Upper Captiva Homes with None Waterfront type

Upper Captiva Homes with None Waterfront type

Welcome to Upper Captiva, a hidden gem nestled in the heart of Lee County, Florida. This idyllic island community offers a unique blend of tranquility and natural beauty, making it the perfect retreat for those seeking a serene escape from the hustle and bustle of everyday life.

Upper Captiva is renowned for its charming homes, each thoughtfully designed to harmonize with the stunning surroundings. With none waterfront properties, you can enjoy the peace and privacy of your own oasis while still being just a stone's throw away from the beautiful beaches and crystal-clear waters of the Gulf of Mexico. These homes boast spacious layouts, modern amenities, and lush landscapes, providing an ideal setting for families, couples, or anyone looking to bask in the warm Florida sun.

The community is accessible only by boat or ferry, ensuring a sense of exclusivity and seclusion. Residents and visitors alike can explore the island's pristine beaches, indulge in water sports, or simply unwind on their private decks, soaking in the breathtaking sunsets. Upper Captiva's vibrant wildlife and natural ecosystems invite outdoor enthusiasts to hike, bike, and discover the rich biodiversity that makes this area so special.

Whether you're searching for a permanent residence or a vacation getaway, Upper Captiva offers a unique lifestyle that celebrates nature and community. Discover the charm of this exquisite island and find your dream home in Upper Captiva, where every day feels like a vacation. Come and experience the magic of island living!

Newest Upper Captiva Homes with None Waterfront type

4471 Smugglers Dr, Captiva
$130,000
2026033875 MLS ⋅ Upper Captiva BLDG.
SOUTHERN EXPOSURE AND THE OPPORTUNITY TO BUILD YOUR OWN ISLAND ESCAPE IN CASTAWAY KEY. Located on Upper Captiva, this homesite offers a great setting to design a custom home tailored to the relaxed Southwest Florida lifestyle. Southern exposure is ideal for enjoying abundant sunshine throughout the day and creating an outdoor living area that makes the most of the island setting. Whether you are planning a personal getaway, full time residence, or investment property, this lot gives you the flexibility to bring your vision to life. Spend your days enjoying the beach, boating, fishing, shelling, and everything that makes Upper Captiva such a unique destination. With a peaceful tropical atmosphere and the charm of Castaway Key, this is a great opportunity to create a home and lifestyle that feels like a true island retreat.

4471 Smugglers Dr, Captiva
4520 Smugglers Dr, Captiva
$130,000
2026033871 MLS ⋅ Upper Captiva BLDG.
CASTAWAY KEY ISLAND LIVING STARTS HERE. This homesite on Upper Captiva offers the perfect opportunity to build your own private island retreat in the desirable Castaway Key community. Surrounded by the natural beauty and relaxed atmosphere that make Upper Captiva so special, this lot provides an ideal setting for a custom full time residence, vacation getaway, or investment property. Enjoy the unique island lifestyle with beautiful Gulf beaches, boating, fishing, shelling, and unforgettable sunsets all close by. With its tropical surroundings and peaceful setting, this property is a blank canvas ready for your vision. Build the home you have been dreaming of and create your own slice of paradise in Castaway Key on Upper Captiva.

4520 Smugglers Dr, Captiva
4481 Butterfly Shell Dr, Captiva
$974,500
2 Beds ⋅ 1.5 Baths ⋅ 2026029804 MLS ⋅ Upper Captiva BLDG.
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.

4481 Butterfly Shell Dr, Captiva
120 Swallow Dr, Captiva
$1,125,000
5 Beds ⋅ 3.5 Baths ⋅ 2026026019 MLS ⋅ Upper Captiva BLDG.
Exceptional opportunity to own a beautifully renovated 5-bedroom, 3.5-bath island retreat just a short walk from the pristine Gulf beaches of North Captiva Island. Offering 1,682 square feet of living space, this coastal home combines modern updates with the relaxed island lifestyle that makes North Captiva one of Southwest Florida's most unique destinations. Accessible only by boat or private aircraft, North Captiva offers miles of uncrowded beaches, world-class fishing, breathtaking sunsets, and a peaceful atmosphere free from cars and traffic. Thoughtfully designed to accommodate large families and guests, the home offers plenty of space to spread out across multiple living areas and outdoor gathering spaces. The main level features a king primary suite with private ensuite bath, a queen guest bedroom, and a custom bunk room with four twin beds. The lower-level in-law suite provides exceptional flexibility with a king bedroom, a bedroom with two twin beds, a second living area, kitchenette with sink and microwave, and a full bath, making it ideal for extended family, guests, or vacation rental accommodations. Every level of the home features decks and outdoor living areas, including two screened porches with overhead fans for enjoying island breezes year-round. The crow's nest rooftop deck offers stunning 360-degree views of the island, Gulf waters, and unforgettable sunrises and sunsets. Extensive recent improvements include a new roof, new siding, updated electrical, new water system, new hot water tank, fresh interior and exterior paint, new decking, a newly constructed crow's nest, rescreened porches, updated landscaping and driveway improvements, new poly outdoor furnishings, luxury vinyl plank flooring, tile flooring, and granite countertops in the bathrooms. Currently operating as a successful vacation rental, this property offers outstanding income-producing potential while also serving as the perfect private island getaway. Two golf carts are included for convenient transportation throughout the island. Whether you're seeking a personal retreat, full-time residence, or established investment property, this exceptional North Captiva home is ready to be enjoyed.

120 Swallow Dr, Captiva
4521 Oro Pesos Ln, Captiva
$170,000
2026013740 MLS ⋅ Upper Captiva BLDG.
Here's your opportunity to own a piece of one of Southwest Florida's most coveted private islands. This vacant lot on Oro Pesos Lane offers a clean slate to build your custom island retreat on North Captiva — a boat-access-only barrier island where the pace slows, the crowds disappear, and the Florida you've been searching for actually exists. No bridge. No cars. No worries. North Captiva is one of the last truly undeveloped islands in Lee County, and this lot sits in the desirable Jose's Hideaway section of the island — walkable to the beach at the end of the street and close to all island amenities. Whether you're envisioning an elevated coastal home, a private fishing retreat, or a high-performing vacation rental, this lot delivers the fundamentals: a prime island address, a natural setting, and the kind of scarcity that protects long-term value. The adjoining lot is also available — purchase both together to double your property size and create nearly a half-acre parcel. Build a private compound, a main home with a guest house, or two separate income-producing properties with their own distinct addresses and street access. Opportunities like this simply don't exist on North Captiva. Short-term rental demand on North Captiva is strong and new construction commands premium nightly rates. Details on the building process, preferred island contractors, and revenue potential are available upon request

4521 Oro Pesos Ln, Captiva
Captiva
$150,000
222078159 MLS ⋅ Upper Captiva BLDG.
Amazing opportunity to build your dream vacation paradise. Arrive by sea or air to your private home in Upper Captiva island. Just steps away to multiple beach access areas and an abundance of preserve land to explore. This piece of paradise will afford a perfect setting for nature enthusiasts.

Captiva
4440 Oyster Shell Dr, Captiva
$150,000
222078161 MLS ⋅ Upper Captiva BLDG.
Amazing opportunity to build your dream vacation paradise. Arrive by sea or by air to your private home in Upper Captiva island. Just steps away to multiple beach access areas and an abundance of preserve land to explore. This piece of paradise will afford a perfect setting for nature enthusiasts.

4440 Oyster Shell Dr, Captiva
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