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16814 Captiva Drive, Captiva
$13,500,000
5 Beds ⋅ 8 Baths ⋅ 2026047820 MLS
Some properties impress you. Others stay with you. On Captiva's Gold Coast, this one-of-a-kind beachfront estate has an identity all its own. A treasured 1912 beach cottage and a striking contemporary guest residence share 131 feet of Gulf frontage, creating a deeply personal retreat with remarkable architectural character. Originally built on Useppa Island and brought to Captiva in 1948, the cottage has been reimagined by architect Joyce Owens, with eclectic details, subtle industrial touches and the warmth of vintage Captiva. Two bedrooms plus a den, a fireplace, Gulf-facing kitchen and shaded terrace make it easy to feel at home. Designed by Owens and built by Benchmark Construction, the newer guest residence expands the owners' living and entertaining experience. Shared materials and custom details connect the homes, while soaring ceilings, exposed trusses and ductwork, distinctive lighting and expansive glass give the newer residence a dramatic presence. Two pavilions joined by a covered breezeway offer generous living areas, kitchens and space for family and friends. A pool and spa and covered dining terrace with an outdoor kitchen overlooking the cottage and Gulf bring island living into every gathering. Intimate in feeling and expansive in the way it lives, the estate brings history, design and beachfront living together in a way that feels entirely its own. An exceptional Captiva offering for someone seeking a home as individual as they are.

16814 Captiva Drive, Captiva

15155 Wiles Drive, Captiva
$1,895,000
3 Beds ⋅ 2 Baths ⋅ 2026047375 MLS
Beautiful beach Cottage located in Captiva's "Village just steps from the beach! Wonderful 3 bedroom, 2 bath home with a heated and fenced pool situated on a corner lot. Open and flowing floor plan with a great room, engineered hardwood floors throughout, plantation shutters and an open kitchen and dining room. Perfect for entertaining friends and family. The kitchen offers stainless steel appliances and is fully equipped. Split floor plan with spacious bedrooms and baths. There is an outside shower for rinsing off after a day at the beach and a shaded shell cleaning station. Home is being sold fully furnished. Great opportunity for a rental investment property or a personal tropical retreat. Shopping and restaurants are just a short walk or golf cart ride away. Enjoy the marina for boating and fishing, the historic Chapel By the Sea, the library and miles of bike paths.

15155 Wiles Drive, Captiva

4172 W Gulf Drive, Sanibel
$3,495,000
4 Beds ⋅ 4 Baths ⋅ 2026044706 MLS
Experience exceptional coastal living in this stunning 2024-built residence on Sanibel's desirable West Gulf Drive, just across the street from the beautiful Gulf beaches. Thoughtfully designed with sophisticated finishes and effortless indoor-outdoor living, this elevated 4-bedroom, 4-bath home offers the perfect blend of modern luxury and island charm. Step inside to discover a bright, open-concept interior featuring luxury vinyl plank flooring, elegant coastal finishes, and a striking shiplap accent wall with a sleek electric fireplace. The spectacular gourmet kitchen serves as the heart of the home, showcasing an expansive quartz-topped island with seating, custom white cabinetry, a decorative tile backsplash, stainless steel appliances, a statement range hood, and stylish woven pendant lighting. A spacious dining area surrounded by windows creates an inviting setting for gatherings, while sliding glass doors open to a covered lanai overlooking the tropical surroundings. The generous primary suite offers a peaceful retreat with a spacious bedroom, walk-in closet, and beautifully appointed ensuite bath. Three additional bedrooms and bathrooms provide comfortable accommodations for family and guests. A dedicated laundry room and ample storage add everyday practicality. Step outside to your own private tropical oasis, where an expansive screened pool enclosure surrounds a sparkling swimming pool, generous paver deck, and multiple areas for lounging and entertaining. The covered outdoor living area provides a shaded retreat, while the impressive outdoor kitchen features a stainless steel grill, pizza oven, beverage refrigerator, and ample counter space, perfect for hosting poolside gatherings or enjoying casual island evenings. The ground level also offers generous garage parking and additional storage. Built in 2024 with impact-resistant windows and doors, this exceptional residence combines modern construction with timeless coastal appeal. Ideally located just steps from the beach, enjoy morning shelling, leisurely shoreline strolls, and the natural beauty that makes Sanibel Island so special. Whether you're seeking a luxurious full-time residence or an unforgettable island escape, this remarkable West Gulf Drive home delivers the ultimate Sanibel lifestyle!

