Windermere Oaks Homes for Sale

About Windermere Oaks Neighborhood

Windermere Oaks sits on the southern shore of Lake Down, the 886-acre crown-jewel lake of the Butler Chain, in the historic core of the Town of Windermere. The neighborhood is accessed off Conroy-Windermere Road less than a mile east of Downtown Windermere's brick streets, sandwiched between the lake to the north and the Isleworth golf community across the road to the south. With just 14 homes on lots of one acre or larger, it is one of the smallest established lakefront enclaves in the Windermere 34786 ZIP — and one of very few that combines mature 1983-era streetscape with direct deeded frontage on a Butler Chain lake.

The homes were built by various custom builders between 1983 and 2000 in traditional, contemporary, and Florida architectural styles, with sizes ranging from approximately 2,600 to over 8,500 square feet and floor plans typically configured for 3 to 6 bedrooms. Eight of the fourteen properties are lakefront or hold direct water views; six of those eight have full Lake Down frontage with private docks and boat lifts, opening onto the entire 11-lake interconnected chain. The remaining homes sit on heavily wooded interior acre lots with mature live-oak canopy — the feature that gave the community its name.

What sets Windermere Oaks apart from newer Windermere lakefront product is its established character and lot scale. New construction in the area routinely places luxury homes on quarter-acre to half-acre lots; here, every home sits on a full acre or more, with 30+ years of landscaping growth and the natural privacy that comes with it. The location adjacent to Isleworth Golf & Country Club across the road, walking distance to downtown Windermere's Main Street and the 1890 Schoolhouse, the weekly Farmers Market, and a quarter-mile from the public boat ramp on Lake Down means residents get private-island lakefront living without the gated-community price escalation or CDD assessments common to newer chain developments.

Windermere Oaks Location & Connections

Windermere Oaks is positioned on the south shore of Lake Down, less than one mile east of the Town of Windermere's historic core. The neighborhood is bordered by Conroy-Windermere Road on the south — directly across from the entrance to Isleworth — and by Lake Down on the north. S Apopka-Vineland Road is roughly a half-mile east, providing the corridor down to Walt Disney World and up to the SR 408 Expressway and Downtown Orlando. The historic district is anchored by Windermere Town Hall and Town Square, both walking distance from the neighborhood entrance.

Windermere Oaks Amenities & Lifestyle

Windermere Oaks delivers a Butler Chain lifestyle without the gated-community fees. Lake Down access is the centerpiece — boating, water-skiing, paddleboarding, and bass fishing across the 11 interconnected lakes are all reachable from a private dock or, for non-waterfront homes, from the public ramp a quarter-mile from the entrance. Within walking distance of Downtown Windermere, residents tap into the rhythm of the historic-town amenities: the weekly Friday Farmers Market on Main Street, Food Truck Night at Town Square, and the Halloween Costume Parade are all part of the local calendar.

Day-to-day shopping and dining is anchored by The Grove at the corner of Conroy-Windermere Road, with the broader Dr. Phillips Restaurant Row eight to ten minutes south. Residents also have ready access to the wider Windermere network of parks, schools, and clubs covered in the guides below.

How Windermere Oaks Compares

Windermere Oaks competes for buyers who want established Butler Chain lakefront living with acre-plus lots — a profile that only a handful of communities in the 34786 ZIP can match. The closest comparables are guard-gated estate communities and other established Lake Down neighborhoods. The table below highlights structural differences that drive value:

Windermere Oaks HOA & CDD Information

Windermere Oaks operates with a homeowners' association covering common-area items consistent with a small estate community. Because it is not a guard-gated club community, the HOA structure is simpler and the carrying cost considerably lower than at neighbors like Isleworth. The neighborhood does not carry a Community Development District (CDD) bond — common to newer master-planned developments — meaning there is no separate CDD assessment on the annual tax bill.

Frequently Asked Questions