Windermere Heights

Windermere Heights is just south of Conroy Windermere Road, along Oakland Place, Oak Park Road and Dr. Phillips Boulevard. Homes have Orlando 32819 mailing addresses and are in unincorporated Orange County, not the Town of Windermere. It is outside the Census Bureau's Doctor Phillips census-designated place, but realtor community guides, MLS listings and the Orange Observer's sales reports place it in the Dr. Phillips area.

The Second and Third Sections of Windermere Heights have 62 single-family homes and 2 vacant lots, according to Orange County Property Appraiser records. Most homes were built from 1984 to 1997, with newer custom homes through 2020. Homes range from about 2,090 to 7,110 square feet with 3 to 8 bedrooms, on lots of about a third of an acre to 1.5 acres. There are no townhomes or condos.

Over the past two years (MLS data, October 2026), homes in Windermere Heights sold 6 times for a median of about $1.5 million, ranging from about $1.1 million to $3.1 million. For today's listings, see the top of this page.

No. Realtor sites and MLS listings describe Windermere Heights as having no homeowners association, county records show no association-owned land, and recent MLS listings show no HOA dues. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Windermere Heights, but check the property tax bill for any special assessments.

Orange County Public Schools' 2026-27 school zones place Windermere Heights in Palm Lake Elementary, Chain of Lakes Middle and Olympia 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.

No. Windermere Heights is in unincorporated Orange County, about three-quarters of a mile outside the Town of Windermere limits, according to county GIS. The name comes from its 1925 plats, made by Windermere Investment Co. It is also separate from Hunters Estates, built on the replatted First Section, and from other neighborhoods with Windermere in their names.

No Windermere Heights-specific rental rules turned up in our research, and the neighborhood has no HOA. Deed restrictions and Orange County rules can still limit rentals, so confirm the rules for a specific address before buying if you plan to rent.