Leeward Cay Condos for Sale at Windstar Naples

Leeward Cay at Windstar

Leeward Cay occupies a distinctive position within Windstar on Naples Bay. Rather than a conventional stacked condominium development, Leeward Cay provides a low-density, ground-oriented residential format with the scale and garage space many buyers associate with a villa or single-family home.

The neighborhood includes approximately 16 residences with both attached and detached villa designs represented. Its limited scale, mature landscaping, private outdoor spaces and location near Windstar's fourth fairway create a quieter residential environment than many larger Naples condominium communities.

Villa-Style Living With Condominium Convenience

Leeward Cay can be especially attractive to buyers who want ground-oriented living, substantial interior space and attached garage parking without moving into a larger detached-home neighborhood.

Its residential format is different from a traditional multi-story condominium building. Individual properties may feel more like villas, yet ownership, association responsibilities and insurance arrangements should still be evaluated according to the current legal documents for the specific residence.

Spacious Floor Plans

Original Leeward Cay residences generally provide approximately 2,000 to 2,500 square feet of living area, making them larger than many conventional Naples condominium options.

Floor plans can provide multiple bedrooms, guest accommodations, dining areas, generous primary suites and flexible living spaces suitable for seasonal or full-time ownership.

Because the residences have been renovated independently over time, current layouts may differ from original plans. Interior walls, kitchens, bathrooms, flooring and outdoor spaces may have been substantially modified in individual properties.

Attached Two-Car Garages

Attached two-car garages are one of Leeward Cay's strongest practical advantages when compared with condominium communities that rely on carports, assigned surface parking or detached garages.

Garage space can provide room for vehicles, bicycles, golf equipment, beach gear and household storage while allowing direct access into the residence.

Buyers should verify dimensions, door condition, storm protection, storage systems, electrical improvements and any association rules affecting garage use.

Golf and Lake Views

Leeward Cay lies near the fourth fairway of Windstar's golf course. Depending upon the residence, rear views may include fairways, neighborhood lakes, tropical landscaping or combinations of these elements.

View quality should be evaluated according to rear orientation, landscaping, privacy, golf-course position, distance from active play and the relationship between the lanai or pool and the permanent setting.

Two residences of similar size can therefore provide very different ownership experiences depending upon homesite position and rear exposure.

Private Pools and the Neighborhood Pool

Leeward Cay provides a neighborhood community swimming pool and patio area, allowing owners to enjoy pool recreation without necessarily maintaining a private pool.

Select residences also include their own private swimming pools and screened outdoor-living areas. These properties should be evaluated differently because private pools add both lifestyle value and individual maintenance responsibilities.

Buyers considering a private-pool residence should review pool surface condition, equipment, heating system, screen enclosure, decking, drainage and the current association's responsibility for any exterior components.

Screened Lanais and Outdoor Living

Screened lanais and patios are central to the Leeward Cay lifestyle. Outdoor areas can extend the useful living space while providing views toward golf, water and mature landscaping.

Buyers should compare covered depth, rear exposure, privacy, afternoon sun, screen condition, flooring and storm protection. Where a residence has been reconfigured or expanded, permits and association approvals should be verified.

Renovated vs. More Original Villas

Leeward Cay residences have been updated individually, creating meaningful differences in condition and effective age.

Leeward Cay Association Due Diligence

Association review is especially important in villa-style communities because buyers may otherwise assume that ownership responsibilities mirror those of a detached home.

Windstar Golf Is Separate From Residence Ownership

Leeward Cay sits within Windstar's Tom Fazio-designed private golf environment, but Windstar is a non-bundled private-club community.

Purchasing a Leeward Cay residence does not by itself require or guarantee a particular golf membership. Golf privileges, dining, fitness, racquet amenities and other Club opportunities depend upon the applicable membership category.

Buyers interested in private-club membership should verify current availability, waiting procedures, initiation requirements, dues and privileges before making those benefits part of a purchase decision.

Naples Bay Marina and Boating

Windstar's direct relationship with Naples Bay is one of the characteristics that distinguishes it from many inland Naples golf developments.

The broader community includes marina opportunities with access toward Gordon Pass and the Gulf of Mexico. Leeward Cay ownership, however, does not automatically convey a boat slip.

Buyers interested in boating should separately verify slip availability, legal ownership or leasing arrangement, dimensions, vessel limitations, water depth, fees and transfer rights.

Private Beach Experience on Keewaydin Island

Applicable Windstar memberships may provide access to the Club's private beach experience on Keewaydin Island through a boat shuttle.

Eligibility, shuttle schedules, guest privileges and other beach-related policies should be confirmed under current Club rules rather than assumed to accompany every Leeward Cay residence.

Near the Bayshore Arts District and Downtown Naples

Leeward Cay combines the privacy of gated Windstar with convenient access to the Bayshore Arts District, Naples Botanical Garden, Celebration Park and South Naples waterfront destinations.

Fifth Avenue South, Third Street South, Downtown Naples, Gulf beaches, restaurants, galleries and shopping are also within convenient driving distance.

How to Value a Leeward Cay Residence

Leeward Cay valuation should begin with recent Leeward Cay sales whenever sufficiently comparable transactions exist. Because there are only approximately 16 residences, the transaction pool can be limited.

When broader comparison is necessary, the most useful alternatives are generally other low-density Windstar villas or coach homes with similar living area, garages, outdoor living, view and ownership responsibilities.

Use the Windstar on Naples Bay Market Report for current community-wide listings and recent sales, then narrow the analysis to properties that genuinely compete with Leeward Cay.

Selling a Leeward Cay Residence

Leeward Cay sellers should market the characteristics that make the neighborhood different from conventional Windstar condominiums: its approximately 16-residence scale, villa-style design, attached two-car garages, golf and lake views, outdoor living and private-pool opportunities.

The listing should clearly communicate whether the residence is attached or detached, its rear orientation, view, pool configuration, floor plan, significant renovations and association responsibilities.

Documentation for roof work, windows and doors, storm protection, HVAC replacement, pool renovations, electrical or plumbing work and permitted remodeling can help buyers understand the property's effective condition.

Compare Similar Windstar Villas and Coach Homes

Buyers attracted to Leeward Cay's ground-oriented design, garage space and residential feel may also want to compare other lower-density Windstar attached-home neighborhoods.

Northstar
Villas Somerset
Condos Marina Cove
Coach Homes

Explore Windstar on Naples Bay

Return to the Windstar on Naples Bay real estate guide to compare all 15 residential neighborhoods, including detached homes, villas, coach homes and condominiums.

Buyers comparing attached residences can also explore Naples luxury condos, while buyers researching private-club communities can use the Naples luxury golf communities directory.