Windward Cay Homes with Gated Community Type

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This enchanting gated community offers a harmonious blend of luxury, comfort, and security, making it an ideal haven for families, retirees, and anyone looking to enjoy the serene lifestyle that Naples is renowned for.

Windward Cay boasts an array of beautifully designed homes, each exuding charm and modern elegance. The thoughtfully crafted residences feature spacious floor plans, high-end finishes, and lush landscaping that complements the stunning Florida sunshine. Whether you are seeking a cozy retreat or a grand family home, Windward Cay has something to suit every taste and lifestyle.

As a gated community, Windward Cay ensures peace of mind with 24/7 security, allowing residents to enjoy their surroundings without worry. The community fosters a friendly atmosphere, where neighbors become friends and shared memories are created. Enjoy leisurely strolls through the tree-lined streets, or take advantage of the nearby parks and recreational facilities that Naples has to offer.

Located just a short drive from Naples’ pristine beaches, vibrant shopping districts, and delectable dining options, Windward Cay provides the perfect balance of tranquility and convenience. Embrace the Florida lifestyle with access to world-class golf courses, nature preserves, and cultural attractions right at your doorstep.

Discover the charm of Windward Cay, where your dream home awaits in one of Florida's most sought-after communities. Experience the perfect blend of luxury living and a welcoming community—come and see for yourself what makes Windward Cay truly special!

Newest Windward Cay Homes with Gated Community Type

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS

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 ⋅ 2026028731 MLS

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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