Captiva Single Family Homes For Sale - 5 homes

Remarks: Presented with a new design vision by MHK Architecture, this extraordinary Captiva Island estate features concept plans to reimagine the existing residence, design a new coastal masterpiece, or expand by combining with the adjacent 1.5-acre estate lot to create a contiguous 5-acre compound unlike anything else on Captiva Island. A once-in-a-generation opportunity to own one of the island’s largest and most private bay front properties - 3.5 acres of gated serenity with deepwater access, resort-style amenities, and exceptional privacy along the coveted Roosevelt Channel. Surrounded by unspoiled nature, the property offers direct Gulf access with private docks. Inside, the existing custom-built home showcases soaring beamed ceilings, rich wood flooring, and a dramatic beacon tower filling the great room with natural light. Thoughtfully designed for entertaining and easy island living, it offers a chef’s kitchen, formal dining, wood-accented den, private study, and flexible guest quarters. Two grand ensuite bedrooms serve as luxurious sanctuaries, complemented by an indoor wellness wing with travertine-lined pool, fitness room, and sauna. Outdoors, enjoy a tennis court, bocce court, firepit overlooking the bay, and a rooftop hot tub for starlit evenings. A three-car garage with workshop provides ample space for vehicles, storage, and all your waterfront essentials. With no HOA restrictions, the estate offers remarkable flexibility - whether envisioned as a family legacy compound, private coastal retreat, or trophy property of architectural distinction- where architectural vision meets natural beauty.

Listing is courtesy of: DOUGLAS ELLIMAN FLORIDA,LLC (239-799-5300)

Listing Agent: Brittany Skotak, Pa (239-290-5409)

Remarks: High-performing Vacation Rental Getaway! Must see this extraordinary Key West-style retreat built in 2021, perfectly positioned on Upper Captiva Island’s private airstrip. Designed for discerning buyers who value both refined living and adventurous access, this elevated luxury home offers a rare opportunity for pilots and island enthusiasts alike. Accessible only by boat, ferry, or private aircraft, Upper Captiva is a hidden gem where pristine beaches, unspoiled nature, and ultimate privacy define the lifestyle. This stunning three-bedroom, three and a half-bathroom residence was expertly constructed on pilings with a metal roof and impact-resistant windows and doors, ensuring strength, safety, and peace of mind. The living space remained untouched by recent storm surge events, a testament to its thoughtful design and elevation. Inside, vaulted ceilings and a striking clerestory window system flood the home with natural light, creating a bright, breezy ambiance that complements its coastal surroundings. Expansive Gulf and bay views can be enjoyed from the open-air balcony and patio—ideal for relaxing or entertaining guests. The chef’s kitchen is equipped with high-end appliances, including a propane-fueled range with grill, and double oven, tailor-made for culinary enthusiasts. Each of the three spacious bedrooms features its own private en-suite bath, offering comfort and privacy for residents and guests, and additional sleeping space area. Outdoors, a heated saltwater pool and spa invite relaxation, enhanced by a fully automated system controllable remotely via smartphone app—perfect for preparing your soak before you arrive. The pool deck is finished with elegant pavers, while the composite decking on the screened porch and upper balcony offers durability and low maintenance in key outdoor living spaces. Down by the pool, a sandy beach lounge area and an undercover recreation space (which is also an open air hangar) provide a perfect setting for island-style entertainment and relaxation. An outdoor kitchen and a fire table adds ambiance for cozy evenings under the stars. Located just 650 feet from the white sandy beach, this home offers both convenience and tranquility and front-row seats to some of Florida’s most breathtaking sunsets. Each evening, the sky transforms into a vibrant canvas of oranges, pinks, and purples, casting a golden glow over the shoreline and surrounding palm trees. Whether you’re swimming, sunbathing, or strolling the shore, the beach is always within reach. For investors, this property doubles as a proven income generator with a successful short-term rental history and records available upon request. 4540 Seair Lane is more than a home—it’s a lifestyle. A rare find for American and international buyers alike, it combines modern luxury with island seclusion and aviation access. Discover the ultimate island escape on Upper Captiva, where every detail is elevated, and every arrival feels like a getaway.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Carleen Murone (239-223-9454)

Remarks: This beautiful home features a stunning entrance under an old Live Oak tree and tropical foliage. Know as the Paddle to the Sea cottage, the entrance is a classic split foyer, with steps down to 4 bedrooms, 2 baths and guest living area. Step up and open to a dramatic Great Room with vaulted and coffered ceiling, kitchen, bar and half bath. Multiple classic multi-lite French doors along 3 sides open up the outdoors, while screened decks surround both the first and second floors providing comfortable and spacious outdoor living. A corner stairwell then provides access to the third-floor master suite and living area. Enter this ultimate private suite and Stunning views open up across Boca Grande Pass and Charlotte Harbor and to Boca Grande. A private balcony facing north provides unsurpassed privacy and beauty. Beneath the first living floor is a fully screened and decked area for golf cart parking, work room, spare fridge and freezer, ping pong table, storage or whatever, It is spacious, protected multi-use space. Access is via a stairwell to the first floor and a ground level automatic garage door for cart access. The home is in new condition, following significant reconstruction after Hurricane Ian in 2022. This effort brought the entire structure up to current building and windstorm codes with new roof strapping and roof, all impact glass, interior finishes, appliances, whole house generator and too much to summarize here. Refer to the supplementary information tabs for complete details of the work accomplished. As far as flood threats are concerned, the home is in the X Zone, above any potential storm surge or flooding. Home buyers on bridgeless Useppa Island are required to have membership in the Useppa Island Club and Marina. Useppa is a luxury boating, fishing private resort in the style of Olde Florida. No cars, just golf carts, bikes and feet for transport. Boat Dockage is available at the Marina. The island is just 3 miles south of Boca Grande and a 15-minute boat ride to Pine Island and all things “mainland”.

