Windward Cay Homes for Sale

About Windward Cay Neighborhood

Windward Cay sits at the southern edge of Winter Garden's 34787 ZIP, on a stretch of Tilden Road that has become one of West Orange County's most desirable residential corridors. The single gated entrance opens directly across Tilden Road from another gated community, Wintermere Pointe, and the two communities effectively bookend that intersection. Inside the gates, Rockrose Drive loops through the neighborhood, with homes either backing up to a wooded conservation area on the south and west or fronting one of the community's interior ponds.

The community was developed quickly — the first homes broke ground in 2002 and the buildout was largely complete by 2004, which means every home benefits from Florida's post-2002 hurricane-era building code updates. Floor plans range from roughly 2,300 to 3,800 square feet, with three to five bedrooms, two to four bathrooms, and two- to three-car garages. Builders varied across the buildout, so exteriors and elevations differ noticeably from house to house — a contrast to many of the larger production-builder neighborhoods that came later in the corridor. More than half the homes here have private pools, and homes with conservation or pond exposure typically command a premium on the resale market.

What makes Windward Cay distinctive is what it doesn't have. There's no community pool, no clubhouse, no fitness center, no playground — just a gated entrance, sidewalks, common-area landscaping, and the perimeter conservation buffer. That deliberate minimalism keeps HOA dues comparatively modest for a gated 34787 community, which has historically appealed to buyers who want a private, secured address near the Horizon West / Windermere amenity belt without paying the carrying cost of a resort-amenity community. The Shoppes at Windward Cay — the small commercial plaza with a Walgreens, a few restaurants, and a handful of service businesses — sits at the corner of Tilden Road and Winter Garden Vineland Road, roughly half a mile from the gate.

Windward Cay Location & Connections

Windward Cay's address — Tilden Road, just west of Winter Garden Vineland Road (SR-535) — places it at a deliberately convenient pivot point inside Winter Garden. From the gated entrance, residents are roughly 0.7 miles south of SR 429 (the Daniel Webster Western Beltway) and a few minutes east of Florida's Turnpike — the two highways that together carry most of West Orange County's commuter traffic. The result is fast access in three directions: north toward Winter Garden's historic downtown, south toward Disney and the Horizon West villages, and east toward downtown Orlando without ever needing to enter the Tilden Road / SR-535 backups during peak retail hours.

The immediate surroundings are a mix of similar-vintage gated subdivisions, newer M/I Homes builds farther west on Tilden Road, and the commercial corner at Tilden and Winter Garden Vineland Road anchored by the Shoppes at Windward Cay. The southern side of the community fronts conservation land, which insulates the neighborhood from any future high-density development along that flank.

Windward Cay Amenities & Lifestyle

Windward Cay is deliberately a low-amenity neighborhood — the value proposition has always been "gated, secure, well-built, and quiet," not "resort lifestyle on-site." Residents lean on the dense amenity belt around the intersection of Tilden Road and Winter Garden Vineland Road for parks, shopping, dining, and recreation. Winter Garden's historic downtown is roughly 10 minutes north; the Horizon West villages start a few minutes south.

How Windward Cay Compares

Windward Cay's pitch is unusual for the Tilden Road / Winter Garden Vineland Road corridor: a small, gated, mature-buildout neighborhood without resort amenities, surrounded by significantly larger and newer master-planned communities that carry higher HOA dues and, in many cases, CDD assessments on top. The comparison below frames the value choice buyers are making.

Windward Cay HOA & CDD Information

Windward Cay is governed by a homeowners association responsible for maintaining the gated entrance, common-area landscaping, perimeter conservation buffer, and street-level community appearance. Because the community deliberately omits a pool, clubhouse, fitness center, and other resort-style facilities, HOA dues here have historically been lower than at comparable gated communities along Tilden Road and Winter Garden Vineland Road. Architectural standards apply to exterior modifications, paint colors, fencing, and landscaping changes.

CDD (Community Development District) status should be verified against Orange County records before purchase. Many of the newer master-planned communities in this corridor carry CDD assessments in addition to HOA dues; Windward Cay's status as a 2002 – 2004 buildout means it may or may not have a CDD layer attached.

Frequently Asked Questions