4172 W Gulf Drive, Sanibel

15361 Captiva Drive, Captiva
$3,820,000
5 Beds ⋅ 5 Baths ⋅ 2026024624 MLS
Steps from the Gulf, this beautifully appointed 5-bedroom, 5-bath home known as Almost Heaven sits along the desirable Tween Waters stretch in the heart of Captiva Village, offering the island’s best combination of location and livability. This residence delivers turquoise-water views and puts you a minute’s walk from the Village’s boutiques and galleries. Deeded beach access adds an extra layer of convenience and long-term value. A dramatic two-story great room anchors the main living space, complemented by a formal dining area perfect for hosting family dinners or entertaining guests. The gas fireplace adds warmth and ambiance on cooler evenings, while the chef’s kitchen brings it all together with an oversized refrigerator, glass cooktop, built-in microwave, wine cabinet, and premium cabinetry. Thoughtfully designed for gathering, the home sleeps up to 14. The primary suite is complete with a morning bar and beverage cooler, a jetted soaking tub, and an oversized dual-spray walk-in shower. Two additional king suites, a queen bedroom, and a built-in bunk room complete the sleeping arrangements. This home is ideal for multigenerational living or hosting extended family and friends. Outdoor living centers on a private heated pool with a spa and an adjacent putting green, surrounded by lush, mature tropical landscaping for total privacy. Extensive recent upgrades bring peace of mind and easy living, including a brand new metal roof, impact windows and doors, an elevator, garage doors, pool equipment, and air conditioners, plus newly installed EnduraFlood paneling on the ground level. Whether as a personal retreat or a strong income-producing investment on one of Southwest Florida’s most sought-after barrier islands, Almost Heaven offers a rare blend of privacy, proximity to the beach, and Village walkability that’s difficult to replicate.

15361 Captiva Drive, Captiva

Sanibel
$1,995,000
3 Beds ⋅ 5 Baths ⋅ 2026044531 MLS
Riverfront tranquility meets beachside living at this custom-designed, three-bedroom, four-and-a-half-bath residence with a dedicated office, private pool and spa, and expansive outdoor living spaces. Set along the Sanibel River and directly across the street from the beach, this concrete-construction home is framed by lush tropical landscaping. A sweeping paver driveway, tiled roof, and graceful entry staircase create a memorable welcome. Inside, marble floors, arched openings, detailed ceilings, and decorative glass bring character to the spacious layout. The central living room features a wood-burning fireplace, while a separate formal dining room provides an elegant setting for entertaining. The office offers rich custom cabinetry, built-in shelving, and an integrated desk. The well-appointed kitchen features stainless steel appliances, double wall ovens, custom cabinetry, granite countertops, a breakfast bar, and pantry storage. An adjoining breakfast nook overlooks the outdoor living area, while a separate wet bar with glass-front cabinetry, a wine cooler, and an ice maker keeps entertaining effortless. The kitchen opens to a generous family room with a custom entertainment center, tray ceiling, and sliding glass doors framing peaceful river views. Privately positioned on its own side of the home, the primary suite offers a spacious sitting area, direct access to the covered lanai, and multiple closets. Its inviting bath features dual vanities, a dressing table, a soaking tub beneath arched windows, and a separate walk-in shower. Two guest bedrooms occupy the opposite wing, creating comfortable separation for family and visitors. Covered outdoor living areas extend across the rear of the home, offering room to lounge, dine, and enjoy the waterfront setting. A built-in outdoor kitchen with a gas grill, sink, and refrigerator makes alfresco meals easy. Below, a spacious screened enclosure surrounds the heated pool and raised spa, with a paver deck and tropical landscaping overlooking the river. From quiet mornings watching the water to afternoons by the pool and sunset walks on the beach, this home brings the island lifestyle beautifully into focus.

