Upper Captiva Homes with Boating Amenities

Upper Captiva Homes with Boating Amenities

Welcome to Upper Captiva, a hidden gem nestled in the heart of Lee County, Florida. This enchanting island paradise offers a unique blend of natural beauty, exclusive living, and unparalleled boating amenities that make it a dream destination for water enthusiasts and nature lovers alike.

Upper Captiva is renowned for its pristine beaches, lush landscapes, and vibrant wildlife, providing a serene escape from the hustle and bustle of everyday life. As you explore this idyllic island, you'll discover a variety of stunning homes designed to embrace the coastal lifestyle. Many of these properties come equipped with exceptional boating amenities, allowing you to easily access the shimmering waters of the Gulf of Mexico.

Imagine waking up to breathtaking sunrises and the gentle sound of waves lapping against the shore. With direct access to the water, your days can be filled with sailing, fishing, or simply cruising along the coastline, all from the comfort of your own backyard. The community fosters a welcoming atmosphere, where neighbors become friends, and the spirit of island living thrives.

Whether you're seeking a vacation getaway, a year-round residence, or an investment opportunity, Upper Captiva offers a diverse selection of homes that cater to your desires. From charming beach cottages to luxurious waterfront estates, there's a perfect slice of paradise waiting for you.

Come experience the magic of Upper Captiva, where boating adventures and tranquil living intertwine to create an extraordinary lifestyle. Your dream home awaits in this coastal haven!

Newest Upper Captiva Homes with Boating Amenities

$1,225,000
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
$849,000
2 Beds ⋅ 3 Baths ⋅ 2026012142 MLS ⋅ Upper Captiva BLDG.
Island Living with Room to Expand – A Rare North Captiva Opportunity Welcome to 201 White Pelican Way, a unique island retreat located on North Captiva, a private boat-access-only barrier island just off the coast of Southwest Florida. Known for its pristine beaches, turquoise Gulf waters, abundant wildlife, and peaceful golf-cart-only lifestyle, North Captiva offers a level of tranquility that’s becoming harder to find. This elevated island home features a 1-bedroom, 2-bath main residence plus a den with potential to convert into a second bedroom, offering flexible space for guests or additional sleeping quarters. The property also includes a separate ground-level 1-bedroom, 1-bath apartment, ideal for visitors, extended family, or generating rental income. Designed to embrace the outdoors, the home features multiple levels of decking and sitting areas, creating inviting spaces to relax, entertain, and take in partial Gulf views and coastal breezes. Whether enjoying your morning coffee at sunrise or watching the stars come alive at night, the outdoor living spaces capture the true essence of island life. The property also includes several storage buildings, perfect for golf carts, beach gear, fishing equipment, and island essentials. Adding even more value, the sale includes the adjoining lot behind the home, opening the door to exciting possibilities. Create a large private pool and outdoor living oasis, expand the existing property, or build a second home for guests or additional rental potential. North Captiva is a destination where dolphins play offshore, pelicans glide overhead, and the night sky is filled with stars. Accessible only by boat or ferry and navigated by golf cart, the island offers a laid-back lifestyle surrounded by beautiful beaches, incredible fishing, and protected natural preserves. Whether you're looking for a private island getaway, a full-time retreat, or an investment property with strong vacation rental appeal, this property offers a rare opportunity to own a true piece of North Captiva paradise.

201 White Pelican Dr, Captiva
$150,000
225056927 MLS ⋅ Upper Captiva BLDG.
Build Your Private Island Dream Home --- Escape to paradise on exclusive Upper Captiva Island, where this remarkable piece of land offers the best of both worlds—beach and bay access. Nestled between the pristine shoreline of the Gulf of Mexico and the tranquil waters of Foster’s Bay, this lot is the ideal canvas for your dream island retreat. Surrounded by lush tropical foliage and located in a peaceful, car-free community, this property offers ultimate privacy and a true sense of seclusion. Whether you're seeking a luxurious second home or a one-of-a-kind vacation getaway, you’ll enjoy the rare combination of direct beach access for sun-soaked days and convenient bay access for paddleboarding, kayaking, and boating adventures. With no cars, no crowds, and unmatched natural beauty, Upper Captiva is a hidden gem where time slows down. This is your opportunity to create a custom island home in one of Florida’s most remote and magical settings. More pictures will be available at a later date

Captiva
$3,499,000
225027495 MLS ⋅ Upper Captiva BLDG.
HEAVEN ON EARTH! An exceptional and rare opportunity to own an almost full acre of beachfront property with bay to gulf access on North Captiva Island with access via boat, ferry, airplane or helicopter. One of a kind property located in pure paradise with white sandy beaches, endless million dollar sunset views and engineered plans for a gorgeous new home are also available to view. This is a golf cart only island with access to some of the best fishing, nature walks, water recreation activities on five miles of sandy beaches - you can walk or ride your beach bike all the way to Red Fish Pass with incredible shelling, beaches and waters. Lots of activities available - swim at Mangos and enjoy cocktails or relax - Barnacles offers great food, outdoor games and Over the Waterfront Restaurant is a quaint place to enjoy a great lunch or dinner. The North Captiva Island Club and Safety Harbor offers memberships for tennis/pickleball/swimming and more. Live your best life in a wonderful oasis - laid back lifestyle - located within minutes by water to Useppa Island, just south of Cayo Costa, Cabbage Key and a vibrant nature wonderland with daily sightings of dolphins, manatees, birds and more. Build the plans Seller has or create your own dream home. Only three hundred homes, more than half of the Island is a State Park. Minutes away is Pine Island which offers a ferry transport out to the island every two hours during the day! This is your time, your moment to grab a priceless piece of property and live your best life!

4281 Point House Trl, Upper Captiva
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