Downtown Windermere

Downtown Windermere is the original gridded part of the Town of Windermere in Orange County, between Lake Butler on the west and Lake Down on the east, with Windermere 34786 addresses. Main Street runs through the middle. Downtown has no official boundary, so this page covers the grid from West and East 1st Avenue south to about 9th Avenue. A Florida historical marker says the town site was platted in 1889, and the town incorporated in 1925.

Orange County Property Appraiser records show 397 improved residential parcels and 32 vacant residential parcels, with homes built from 1913 to 2025 and a median year built of 1978. Lots range from about 0.07 to 4.31 acres, and 187 of the 397 have a pool on the roll. Zoning is Town of Windermere single-family residential (WND-SFR) on 396 of the 397 parcels.

Over the past two years (MLS data, October 2026), 39 single-family homes sold in Downtown Windermere for a median of about $910,000, with most between about $600,000 and $2.7 million. Sales are matched to the downtown grid by location, and a few homes sold twice in that period. For today's listings, see the top of this page.

Orange County parcel records show no homeowners association owning land in Downtown Windermere and no community development district (CDD). Individual deeds can still carry their own restrictions, so check the title work, and check the property tax bill for any special assessments. A few small subdivisions on the edge of downtown are separate communities, and Manors at Butler Bay has its own HOA.

Orange County Public Schools' 2026-27 school zones place Downtown Windermere in Windermere Elementary, Gotha Middle and Olympia High School. Windermere High School is not the zoned high school.

Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.

Town Hall (520 Main Street, 1922) and the Cal Palmer Memorial Building (1911) are listed on the National Register of Historic Places. Both are individual listings, not the whole area. Fourteen parcels, mostly along Main Street, are in the Town Center Overlay, and a 2023 Orange Observer report on a Main Street development said it follows the Town Center design guidelines and a 35-foot height maximum. Check with the Town before exterior changes.

The FEMA flood map shows 52 of 397 residential parcels in Zone AE and the rest in Zone X, based on a point check of each parcel, not a flood determination. Check an elevation certificate for any address. Lake Butler and Lake Down border downtown. Orange County lists a public boat ramp on Lake Down off Conroy Windermere Road, and a 2023 Orange Observer report said the Town's ramps are resident-only and need a Town park pass.