Sanibel

13230 Linton Road, Fort Myers
$8,500,000
4 Beds ⋅ 6 Baths ⋅ 2026033951 MLS
More than a waterfront home, this extraordinary gated estate spans roughly 2 private acres along the Caloosahatchee River, combining panoramic sunset views, quick Gulf access, a natural lagoon flowing beneath the residence and Caribbean-Coastal inspired luxury in a setting unlike anything else on the Fort Myers waterfront. A long, winding, palm-lined drive introduces a rare sense of privacy and scale close to town. Surrounded by lush tropical grounds and water on multiple sides, the property features a natural cut from the river that travels alongside and beneath the home, creating a secluded lagoon-like environment reminiscent of a private island retreat. Completely redesigned by Clive Daniel, the residence pairs exceptional craftsmanship and refined materials with comfortable, casual luxury. All-concrete construction and weather-resistant materials provide a substantial foundation for waterfront living. European white oak floors, soaring beamed ceilings and walls of glass fill the interiors with natural light while maintaining a constant connection to the river. The expansive great room offers a fireplace, multiple gathering areas, generous dining space and remarkable water views. The chef’s kitchen features state-of-the-art appliances, an oversized gathering bar and a separate full-service prep kitchen with additional ovens, refrigeration and cabinetry, ideal for entertaining or catered events. The impressive primary suite is a private waterfront sanctuary with dramatic ceilings, a spacious sitting area, dual walk-in closets with custom built-ins and a luxurious bath with separate vanities, shower and soaking tub. Generous, privately positioned guest suites each feature an en-suite bath, with two enjoying beautiful water views. Balconies and terraces extend the living spaces outdoors, including a large screened patio and two spiral staircases leading to an expansive rooftop sun deck with commanding river and sunset views. A resort-style pool and spa are surrounded by tropical landscaping and generous outdoor entertaining areas. Beneath the residence, the sheltered lagoon and extensive dock space offer exceptional potential to create the ultimate setup for yachts, fishing boats and personal watercraft. Automobile enthusiasts will appreciate the existing 4 to 6-car garage, providing substantial space for a prized collection and additional storage. The estate also offers tremendous flexibility for future expansion, whether envisioned as an addition to the primary residence, guest house with additional garage space, tennis or pickleball court, or private recreational compound, subject to applicable approvals. Private yet convenient to downtown Fort Myers, Bonita, Naples, beaches, dining and entertainment, with the bay, Gulf and barrier islands quickly accessible by boat. This is a singular waterfront estate defined by land, water, privacy, architecture and possibility.

13230 Linton Road, Fort Myers

3767 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

15160 Captiva Drive, Captiva
$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

17170 Captiva Drive, Captiva
$3,250,000
2 Beds ⋅ 2 Baths ⋅ 223036615 MLS
Own this little adorable Captiva beach cottage OR "IMAGINE" and build something incrediably special like the coastal modern masterpiece shown. Displayed are Conceptual renderings of what you could build on this property. You get to decide! Enjoy this adorable beach cottage or build a new coastal modern "Landmark" getaway. Whats offered at this price is this charming seaside retreat showcases a open layout w/expansive glass sliders that open onto a large deck, offering breathtaking views of the Gulf of Mexico. Nestled just steps away from the Blind Pass bridge, where Sanibel/Captiva converge, Coquina Cottage proudly stands as the first residence on Captiva beach, establishing itself as a landmark destination. With its panoramic beach views, this idyllic getaway boasts a compact yet well-equipped kitchen, two cozy sleeping areas, & a soothing spa. Set on a half-acre waterfront property w/a single dwelling along the Gulf, the cottage is enveloped by tropical native vegetation. Enjoy exceptional fishing, observe marine life & wildlife, indulge in world-class shelling, & enjoy enchanting sunsets on the white sand beach of Captiva.

17170 Captiva Drive, Captiva

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