Windward Cay Homes with Gated Community features

Welcome to Windward Cay, a hidden gem in the heart of Naples, Florida, nestled within the picturesque Collier County. This charming subdivision offers a unique blend of tranquility and luxury, making it an ideal destination for families, retirees, and anyone looking to enjoy the quintessential Florida lifestyle.

Windward Cay is a gated community, providing residents with a sense of security and exclusivity. As you enter through the elegant gates, you’ll be greeted by beautifully landscaped grounds and a warm, welcoming atmosphere. The neighborhood boasts a variety of stunning homes, each thoughtfully designed to enhance comfort and style. From spacious single-family residences to cozy villas, there is a perfect home for everyone in this vibrant community.

One of the standout features of Windward Cay is its proximity to Naples’ world-renowned beaches, upscale shopping, and fine dining. Residents enjoy easy access to the pristine shores of the Gulf of Mexico, where sun-soaked days and breathtaking sunsets await. For those who love the outdoors, nearby parks and nature preserves offer endless opportunities for hiking, biking, and exploring Florida’s natural beauty.

In addition to its prime location and beautiful homes, Windward Cay fosters a strong sense of community. Neighbors come together for social events and activities, creating lasting friendships and cherished memories. Whether you’re relaxing by the community pool, enjoying a leisurely stroll through the neighborhood, or participating in local events, Windward Cay offers a lifestyle that is both enriching and fulfilling.

Discover the charm and elegance of Windward Cay—where your dream home awaits in the heart of Naples!

Newest Windward Cay Homes with Gated Community features

$1,375,000

3 Beds ⋅ 3 Baths ⋅ Windward Cay SubDv.

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 Drive Unit 622, Naples

$425,000

3 Beds ⋅ 2 Baths ⋅ Windward Cay SubDv.

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 Drive Unit 612, Naples

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