Oakcrest

Oakcrest is on Grand Avenue, Abbey Lane, Cook Lane, Park Vale Boulevard, Silver Place, Beacon Place and part of Grove Avenue. Homes have Winter Park 32792 addresses but are in unincorporated Seminole County, outside Winter Park city limits.

Oakcrest has 135 single-family homes built from 1980 to 1984, according to state parcel records. Homes range from about 1,080 to 2,320 square feet, most on lots of about a fifth of an acre, and MLS listings show 3 to 4 bedrooms. There are no townhomes or condos.

Over the past two years (MLS data, October 2026), homes in Oakcrest sold 5 times for a median of about $360,000, ranging from about $305,000 to $425,000. For today's listings, see the top of this page.

No HOA was found. MLS listings describe Oakcrest as having no HOA and show no HOA fee, and county records show no association-owned land in the plat. Florida's official list of special districts doesn't show a community development district (CDD) for Oakcrest, but check the property tax bill for any special assessments.

Seminole County Public Schools' 2026-27 school zones place Oakcrest in Eastbrook Elementary, Tuskawilla Middle and Lake Howell High School.

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. Woodcrest is a separate neighborhood next door, and Garden Grove is also separate. This page covers the 135 homes in the Oakcrest plat in Plat Book 23, page 67. A different Oakcrest subdivision in Longwood has its own homeowners association, which does not cover these homes.

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