Waterstone Homes for Sale

About Waterstone Neighborhood

Waterstone occupies a quiet enclave in the southwest section of Windermere, with its main entrance off Winter Garden Vineland Road just west of Chase Road. The community was master-planned around European provincial architecture and developed primarily between 2010 and 2019, with home counts and final phases extending into more recent years.

The community contains approximately 120 single-family estate homes built by a roster of regional luxury builders including Brerhill Homes, David Weekley Homes, Sillman Homes, and Toll Brothers. Mediterranean and European provincial styling defines the streetscape, with barrel tile roofs, brick paver driveways, stucco exteriors, and arched entries. Homes typically range from approximately 2,700 square feet to over 9,000 square feet, with four to seven bedrooms and the majority featuring private screened pools.

Waterstone's most distinctive feature is its location directly adjacent to Windermere Preparatory School, one of Central Florida's most prominent independent schools. The community's address — within walking distance of campus — makes it a frequent choice for families with students enrolled there. The 24-hour manned guard gate, cobblestone bridge entry, landscaped common areas, and natural wetland preserve frame what is otherwise a relatively compact neighborhood footprint.

While Waterstone sits in the broader area near the southern Butler Chain of Lakes corridor, the community itself is not a Butler Chain waterfront subdivision. A small subset of homes on the western edge has lake-adjacent siting, but the majority of Waterstone homes are interior-lot estates rather than lakefront properties.

Waterstone Location & Connections

Waterstone is positioned in the southwest portion of Windermere's 34786 ZIP code, with its main entrance fronting Winter Garden Vineland Road (CR 535) just west of Chase Road. The community shares the corridor that includes Glenmuir, Sawyer Sound, Bellaria, Providence, and the Cornerstone at Summerport shopping district, placing daily errands, the Orlando Health Medical Pavilion Summerport, and the 429 Expressway within a short drive.

Downtown Windermere and Town Square sit roughly three miles north of the main gate. The southern reach of the Butler Chain of Lakes — anchored by Lake Butler — lies west of the community, although Waterstone itself is not a Butler Chain subdivision.

Waterstone Amenities & Lifestyle

Waterstone offers a quiet, gate-secured residential rhythm anchored by its proximity to Windermere Preparatory School and the southwest Windermere retail and medical corridor along CR 535. Residents tend to use the community for what it does well — privacy, security, low-traffic streets, and walkable access to Windermere Prep — while drawing on the broader Windermere area for shopping, dining, parks, and lake recreation.

How Waterstone Compares

Waterstone occupies a specific niche in the southwest Windermere luxury market: 2010s-and-newer Mediterranean estate homes behind a 24-hour guard gate, adjacent to Windermere Prep, but not on the Butler Chain. The closest direct comparisons are other guard-gated Windermere 34786 estate communities of similar vintage in the same southwest corridor.

Waterstone HOA & CDD Information

Waterstone is governed by a mandatory homeowners association that funds the 24-hour manned gate, common-area landscaping, entry features, and shared infrastructure. Specific fee amounts, payment schedules, and management company details change periodically.

To the best information available in current FNR community data, Waterstone is not subject to a Community Development District (CDD) assessment, which differentiates it from many of the newer Horizon West master-planned communities to the south.

Frequently Asked Questions