High-End Real Estate For Sale in Upper Captiva, FL

High-performing, income-producing vacation rental on one of north captiva island's premier streets. Privately nestled among mature tropical landscaping, this beautifully maintained 4-bedroom, 3.5-bath island retreat offers over 2, 300 sq ft of thoughtfully designed living space and a proven history of strong rental performance. Guests are drawn to the resort-style outdoor living, featuring an exceptionally large private pool, hot tub and outdoor shower, multiple entertaining areas, and a spectacular southwest-facing third-floor lanai that fully opens to the living room, creating a seamless indoor/outdoor living experience. Two en-suite bedrooms, a bunk room with a third bath, and a fourth queen suite provide ideal accommodations for owners and guests alike. Recent upgrades include hardie plank siding, two hvac systems, trex decking, a brazilian hardwood pool deck, a cargo/luggage lift, and a paver driveway. A rare opportunity to own a turnkey island property that combines exceptional rental income, lush tropical privacy, premium outdoor amenities, and one of north captiva's most desirable locations.

Elevated living, gulf views & rooftop sunsets imagine pulling up in your golf cart, the breeze already shifting as you arrive at a home set high and dry in one of north captiva's most sought-after neighborhoods. 4510 oyster shell dr is a 3-bedroom, 2.5-bath retreat with an additional 4th sleeping room, designed to make the most of island life. The reverse floorplan captures gulf views and coastal light from the moment you step into the main living level. Upstairs, the open-concept living, dining, and kitchen area feels bright, easy, and inviting—perfect for gathering after a day at the beach or hosting friends for a laid-back island evening. Large windows and elevated positioning bring the outdoors in, while the surrounding landscape and water views remind you exactly why you're here. And just down the sandy lane lies one of the island's true treasures—a premier beach access point leading to north captiva's widest stretch of powder-soft, sugar-white sand. This is the kind of beach people travel across the world to find—expansive, uncrowded, and endlessly walkable—where mornings begin with quiet shoreline strolls and evenings end with unforgettable gulf sunsets. Then there's the rooftop lookout—one of those features that quietly becomes your favorite place. Morning coffee surrounded by water views as the island wakes up… sunset cocktails as the sky turns gold… and quiet nights under a blanket of stars with the preserve stretching out below. Recent upgrades, including a new metal roof, hardie board siding, and aluminum railings, add both durability and a clean coastal finish. Positioned along one of the island's highest ridgelines—with elevated construction and storm shutters—the home offers an added sense of confidence and comfort. This isn't just a vacation home—it's a place where beach days feel effortless, sunsets feel personal, and every visit makes it harder to leave. Come see it for yourself—and picture where your mornings, beach walks, and next chapter could begin.

A must see! Great opportunity. North captiva, private heated saltwater pool, gulf-side location, turnkey furnished, rental history and 150+ five-star guest reviews. 64k in rentals in 2026 alone to date! Welcome to “the perfect shell, ” a fabulous turnkey island beach home offering an exceptional south gulf-side location, private heated saltwater pool, easy beach access and impressive vacation-rental history with 150+ five-star reviews! Situated on a desirable high-and-dry lot in captiva dunes, this charming stilt home is just a short walk or golf-cart ride to the wide sugar-sand shoreline of sunset beach, known for spectacular sunsets, shelling, fishing, swimming and sandbars. Additional prime surrounding lots may be available for purchase by the buyer, offering a unique opportunity for added privacy or expansion. Strap: 05-45-21-08-00000.0350 & 05-45-21-08-00000.0090 inside, a bright, open great-room floor plan captures beautiful tropical views and opens to an expansive screened front balcony with sliders, ceiling fan and recessed lighting. The home offers 2 bedrooms and 1.5 baths and is sold turnkey furnished with lovely furnishings, fixtures and window coverings. The kitchen features a long breakfast bar, corian countertops, recessed lighting, appliances and gas range. The primary bedroom includes a large closet. The main bath offers a large tiled shower and corian-topped vanity. The half bath includes a sink, extensive built-in cabinetry, countertops and full-size stacked washer/dryer, with potential for a second full bath if desired. Outside, the large heated saltwater pool features built-in seating shelves, aluminum fencing and expansive brick-paver decking with wonderful sun exposure. A generous side yard provides additional outdoor space and room to expand. The spacious under-house area offers even more possibilities for entertaining—add an outdoor shower, changing area, bath, bar or outdoor kitchen. Enjoy the best of island living with exceptional outdoor space, tropical surroundings and easy access to one of north captiva’s most beautiful beaches. Great property layout with a large side yard, pool area and room to expand—an increasingly special combination on the island. Simply a must-see! Recent improvements and features include a 2024 white standing-seam metal roof, 2023 hvac, 2025 exterior paint, 2023 whole-house reverse-osmosis system, hurricane-impact windows and doors, hardie-board siding, tile throughout and attached ground-level garage. For buyers interested in vacation-rental income, the perfect shell has an established rental history with many repeat annual guests. The property is professionally managed, with continued management available. Best of all, this is a private pool home with no hoa fees or club membership to assume! Whether you're looking for your own north captiva getaway, an established vacation-rental property, or a combo of personal enjoyment & income potential. Exceptional location.

