Windward Cay Homes with Sidewalk Amenities

Welcome to Windward Cay, a picturesque subdivision nestled in the heart of Naples, Florida, within the beautiful Collier County. Known for its serene atmosphere and vibrant community spirit, Windward Cay offers a perfect blend of comfort and convenience, making it an ideal place to call home.

As you explore this charming neighborhood, you’ll find a variety of well-appointed homes, each designed with modern living in mind. Many properties boast spacious layouts, lush landscaping, and inviting outdoor spaces that are perfect for family gatherings or quiet evenings under the stars. The homes in Windward Cay are enhanced by the presence of sidewalks, promoting an active lifestyle and encouraging residents to enjoy leisurely strolls, morning jogs, or evening bike rides throughout the community.

One of the standout features of Windward Cay is its commitment to creating a welcoming environment. The subdivision is designed with pedestrian-friendly amenities, allowing residents to easily access nearby parks, schools, and shopping centers. The lush greenery and well-maintained sidewalks not only enhance the aesthetic appeal of the area but also foster a sense of community among neighbors.

Living in Windward Cay means embracing the Naples lifestyle, where sunny days and warm evenings invite you to explore the beautiful beaches, indulge in world-class dining, and partake in a variety of recreational activities. Whether you’re a growing family, a retiree, or anyone in between, Windward Cay is a community that offers the perfect backdrop for your next chapter. Come discover the charm of Windward Cay and experience the best of Naples living!

Newest Windward Cay Homes with Sidewalk Amenities

$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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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.