Windward Cay Homes with Gated Community Type

Welcome to Windward Cay, a picturesque gated community nestled in the heart of Naples, Florida, within the serene Collier County. This enchanting neighborhood is the epitome of luxury living, where modern elegance meets the natural beauty of Southwest Florida.

Windward Cay boasts a stunning array of homes that cater to diverse lifestyles, making it an ideal choice for families, retirees, and seasonal residents alike. Each residence is thoughtfully designed, featuring spacious floor plans, high-end finishes, and private outdoor spaces perfect for enjoying the year-round sunshine. The community’s lush landscaping and tranquil lakes create a serene backdrop that invites relaxation and outdoor enjoyment.

As a gated community, Windward Cay offers an added layer of security and privacy, allowing residents to feel at ease in their surroundings. The well-maintained amenities include inviting walking paths, recreational areas, and a community clubhouse where neighbors can gather for social events and activities.

Located just minutes from the pristine beaches of Naples, world-class dining, and upscale shopping, Windward Cay provides the perfect balance of tranquility and convenience. Explore the vibrant local culture, indulge in gourmet cuisine, or spend your days lounging on the sun-kissed sands of the Gulf Coast.

Experience the charm and sophistication of Windward Cay, where every day feels like a vacation in paradise. Discover your dream home in this exquisite community, and embrace the luxurious lifestyle that awaits you in beautiful Naples, Florida.

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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