Winterset

Winterset is at the corner of East Canton Avenue and North Interlachen Avenue, one block from Park Avenue. It is inside City of Winter Park limits, and units have Winter Park 32789 addresses.

Winterset has 31 condominium units, all built in 1971, according to Orange County Property Appraiser records. Units range from about 730 to 1,900 square feet with 1 to 3 bedrooms, most with two, and MLS listings describe a mid-rise building with elevators. There are no single-family homes.

Over the past two years (MLS data, October 2026), units in Winterset sold 6 times for a median of about $599,000, ranging from about $464,000 to $775,000. For today's listings, see the top of this page.

Recent MLS listings show condominium association dues of about $859 to $1,039 per month as of October 2026; a double unit listed higher. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Winterset, but check the property tax bill for any special assessments.

Orange County Public Schools' 2026-27 school zones place Winterset in Lakemont Elementary, Maitland Middle and Winter Park 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. Winterset is a secured-entry building: MLS listings describe a lobby with key or code access and a call box for guests, not a gated community. Winterset is separate from Andalucia, a condominium one block north on North Interlachen Avenue.

No Winterset-specific rental rules turned up in our research. Condominium documents often limit leasing, and many MLS listings note that buyers need association approval, so confirm the current rules with the association before buying if you plan to rent.