Dock your boat and enjoy water views from an end-unit townhome, while you build your dream home on an incredible lot with direct views toward the beach and gulf! Introducing a unique island ownership combination: townhome #60 at 370 townhouse ln (parcel id: 05-45-21-03-00000.0600) in safety harbor club, paired with a separate buildable homesite at 4580 oyster shell dr, offered together as an exceptional package. The townhome offers immediate enjoyment with beautiful harbor views, shared community dockage steps away, and full access to all safety harbor club amenities, including a heated pool, tennis courts, pickleball, clubhouse, dining, convenient ferry landing, and private gulf beach access. Perfectly positioned within safety harbor club, the townhome provides an ideal home base for boating, beach days, and island living, with rental or personal-use flexibility. Included in this package is 4580 oyster shell dr, a valuable homesite with incredible views! You will be stunned by the amazing view corridor looking down onto the sugar-sand beach and sparkling gulf waters beyond. Imagine watching the sun set every night right from your living room. This lot plus townhome combination is a must-see!

Expansive & panoramic gulf views with the beach just steps away! This soaring 4 bedroom and 3 bath estate home offers hardie board siding, aluminum railings, and impact windows. The reverse floorplan creates fantastic views from every corner of the living spaces, indoors and out. Imagine relaxing on the 2nd level porch or 3rd-floor mezzanine, gazing at the incredibly scenic coastline of cayo costa. The top level could be a fifth sleeping space or your favorite sunset-watching room. Custom kitchen with stainless steel appliances and formal dining nook surrounded by windows. The first-story covered screen porch has excellent gulf views from the master suite and largest guest bedroom. Heated pool and extensive deck space. Great for dining and entertaining. This property includes a nearby beachfront parcel and a deeded walkway easement for a sandy path to your private gulf beach. A wide-view easement over the adjacent beachfront property to the west also helps to maintain your view over time. The location, number of sleeping areas, pool, and very special view give this home excellent rental potential. To complement this outstanding home, a valuable dock slip is available in the nearby boat basin for an additional price of $200k with the house. Furthermore, the adjacent beachfront lot to the west can also be available for purchase to connect this home all the way to the water.

Not everyone can get here… and that’s exactly the point. Indiana jones adventure meets luxury island living | rare fly-in / boat-in captiva estate. Set along the waters of pine island sound with views to the gulf of america, this extraordinary upper captiva property offers one of the most unique lifestyles in southwest florida. Located on approximately 1.16 acres, this private island retreat is accessible by boat or private aircraft via salty approach airstrip (fl90), upper captiva’s private 1, 800-foot grass runway. The property also includes a hangar below the home, making it ideal for aviation enthusiasts. Fl90 is best suited for experienced pilots flying light aircraft designed for short-field and turf operations, including planes in the style of cessna 150, 152, 172, 182, 206, piper cub, super cub, aviat husky, maule, kitfox, and similar stol-capable aircraft. For seaplane owners, welcome home. The residence features 5 bedrooms, 5 bathrooms, and over 3, 900 square feet designed to capture panoramic water views and sunsets. A private elevator services all four levels. Inside, the home offers spacious living and entertaining areas with marble, tile, and wood flooring throughout. The chef’s kitchen includes premium appliances, wine and beverage refrigeration, ice maker, and an open layout ideal for hosting. Outdoor living is exceptional, with expansive terraces and gathering spaces overlooking the water. A new trex waterfront deck leads to a private composite dock with boat lift, ideal for a 40-foot viking for serious fishing adventures, plus a fast boat such as a nortech or midnight express for island-hopping and cruising. The dock may also accommodate a seaplane. Additional features include whole-house generator, hurricane impact windows and doors with shutters, outdoor kitchen, poolside cabana, exercise room, multiple entertaining spaces, and well water, septic, and propane gas service. A rare combination of privacy, adventure, and luxury waterfront living in one of southwest florida’s most exclusive island communities. Created for those who crave privacy, adventure, and a true sense of escape, this estate offers a lifestyle few properties can match. Spend your mornings heading out by viking for serious fishing, your afternoons cruising by fast boat to nearby islands, and your evenings enjoying panoramic sunsets over pine island sound. With a hangar below the home, private dockage, expansive terraces, and resort-style outdoor living, every detail supports an effortless fly-in, boat-in island lifestyle. This is more than a residence. It is a gateway to one of the most extraordinary waterfront experiences in southwest florida. With exceptional access to boca grande’s renowned deep-water fishing right from your back door, this remarkable estate is designed for the buyer who expects the extraordinary. Complete with a private sauna and every luxury appointment. The 29'5" x 36'7" hangar-style garage offers substantial space for aircraft.