Windward Cay Condos at Windstar on Naples Bay

Windward Cay is a 48-residence condominium neighborhood within Windstar on Naples Bay. Low-rise buildings contain conventional condominium and townhome-style configurations, with golf, preserve and landscaped outlooks varying by residence.

Its range of layouts creates different ownership experiences. A ground-floor condominium and a larger multi-level residence should be compared by their actual configuration, accessibility, view and outdoor space.

Floor Plans and Residential Scale

Documented residences range from approximately 1,800 to more than 3,000 square feet. Two- and three-bedroom designs are represented, with dens or flexible spaces in some plans.

Verify recorded living area and the current layout. Bedroom separation, kitchen arrangement, storage, ceiling height and usable outdoor space can make similarly sized homes function differently.

Ground-Floor, Upper-Level and Townhome Living

Ground-floor homes may appeal to buyers seeking easier access. Upper-level residences can offer greater privacy and elevated views, while multi-level plans provide separation between bedrooms and principal living areas.

Confirm stairs and elevator arrangements for the individual residence. Building appearance alone does not establish its accessibility or the location of everyday living spaces.

Golf, Preserve and Mangrove Views

Golf outlooks differ according to fairway, green, tee and cart-path position. Compare distance from active play, privacy and the width of the permanent view.

Preserve-oriented residences offer a different visual setting. Evaluate vegetation, neighboring buildings, rear exposure and the outlook from the living room and outdoor seating areas individually.

Lanais, Parking and Neighborhood Recreation

Screened lanais extend living outdoors. Compare covered depth, exposure, privacy, flooring, screens and storm protection. Verify permits and association approvals for material modifications or enclosures.

Parking arrangements vary and may include garages or under-building covered spaces. Confirm the precise legal interest, dimensions, storage rights, guest parking and vehicle restrictions.

Windward Cay's neighborhood pool, spa and cabana provide recreation close to home. Review current operating policies, guest rules and association responsibilities for maintenance and capital work.

Renovations and Major Systems

Compare kitchens, bathrooms and flooring alongside air conditioning, water heaters, plumbing, electrical systems, windows and doors. Verify storm protection for the specific property.

Distinguish cosmetic improvements from work addressing major systems. Documentation for permits, approvals and warranties helps establish the scope of material alterations.

Condominium Association Review

Review current budgets, reserves, master insurance, deductibles, assessments and planned capital projects. Establish responsibility for roofs, exteriors, windows, doors, parking and lanai components.

Confirm rental terms, permitted lease frequency, application requirements and pet restrictions through current written rules. Include property-specific insurance and anticipated ownership expenses in the purchase analysis.

Property-Specific Golf Membership Opportunities

Evaluate residential ownership and Club membership separately. A seller may advertise a membership opportunity associated with a particular transaction, but buyers must verify eligibility, transfer procedures, timing, initiation requirements and dues directly with the Club.

An arrangement offered with one residence should not be assumed to apply throughout Windward Cay.

Boat Slips and Windstar's Waterfront Lifestyle

An individual seller may separately own a boat slip and offer that interest alongside a residence. Confirm its legal ownership, location, dimensions, lift equipment, fees, transferability and vessel restrictions.

Condominium ownership alone does not establish marina rights. Buyers interested in Windstar's Keewaydin Island beach experience and boat transportation should also confirm current eligibility, guest privileges and operating arrangements.

Windward Cay Values and Recent Sales

Begin with comparable Windward Cay transactions, distinguishing conventional condominiums from larger multi-level plans. Account for recorded area, floor, view, exposure, lanai, parking, renovation and association obligations.

Value any verified membership or boat-slip interest separately. The Windstar Market Report provides broader activity, but community-wide averages should be narrowed before estimating an individual residence's value.

Compare Related Windstar Neighborhoods

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Somerset at Windstar Explore attached-home alternatives Yacht Harbour Cove condominiums at Windstar

Yacht Harbour Cove at Windstar Compare marina-oriented residences

Return to the Windstar on Naples Bay guide or explore other Naples golf communities.

Buying or Selling in Windward Cay

Schulz Realty LLC helps buyers and sellers compare Windward Cay residences by layout, accessibility, view, outdoor living, condition and documented ownership rights. Sellers should organize improvement records and association information so buyers can evaluate the property and its obligations together.

Contact Schulz Realty for Listings & Private Tours.

Availability, prices, living areas, amenities, maintenance responsibilities, association finances, insurance, assessments, membership terms, boating arrangements and beach privileges may change or vary. Verify material information through current listings, governing documents, association and Club records, inspections, insurance professionals and title review.

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Windward Cay Condos in Windstar

$1,375,000

3 Beds ⋅ 3 Baths ⋅ 2026023271 MLS ⋅ ACTIVE Status ⋅ 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

$1,099,000

2 Beds ⋅ 2 Baths ⋅ 226037973 MLS ⋅ ACTIVE Status ⋅ Windward Cay 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

$649,000

2 Beds ⋅ 2 Baths ⋅ 226038417 MLS ⋅ ACTIVE Status ⋅ Windward Cay 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

$425,000

3 Beds ⋅ 2 Baths ⋅ 2026028731 MLS ⋅ ACTIVE Status ⋅ 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.