Gulf Drive, Sanibel Island’s most coveted and prestigious beachfront address. Widely regarded as the premier location on the island, West Gulf Drive offers expansive estate-sized parcels, exceptional privacy, no HOA restrictions, and some of the quietest, least-traveled beaches on Sanibel. For those seeking the finest beachfront living, this is simply where you want to be. Set back from both the road and the shoreline, the property enjoys a rare sense of seclusion while maintaining breathtaking, unobstructed Gulf of Mexico views and spectacular sunsets. Elevated for peace of mind, the approach is framed by lush, tropical landscaping that immediately sets the tone, private, serene, and resort-like from the moment you arrive. The residence blends Sanibel’s relaxed coastal charm with the refined architectural presence often associated with Palm Beach and Naples, elegant yet approachable, luxurious without pretense. Designed to function as a true home rather than a showpiece alone, the interior is warm, inviting, and ideal for entertaining, extended family stays, and memorable gatherings. Upon entry, the volume of the main living area is immediately felt, highlighted by soaring beam ceilings, remarkable architectural detailing, and exquisite millwork throughout. The design strikes a perfect balance between formal and casual, grand in scale yet comfortable and livable, with a flow that feels both intentional and effortless. Mediterranean-inspired architecture gives the home a timeless character, complemented by expansive indoor and outdoor living spaces. Multiple lanais and deck areas invite effortless Gulf-front living, while the tranquil, resort-style pool area offers a peaceful retreat with sweeping water views and unforgettable sunsets. This meticulously built estate includes luxury amenities expected at this caliber, including an elevator, multiple game and recreation rooms, wine room, theater, office, indoor and outdoor kitchens, and flexible spaces for optional additional bedrooms. Professionally decorated with custom-designed furnishings, the residence is offered fully appointed, creating a rare turnkey opportunity. A true family compound and legacy property, this extraordinary West Gulf Drive estate offers unmatched privacy, prestige, and livability in one of Sanibel Island’s most iconic beachfront settings.

3767 W Gulf Drive, Sanibel
$4,749,000
6 Beds ⋅ 7 Baths ⋅ 2025024133 MLS
Experience the timeless coastal allure of 15160 Captiva Drive, a stunning estate designed with a rare reverse floor plan to capture sweeping bay views from its multi-level decks. This 6-bedroom + den, 6.5-bath residence offers more than 4,800 square feet of refined living space, blending elevated design with effortless island living. Crafted in Coastal-Tuscan style, the home showcases travertine flooring in the main living areas, warm wood flooring in the bedrooms, and soaring 10+ ft ceilings with detailed crown molding. The thoughtful layout features multiple living rooms, all ensuite bedrooms, an elevator, a morning kitchen, and a private in-law suite—ideal for hosting with comfort and privacy in mind. The chef’s kitchen is beautifully appointed with a gas cooktop, stainless steel appliances, granite countertops with breakfast bar seating, custom wood cabinetry, a walk-in pantry, oversized sink, and a dedicated bar area for seamless entertaining. Step outside and enjoy the best of the #IslandLifestyle with a private pool and spa, spacious covered and open patios, and effortless beach access just a short walk away. Perfectly positioned near Captiva Village, beloved island restaurants, and boutique shopping, this residence embraces everything that defines the #CaptivaLifestyle.

15160 Captiva Drive, Captiva
$1,500,000
2 Beds ⋅ 3 Baths ⋅ 2025023759 MLS
Fully remodeled, custom-built, and offered fully furnished turnkey, this ultimate vacation retreat captures the rare feeling of being blissfully cast away—where a long, winding driveway lined with swaying palms gently disconnects you from the outside world. Sunsets unfold beautifully over Clam Bayou with the Gulf beyond, and direct water access makes this property exceptionally special—launch a kayak or boat from your private dock and reach one of Sanibel’s most secluded beaches in minutes, a truly rare island experience. Thoughtfully rebuilt from the ground up, the home’s architecture embodies an organic coastal modern aesthetic—entirely rebuilt to perfection and stunning inside and out—with clean, intentional lines softened by warm, natural materials inspired by the surrounding coastal environment. Designed for effortless enjoyment, the property offers incredible privacy, a spacious lot approximately 360 feet in length, and mature tropical landscaping that reinforces the feeling of an instant island getaway with simple, very low-maintenance living. The backyard sparkles as the sun reflects off the Bayou waters. Inside, soaring ceilings and abundant natural light create an airy, relaxed coastal ambiance, while exceptionally refined designer finishes reflect thoughtful craftsmanship throughout. All windows and doors are impact-rated, and a commercial-grade standing seam metal roof provides lasting durability and peace of mind. A screened porch sets the stage for sunset dining, while the back deck off the kitchen enjoys prized southwestern exposure—ideal for sunbathing, entertaining, or unwinding as the day fades. Wildlife sightings are part of everyday life, from bald eagles and ospreys overhead to endless fishing just steps from your door. Blissfully secluded yet just a short bike ride to Captiva, this is a truly rare opportunity to own a refined organic coastal retreat where architecture, nature, and island luxury exist in effortless harmony.

