Windsor Hill Homes for Sale

About Windsor Hill Neighborhood

Windsor Hill sits in the northeast quadrant of Windermere, accessed via Windy Ridge Road off Apopka-Vineland Road. The neighborhood was developed across roughly two decades — most homes were built between 1989 and 2009 by a mix of regional luxury and custom builders, with a handful of newer infill builds completed since. The result is architectural variety rather than a single cohesive look: one home may read traditional Floridian brick, the next contemporary Mediterranean, the next a transitional spec from the late 2000s.

The defining physical feature is lot size. Half-acre to one-acre parcels are the norm here — well above the typical Windermere subdivision and well above anything new construction in the area can deliver. That space, combined with a long-established mature tree canopy, gives Windsor Hill a quiet, settled character that newer luxury communities take decades to develop. Homes range broadly in size, from roughly 2,400 square feet up to estate residences exceeding 9,000 square feet, and most include private pools.

The community offers a small interior amenity area with a tennis court and a playground beneath mature shade trees — modest by the standards of resort-style HOAs but appropriate to the neighborhood's intimate scale. There are no Community Development District (CDD) fees. The downtown Windermere Town Square is roughly one mile from the main entrance, and The Grove at Isleworth shopping and dining center sits a short drive south on Conroy-Windermere Road.

Windsor Hill Location & Connections

Windsor Hill is positioned in northeast Windermere off Windy Ridge Road, accessed from Apopka-Vineland Road. The neighborhood sits within the broader Lake Down corridor — the Butler Chain of Lakes lies to the west — and benefits from quick connections in three directions: south on Apopka-Vineland to Conroy-Windermere Road for the I-4 commute, west across Windy Ridge to downtown Windermere Town Square (about a mile), and east via Conroy-Windermere toward MetroWest, Mall at Millenia, and the SR 408 commute corridor.

Major regional connectors — Florida's Turnpike, I-4, and the SR 429 Western Beltway — are reachable within 10–15 minutes, making Windsor Hill workable for commuters to downtown Orlando, the airport, the Disney corridor, and the Lake Mary / I-4 north employment centers.

Windsor Hill Amenities & Lifestyle

Windsor Hill's lifestyle leans quiet and residential — this is not a resort-amenity community and was not built to that template. Homeowners here are buying privacy, lot size, and a Windermere 34786 address rather than clubhouse social calendars. The interior amenity area (a tennis court and playground beneath shade trees) functions more as a neighborhood gathering spot than a destination, which is consistent with how 1989–2009 custom-home subdivisions in this part of Windermere were originally laid out.

The trade-off is that residents lean on the surrounding Windermere infrastructure for shopping, dining, recreation, and services — which, given proximity to downtown Town Square, The Grove at Isleworth, and the broader Conroy-Windermere corridor, is a feature rather than a constraint.

How Windsor Hill Compares

Windsor Hill's value proposition is structural: the lot sizes and mature canopy you get here are not replicable in new construction at any reasonable price point in Windermere. Buyers comparing it to newer luxury communities are weighing established space and intimacy against amenity packages and contemporary floor plans.

Windsor Hill HOA & CDD Information

Windsor Hill operates under a homeowners association that maintains common areas, the interior park, the tennis court, and playground, along with neighborhood signage and entry features. As an established 1989-era community, the HOA structure is mature and the fee scale reflects that — generally lower-overhead than newer resort-amenity communities, but exact current figures change and should be verified before purchase.

Windsor Hill does not have CDD fees. CDD fees are a financing mechanism used by many newer Windermere/Horizon West communities to fund infrastructure, and their absence here is a meaningful annual cost difference compared to newer alternatives. Learn more about what an HOA is and what a CDD is.

Frequently Asked Questions