Listing is courtesy of: UIP PROPERTY COMPANY LLC (239-410-7850)

Listing Agent: Brian Mccolgan (239-410-7850)

Remarks: Located on the eastern shore of the reimagined and redeveloped private Useppa Island, the Aerie estate is the signature property on 30 miles of Pine Island Sound. With 250 feet of shoreline and views that capture 180 degrees of the Sound stretching for miles, the home is unique. Enter the foyer and take in a great room reminiscent of a century old fishing retreat, the pecky cypress ceiling soaring 25 feet above the fireplace gathering area, broad windows to watch passing boats and soaring birds. A mezzanine floor overlooking the great room boasts a kitchen with two of everything and room for multiple chefs-or dishwashers or bartenders. Overlooking the water from this level is a dining room for 12. Adjacent to the kitchen is a screened-in grilling and outdoor serving area, and a swimming pool with an expansive deck area. Also on this level is a half bath, and 2 bedrooms with ensuite baths. The second floor includes 2 bedrooms with ensuite baths and a massive 25x30 owners suite. A private dock, enclosed and conditioned garage, storage and equipment rooms provide the service areas needed to serve this expansive home. Useppa has all the services and amenities of a small town, and is a bridgeless island ensuring privacy and solitude. Yet an active lifestyle of boating and sporting activities for any that wish to participate. The island is known for its outgoing community of residents, and with only 118 homes, the nature of the island will not deviate from the tropical luxury and Old Florida ambiance that create this special place in the sun.

Listing is courtesy of: UIP PROPERTY COMPANY LLC (239-410-7850)

Listing Agent: Brian Mccolgan (239-410-7850)

Remarks: Coves Edge is an elevated luxury retreat on coveted Useppa Island in the aquatic preserve of Pine Island Sound. Sitting well above the flood zone, this updated 5BR/5+2 BA home offers long water views, lush privacy, and exceptional amenities. Enjoy 97’ of waterfront with sand beach and riparian rights, plus a private dock with two lifts and additional space for a larger boat. A 40’ lap pool with expansive decking overlooks the Sound, surrounded by mature landscaping on one of the highest elevation points in Lee County. Interiors blend contemporary updates with Old Florida charm. Light-filled principal rooms capture stunning views throughout. The main-floor primary suite includes views of the Sound, an ensuite, walk-in closet and a private staircase to two offices/studios and multiple furnished outdoor retreats. Spacious water view kitchen with Sub-Zero fridge, double ovens, and new custom cabinets and stone countertops. Upper level offers two king guest suites with soaring ceilings, dedicated baths, and access to a 670 SF Sound-view deck and a 225 SF front deck overlooking the Useppa Palm Garden. Lower level includes a queen suite and a 4-twin bunk room for guests. Whole-home generator, hurricane protection, new AC equipment with a dedicated mechanical room and a separate golf cart garage and workshop. Offered turnkey with golf cart and most furnishings. Perfect for seasonal or full-time island living with excellent rental opportunities. Located on the southern end of the island, along the historic Pink Path and overlooking the Sound, you can keep an eye on your boat at the dock just behind the house. Coves Edge cottage is in the boating community of Useppa Island. The 110-acre Sanctuary is a private community and members-only club. With no need for gates or walls, it is surrounded by water, in the pristine Pine Island Sound and Charlotte Harbor aquatic preserves. Geographically it is in the same chain of barrier islands as Sanibel-Captiva, visible to the south, although one island east of the Gulf of America. Accessible only by boat (or aircraft), the commute to the mainland is in a special class of its own. Just a 15-minute joyful boat ride will deliver you to Boca Grande or Pine Island, and thence to all “civilized” conveniences of the mainland. The commute is special in a way that you will never tire of it. Just think-you are not stuck in traffic, or waiting for a light to change, fretting over the packed roads ahead. You are just watching the dolphins play and the birds dive, waving to passing boats with smiling passengers. Yes, not like the mainland! You might be sitting next to one of your Useppa neighbors, who has all their goods delivered to the Shore Port, where the staff will transport them to the island, and her home. Who said it is inconvenient when you don’t have roads? And this beautiful home will let you join the ranks of the smart and lucky who have already landed on Useppa as a lifestyle choice.

Listing is courtesy of: UIP PROPERTY COMPANY LLC (239-410-7850)

Listing Agent: Brian Mccolgan (239-410-7850)