5801 Sanibel Captiva Road, Sanibel
$1,090,000
4 Beds ⋅ 4 Baths ⋅ 2025016110 MLS
Extraordinary Sanibel Estate Home Discover a one-of-a-kind property nestled between twin ponds and pristine conservation land. Located in Sanibel’s coveted West Gulf Drive neighborhood, this serene family home offers a perfect blend of privacy, comfort, and natural beauty — all just a short stroll from a deeded beach access. The main residence features three spacious king bedrooms, including a luxurious primary suite with a private sitting room/home office, double vanity, and walk-in shower. Two additional bedrooms share a Jack & Jill bath with dual vanities and Corian countertops. A separate guest cabana, connected by a lighted and covered walkway, offers a private queen suite — ideal for visitors or extended family. It would also make a wonderful a dedicated home studio. In the main house soaring vaulted ceilings and an airy, open-plan living area lead to a sun-drenched deck — perfect for al fresco dining, grilling, or simply relaxing while watching native wildlife. The cabana pool area is a tropical oasis, with a heated pool overlooking a peaceful pond. Thoughtfully updated, the home boasts ceramic tile flooring, Corian countertops , and modern kitchen appliances including an induction cooktop and circulating ceiling fans. A tankless water heater ensures on-demand hot water, while four individual cooling systems provide custom climate control year-round. Whether you're seeking a quiet sanctuary, a multigenerational layout, or a coastal getaway with room to entertain, this property is a rare find on Sanibel Island.

2999 Twin Ponds Drive, Sanibel
$9,700,000
5 Beds ⋅ 5 Baths ⋅ 2025014681 MLS
This meticulously refined Gulf-front estate embodies the essence of tropical luxury—where timeless craftsmanship meets modern elegance. Thoughtfully enhanced over time, SOUTH HAVEN blends comfort, sophistication, and functionality at every turn. Recent updates include a redesigned kitchen and dining area, a reimagined primary bath, and a new roof (2023), along with premium finishes and fixtures throughout. The main level welcomes you with a sun-filled foyer leading to multiple guest suites, including a dual guest wing for added privacy. The chef-inspired kitchen combines contemporary design with coastal warmth, opening to a bright dining alcove ideal for gatherings. The living room frames uninterrupted Gulf views, creating a serene backdrop for every moment. Upstairs, the owner’s suite commands sweeping ocean vistas and features a stone-clad electric fireplace, woven flooring, and a tranquil, spa-like ambiance. The ground level includes a spacious garage, flexible-use spaces, and elevator access to all floors for effortless convenience. Outdoors, the estate is graced by towering Royal Palms, a resort-style pool with sun shelf, and covered lounging and dining areas designed for relaxed entertaining. Beyond the pool, a private beachside yard with manicured greens, a seaside walkway, and a charming shorefront cabana completes the coastal experience. From its refined architecture to its breathtaking sunsets, South Haven stands as a true Captiva masterpiece—where every detail celebrates the art of island living.

16770 Captiva Drive, Captiva
$6,900,000
5 Beds ⋅ 5 Baths ⋅ 225026465 MLS
Rare Beachfront Estate with Separate Guest Home on Captiva Island Seize the rare opportunity to own a private beachfront estate on the coveted Gold Coast of Captiva Island. Nestled on over an acre of land, this exquisite property features a breathtaking architectural design that seamlessly blends with nature, maximizing panoramic waterfront views and enhancing the exceptional outdoor living experience. The main home has been meticulously remodeled with high-end finishes, offering soaring beamed ceilings, an elevator, two-master suites and multiple garage spaces and storage areas. The open layout invites abundant natural light, providing an ideal setting for entertaining or relaxing with family. The separate two-bedroom guest home boasts a private lanai and its own garage, offering comfort and privacy for visitors or extended family. With 100 feet of pristine Gulf of Mexico beachfront, this estate is a rare gem on the island, situated amidst award-winning beaches. The expansive property offers unparalleled privacy and direct access to Captiva’s renowned natural beauty. Additionally, there is an exclusive opportunity to acquire the adjacent 1.4-acre bayside estate, complete with an artist’s studio, home, private dock, and pool. This additional parcel further elevates the potential of this once-in-a-lifetime property offering. Don’t miss out on this exceptional piece of Captiva Island paradise!

16886 Captiva Drive, Captiva
$33,880,000
6 Beds ⋅ 8 Baths ⋅ 224050501 MLS
Welcome to Mandalay, an unparalleled sanctuary where refined luxury meets unspoiled nature on one of Florida’s most coveted stretches of beachfront. This is more than a home, it is a legacy estate where properties of this magnitude and caliber are truly special and rare. Step inside through a grand, gated entrance and experience the seamless blend of modern elegance and timeless coastal design. Built to commercial standards in 2009, this fortress-like estate is engineered to endure with custom Tischler windows and doors imported from Germany, capable of withstanding over 200 mph winds. Every detail has been meticulously curated, far exceeding Florida’s most rigorous building codes. The estate’s expansive layout was designed for effortless entertaining and luxurious day-to-day living. The chef’s kitchen is a culinary dream, boasting a full-size walk-in cooler, professional-grade appliances, a sprawling prep island, butler’s pantry, and a stunning full-service bar, all overlooking the Gulf of Mexico’s endless horizon. It's an entertainer’s paradise, offering unforgettable backdrops for gatherings both grand and intimate. The primary suite is a haven of serenity, featuring a cozy fireplace, private balcony, and spa-inspired ensuite complete with dual vanities, individual water closets, and a spa shower that redefines relaxation. Step outside to the resort-style pool, framed by a dramatic spillover waterfall, where a private path leads you to one of Sanibel Island’s most celebrated treasures, its white sandy beach. From sunrise meditations to sunset soirées and some of the BEST shelling in the country, every moment here is steeped in the magic of Gulf-front living. Mandalay is not just a home, it’s the epitome of coastal living, elevated to its highest expression. Whether you're seeking a private family compound, an elite retreat, or a trophy property, this offering is your once-in-a-lifetime invitation to own one of Florida’s most exclusive beachfront estates. Experience the pinnacle of privacy, prestige, and paradise... Mandalay awaits.

6111 Sanibel Captiva Road, Sanibel