Explore Homes for Sale in Windward Cay, Naples, FL
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Windward Cay, Naples, FL Homes for Sale: Your Guide with Broker Brothers

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Discover an exquisite selection of Windward Cay, Naples, FL homes for sale, offering an idyllic Southwest Florida lifestyle. Nestled within a coveted Naples location, Windward Cay presents a charming collection of single-family residences, many boasting serene lake views and lush tropical landscaping. This peaceful community provides residents with convenient access to pristine Vanderbilt Beach, upscale shopping at Mercato, and a diverse array of fine dining experiences. Prospective buyers seeking properties in a well-established, tranquil neighborhood will find exceptional opportunities among the current listings for homes for sale in Windward Cay, ideal for both year-round living and seasonal retreats. Explore the unique appeal of this distinguished Naples enclave.

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Exploring Windward Cay Real Estate Opportunities

As you begin your search for Windward Cay, Naples, FL homes for sale, you'll uncover a community celebrated for its tranquil ambiance and prime location. This desirable neighborhood, renowned for its beautifully maintained properties, offers residents a serene escape while remaining just moments from Naples' most vibrant attractions. The focus here is on comfortable, luxurious living, making it a highly sought-after destination for those looking to purchase a home.

The Allure of Windward Cay's Location

Positioned conveniently within Naples, Windward Cay provides unparalleled access to a wealth of amenities. Residents frequently enjoy short drives to the sugar-sand shores of Vanderbilt Beach and Delnor-Wiggins Pass State Park, perfect for sunbathing, shelling, and watching the sunset. Furthermore, the upscale shopping and dining at Mercato and Waterside Shops are mere minutes away, ensuring a sophisticated lifestyle is always within reach. Exploring the local area reveals a blend of natural beauty and urban convenience.

Diverse Homes for Sale in Windward Cay

The selection of Windward Cay homes for sale typically encompasses spacious single-family residences designed to cater to a variety of preferences and needs. Many of these properties feature open-concept floor plans, private swimming pools, and expansive lanais, ideal for embracing Florida's outdoor living. You'll often find homes with picturesque lakefront views, adding to the community's serene charm.

Architectural Styles and Features

Prospective buyers exploring properties in Windward Cay will encounter a range of architectural styles, from elegant Mediterranean-inspired designs to more contemporary aesthetics. These homes frequently include high ceilings, gourmet kitchens, luxurious master suites, and meticulously landscaped yards. When considering homes for sale, pay attention to unique details such as custom cabinetry, upgraded appliances, and smart home technology that enhance modern living. Many residences are also designed to maximize natural light, creating bright and inviting interiors.

Embracing the Windward Cay Lifestyle

Living in Windward Cay means embracing a lifestyle characterized by leisure, convenience, and community. The neighborhood’s quiet streets and friendly atmosphere make it an ideal setting for families, retirees, and individuals alike. The opportunities for recreation are boundless, extending beyond the community's borders.

Recreation and Nearby Attractions

Beyond the immediate comforts of their homes, residents of Windward Cay enjoy proximity to numerous recreational facilities. Nearby, championship golf courses abound, catering to enthusiasts of all skill levels. Additionally, the cultural offerings of Artis—Naples and the vibrant Fifth Avenue South are easily accessible, providing world-class entertainment and dining. For those seeking active pursuits, numerous parks and nature preserves offer trails for walking, jogging, and biking, making Windward Cay an excellent choice for a dynamic Florida lifestyle.

Navigating Your Search for Windward Cay Homes

When you're ready to explore the exciting inventory of Windward Cay, Naples, FL homes for sale, partnering with a knowledgeable local expert is invaluable. Understanding the nuances of this specific market, including property values, community regulations, and upcoming listings, can significantly streamline your home-buying process. Broker Brothers is dedicated to providing comprehensive insights and personalized service, ensuring a seamless experience as you find your perfect home in this exquisite Naples community.

