Windward Cay Homes with Boating Community Type

Welcome to Windward Cay, a hidden gem nestled in the picturesque city of Naples, Florida. This charming subdivision, located in Collier County, offers a serene boating community experience that is simply unmatched. Windward Cay is perfect for those who seek a lifestyle where relaxation meets adventure, surrounded by the natural beauty of Southwest Florida.

As you meander through the beautifully landscaped streets of Windward Cay, you’ll find a collection of stunning homes that cater to a variety of tastes and preferences. Each residence is designed with comfort and functionality in mind, featuring spacious layouts, modern amenities, and often, breathtaking views of the serene waterways that define this community.

What truly sets Windward Cay apart is its direct access to some of the best boating opportunities in the region. Imagine stepping out of your backyard and onto your boat, ready to explore the pristine waters of the Gulf of Mexico or simply enjoy a sunset cruise along the coast. With a variety of boat docks available, residents can easily embrace the nautical lifestyle and create lasting memories on the water.

In addition to its boating allure, Windward Cay is conveniently located near Naples’ vibrant dining, shopping, and entertainment options. Whether you're indulging in fresh seafood at a local restaurant or exploring the charming boutiques, you’ll find everything you need just moments away.

Windward Cay is more than just a neighborhood; it’s a lifestyle choice that invites you to enjoy the best of Florida living. Come experience the magic of this boating community – your dream home awaits!

Newest Windward Cay Homes with Boating Community Type

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windward Cay BLDG.

Skip Windstar's 7-year golf waitlist — full golf membership transfers at closing. Windstar on Naples Bay caps golf membership at 350. The waitlist currently runs approximately seven years. This sale is the shortcut: seller relinquishes their full golf membership at closing, giving the buyer immediate access to the Tom Fazio championship course, clubhouse, and practice facility — no waitlist (initiation fee and dues apply). The home: fully furnished 3BR/3BA two-story townhouse with den and 1-car garage, directly on the golf course inside Windstar's private gates — Naples' only gated golf community with direct bay access, a private marina, and its own beach on Keewaydin Island. The water: deeded Boat Slip #13 at Southpointe Yacht Club — deep-water marina fully rebuilt in 2023 with new pilings and composite docks. Direct Naples Bay and Gulf access, no bridges. Slip ownership includes private marina pool/spa and common area. Golf in the morning. Gulf by afternoon. Home on the course. One closing delivers all three. Furnished. Move-in ready.

4700 Yacht Harbor DR Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ Windward Cay BLDG.

Discover exceptional value and an unbeatable lifestyle in this beautifully maintained first-floor residence located in the prestigious gated community of Windstar on Naples Bay. Offering nearly 1,800 square feet of thoughtfully designed living space, this 2-bedroom, 2-bathroom condo with a den features soaring vaulted ceilings, crown molding, plantation shutters, and an attached one-car garage. Perfectly positioned just steps from the community pool, the screened lanai overlooks lush tropical landscaping and the picturesque 7th tee, creating a peaceful backdrop that perfectly complements the community's renowned golf lifestyle. A fully paid reverse osmosis water treatment system provides an added level of comfort and value. Windstar is one of Naples' most exclusive communities, offering a rare combination of championship golf and direct Gulf access. Residents enjoy a private boat shuttle to Keewaydin Island, a 72-slip deep-water marina, and a beautifully redesigned clubhouse with waterfront dining overlooking Naples Bay. The community also features tennis, bocce, a state-of-the-art fitness center, and a vibrant social calendar, with residents receiving priority on the waitlist for Social and Social Summer Golf Memberships. Ideally located just minutes from the vibrant Bayshore Arts District, Naples Botanical Garden, and less than four miles from the world-class dining, shopping, and white sand beaches of 5th Avenue South, this home offers the perfect opportunity for full-time living, a seasonal retreat, or an exceptional investment in one of Naples' most desirable waterfront communities.

4700 Yacht Harbor DR Unit 612, Naples

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