Wintermere Pointe Homes for Sale

About Wintermere Pointe Neighborhood

Wintermere Pointe occupies a single, defined parcel at the intersection of Tilden Road and Winter Garden Vineland Road (CR 535) — the same road that runs south into Windermere and forms the spine of the Windermere / Winter Garden border corridor. The community was carved out of former orange groves in two phases, with the first homes delivered in 1999 and the final phase wrapping in 2004. Cambridge Homes (later absorbed into Standard Pacific/CalAtlantic and ultimately Lennar) was the sole builder, which gives the neighborhood a more consistent architectural vocabulary than the multi-builder communities that came online after it.

The community is fully gated, with a single palm-lined entry off Tilden Road that faces the gated entry of the Windward Cay community directly across the street. Inside the gate, Wintermere Pointe Drive forms the primary loop, with two internal ponds, two conservation/wetland preserves, and a central recreation area anchored by a tennis court and a children's playground. There is no clubhouse, pool, or fitness center — the community trades resort-style amenities for lower HOA cost and larger homesites than newer comparable developments offer.

Homes range from approximately 2,000 to over 4,200 square feet, with 4 to 5 bedrooms, 2 to 4 bathrooms, and 2 to 3 car garages in both one-story and two-story configurations. Roughly 29 of the 203 homes sit on the two interior ponds; another tranche backs to the conservation easements, and the remainder are interior homesites. The architectural style is consistent Florida traditional — tile roofs, stucco exteriors, screened lanais standard, and a meaningful share of homes built with or later upgraded to private pools.

Wintermere Pointe is often grouped in casual conversation with the neighboring Wintermere Harbor community immediately to the east, but the two are distinct subdivisions with separate HOAs and different character — Wintermere Harbor is a smaller, lake-oriented community on Lake Whitney; Wintermere Pointe is a larger inland community whose primary water features are internal ponds and conservation views rather than named-lake frontage.

Wintermere Pointe Location & Connections

Wintermere Pointe sits at one of the more strategically positioned intersections in southwest Winter Garden. The community fronts Tilden Road on the south and Winter Garden Vineland Road (CR 535) on the west, with SR 429 less than a mile north and the Florida Turnpike a few miles east. The neighborhood is roughly equidistant between downtown Winter Garden and the Windermere area, which means residents can reach Plant Street, Winter Garden Village, and Windermere's Butler Chain corridor in under 10 minutes each.

Vacant land to the west of the community provides a natural buffer along Winter Garden Vineland Road, and the conservation easements inside the community absorb the perimeter on the east and north sides. Across Tilden Road sits the Shoppes at Windward Cay (a small retail strip serving the immediate area) and the Windward Cay residential community.

Wintermere Pointe Amenities & Lifestyle

Wintermere Pointe is a quiet, established residential community without the resort-style amenity package that newer developments emphasize. The trade-off is deliberate — homeowners get a gated single-entry community, generous interior conservation buffers, and lower carrying costs in exchange for a more modest internal amenity set. For active recreation, shopping, dining, golf, and entertainment, residents lean heavily on the broader Winter Garden corridor that surrounds the community.

How Wintermere Pointe Compares

The most useful comparisons for Wintermere Pointe are the two communities that sit directly across the street and next door, plus the newer construction options in the broader corridor. Buyers shopping this area typically weigh established gated communities like Wintermere Pointe against newer Horizon West villages farther south or against the lake-oriented Wintermere Harbor next door.

Wintermere Pointe HOA & CDD Information

Wintermere Pointe is governed by a homeowners association that maintains the gated entry, the tennis court and playground, the two internal ponds, the conservation area buffers, common-area landscaping, and the private street lighting along Wintermere Pointe Drive. The HOA also administers the architectural review process (ARC) and gate access — both common touchpoints for new buyers and sellers.

The community does not appear to carry Community Development District (CDD) fees, which is consistent with its late-1990s/early-2000s development era — most CDD-financed communities in this corridor came online after 2005. Buyers should verify current CDD status via Orange County Property Appraiser records.

Frequently Asked Questions