Windward Cay Real Estate

Windward Cay Real Estate

Welcome to Windward Cay, a hidden gem nestled in the heart of Naples, Florida! This charming subdivision offers a unique blend of tranquility and accessibility, making it a perfect choice for families, retirees, and anyone looking to embrace the Florida lifestyle.

Windward Cay is characterized by its beautifully landscaped streets, lined with lush palm trees and vibrant gardens. The community features a mix of single-family homes and townhouses, each exuding a distinct character and charm. With a variety of architectural styles, there’s something for everyone, whether you prefer a cozy cottage or a spacious family home. Many properties boast private pools, expansive patios, and stunning views of the surrounding natural beauty, providing the ideal backdrop for relaxation and entertaining.

One of the standout features of Windward Cay is its prime location. Just minutes away from the pristine beaches of Naples, residents can easily enjoy sun-soaked days along the Gulf of Mexico. The subdivision is also conveniently located near a variety of shopping, dining, and entertainment options, including the upscale boutiques and restaurants of Fifth Avenue South and the bustling Waterside Shops.

For those who appreciate outdoor activities, Windward Cay is surrounded by lush parks, golf courses, and nature preserves, offering endless opportunities for hiking, biking, and birdwatching. Additionally, the community fosters a friendly atmosphere, with neighborhood events and gatherings that encourage connections among residents.

Discover the enchanting lifestyle that awaits you in Windward Cay, where charm meets convenience in one of Florida’s most desirable locations. Come and experience the magic of Naples!

Newest Listings in Windward Cay

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ Windstar 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

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ Windstar 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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