Estates at Windermere Homes for Sale

About Estates at Windermere Neighborhood

Estates at Windermere occupies a roughly 50-acre parcel at McKinnon Road and Winder Bay Boulevard, north of Lake Butler Boulevard, in the northwest section of Windermere. The neighborhood was established in 1995, with the bulk of construction handled by Park Square Homes between 1997 and 2002. Today the community contains exactly 66 single-family estate homes laid out along Ridgewind Way, Coral Stone Court, and Winder Bay Boulevard, with a single 24-hour gated entrance and tree-lined interior streets that loop around several acres of preserved conservation and ponds.

Park Square's development model here was a custom-feel build-out across multiple architectural styles rather than a single template — the inventory includes traditional, contemporary, French Provençal, craftsman, and classic Florida designs. Square footages run from approximately 2,500 to over 5,100 under air, with 4 to 6 bedrooms, attached two- and three-car garages, and the majority of properties featuring private screened pools. Homesites are unusually generous for Central Florida: half-acre to one full acre, with mature live oaks providing the kind of canopy that newer Windermere subdivisions cannot replicate without decades of growth.

Beyond the homes themselves, residents share a small community park with a playground, tennis court, and multipurpose field. The neighborhood is non-CDD, which materially reduces long-term ownership cost compared to Horizon West and Lakes-of-Windermere-corridor communities that carry CDD assessments alongside HOA dues. Pond-front and conservation-view lots make up a meaningful share of the 66 sites, which historically supported strong resale values relative to the broader 34786 market.

Estates at Windermere Location & Connections

Estates at Windermere sits in the northwest corner of Windermere's 34786 ZIP code, with its single gated entrance on McKinnon Road just north of Lake Butler Boulevard. The position is unusual within the Windermere submarket: it pulls the high-touch luxury character of the older town center while sitting close to the 429 Expressway interchange — most established Windermere estate communities trade location for highway distance, while newer Horizon West communities trade lot size and maturity for highway access. This neighborhood gets both.

The McKinnon Road corridor itself runs north-south between Lake Butler Boulevard and the 429, threading past the Butler Chain of Lakes shoreline communities to the east and the Winter Garden city limits to the west. Downtown Windermere's Town Square sits roughly 3 miles southeast via Conroy-Windermere Road, while Winter Garden Village shopping is approximately 4–5 miles north via the 429.

Estates at Windermere Amenities & Lifestyle

Day-to-day life inside Estates at Windermere centers on the gated single entrance, the interior community park with playground, tennis court, and multipurpose field, and the conservation-area buffers that frame the back edges of many lots. Beyond the gates, residents draw on Windermere's full lifestyle inventory: Town Square dining and the weekly Farmers Market, the Butler Chain of Lakes for boating and watersports, and Winter Garden Village for full-service retail. Golf access is available through nearby clubs on a membership basis — there is no community-owned golf or country club tied to ownership in this neighborhood.

How Estates at Windermere Compares

Estates at Windermere occupies a specific niche in the 34786 market: established custom homes on oversized lots, gated, with no CDD overhead, and in a location that balances Windermere's older luxury character against modern highway access. The clearest comparisons are newer Horizon West luxury subdivisions (more amenities and newer construction, but smaller lots and CDD assessments) and guard-gated estate communities like the Windermere Club next door (larger overall, often higher dues).

Estates at Windermere HOA & CDD Information

Estates at Windermere is governed by a mandatory homeowners association responsible for the gated entry, common conservation areas, the community park, tennis court, and shared landscape maintenance along McKinnon Road frontage. There is no Community Development District (CDD) — a distinguishing feature versus much of the newer luxury construction in southern Windermere and Horizon West.

Architectural standards are enforced through HOA-administered exterior modification reviews. Buyers planning significant renovations, additions, or site changes should request the current covenants, conditions, and restrictions (CC&Rs) and the architectural review process before contract.

Frequently Asked Questions