Newest Homes for Sale in Windward Cay, Naples, FL

4600 Yacht Harbor Dr Unit 412, Naples
$1,099,000
2 Beds ⋅ 2 Baths ⋅ 226037973 MLS ⋅ Windstar BLDG.
Welcome to 4600 Yacht Harbor Drive in Windward Cay at Windstar on Naples Bay, one of Naples’ most desirable gated waterfront communities. This beautifully renovated, furnished end-unit residence offers 2 bedrooms plus a den, 2 full bathrooms, and approximately 2,185 square feet of inviting living space with tranquil golf course views. Rich hardwood flooring, solid-core doors, crown molding, plantation shutters, custom lighting, and thoughtfully selected finishes create a warm, refined interior. The expansive chef’s kitchen features custom cabinetry, granite countertops, a beautiful backsplash, an induction cooktop, a pot filler, and generous storage, making it equally suited to everyday living and entertaining. The spacious primary suite provides a peaceful retreat with custom closet built-ins and a beautifully appointed bathroom. Additional highlights include a formal dining room, a versatile den ideal for a home office or additional guest space, custom window treatments, a stackable washer and dryer, and an approximately 8-by-6-foot storage room. Overlooking Windstar’s picturesque 8th fairway, the residence enjoys a serene backdrop of lush tropical landscaping and beautifully maintained greens. Windward Cay residents enjoy a heated community pool, grilling area, elevator access, and an intimate residential setting. Windstar on Naples Bay offers an exceptional collection of amenities, including a Tom Fazio-designed 18-hole golf course, driving range, and a newly renovated clubhouse with spectacular Naples Bay views. The brand-new, recently completed fitness center adds another highlight to the community’s active lifestyle, complementing its tennis courts and bocce facilities. A full-service deep-water marina with direct Gulf access enhances the waterfront experience, while a seasonal boat shuttle to Windstar’s private beach on Keewaydin Island offers a secluded Gulf-front escape. Golf and clubhouse memberships are available separately, subject to availability and club requirements. Ideally located just minutes from downtown Naples, Fifth Avenue South, Third Street South, acclaimed dining, shopping, and Gulf beaches, Windstar also offers convenient access to the Bayshore Arts District, Naples Botanical Garden, and Naples Pickleball Center. For buyers considering The Moorings, Park Shore, or Gulf Shore Boulevard, Windstar presents a compelling opportunity to enjoy a gated waterfront community with exceptional amenities, natural beauty, and proximity to everything Naples has to offer. Discover beautifully renovated interiors, peaceful golf course views, and the best of the Southwest Florida lifestyle. One or more photos have been virtually staged, AI-generated, or rendered.

4600 Yacht Harbor Dr Unit 412, Naples
4650 Yacht Harbor Dr Unit 124, Naples
$649,000
2 Beds ⋅ 2 Baths ⋅ 226038417 MLS ⋅ Windstar BLDG.
Golf Course Views and Private Beach Access on Naples Bay! Welcome to this completely updated, second-floor gem in the prestigious Windstar on Naples Bay community. Offering 1,589 square feet of thoughtfully curated living space, this move-in ready 2-bedroom-plus-den features a new custom-built Murphy bed that seamlessly transforms the space  into an immediate third guest suite. This residence has been beautifully modernized throughout and delivers the ultimate Southwest Florida lifestyle with absolutely zero post-closing work required. Start your day with coffee on your private lanai overlooking the pristine greens on the 7th hole, relax by the expansive community pool, or embark on a waterfront adventure aboard Windstar's private shuttle boat, the Keewaydin Queen, which takes residents directly to a private island beach. Ideally located just 10 minutes from downtown Naples and historic Olde Naples, you will enjoy effortless daily access to world-renowned dining, luxury shopping, entertainment, and the distinct charm of Fifth Avenue South. Whether you are seeking a full-time residence, an effortless seasonal retreat, or a prime investment opportunity, this condo offers an exceptional blend of modern updates, flexible living space, scenic golf views, and stunning daily sunsets. Experience championship golf along the bay, boating adventures, and exclusive beach access all in one remarkable, highly sought-after Naples community.

4650 Yacht Harbor Dr Unit 124, Naples
4700 Yacht Harbor Dr Unit 622, Naples
$1,375,000
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
4700 Yacht Harbor Dr Unit 612, Naples
$425,000
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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