Woodcrest

Woodcrest is off Howell Branch Road, on North Woodcrest Drive, Ferncrest Drive, Fieldcrest Avenue, Blue Jacket Place and nautical-named courts such as Lanyard, Binnacle and Halyard. Homes have Winter Park 32792 addresses but are in unincorporated Seminole County, outside Winter Park city limits.

Woodcrest has 304 single-family homes built from 1969 to 1983, according to state parcel records. Homes range from about 1,020 to 2,550 square feet, most on lots of about a quarter acre, and MLS listings show 3 to 5 bedrooms. The separate Woodcrest condominium is not part of this page.

Over the past two years (MLS data, October 2026), homes in Woodcrest sold 20 times for a median of about $377,000, ranging from about $300,000 to $480,000. For today's listings, see the top of this page.

No mandatory HOA was found. MLS listings describe Woodcrest as having no HOA and show no HOA fee. Florida's official list of special districts doesn't show a community development district (CDD) for Woodcrest, but check the property tax bill for any special assessments.

Seminole County Public Schools' 2026-27 school zones place Woodcrest in Eastbrook Elementary, Tuskawilla Middle and Lake Howell High School. Despite the Winter Park address, Woodcrest is in Seminole County's school district.

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

No. Oakcrest and Eastbrook are separate neighborhoods nearby, and the Woodcrest condominium is a separate property. Woodcrest is also unrelated to Woodcrest Way in Clermont. This page covers the 304 homes in Woodcrest Units 1 to 7.

No Woodcrest-specific rental rules turned up in our research, and no mandatory HOA was found. Deed restrictions and Seminole County rules can still apply, so confirm them before buying if you plan to rent short term.