Eastbrook

Eastbrook is north of Aloma Avenue (SR 426) and east of Semoran Boulevard (SR 436), along Eastbrook Boulevard and streets such as Seagrape Drive, Balsam Drive and Conifer Avenue. It has Winter Park addresses but is not inside the City of Winter Park or any other city.

Eastbrook has single-family homes, about 895 in state parcel records, most built from 1958 to 1971. Based on MLS listings and sales from the past two years, homes range from about 1,150 to 1,990 square feet with 3 to 5 bedrooms.

Over the past two years (MLS data, October 2026), homes in Eastbrook sold for a median of about $380,000, with most between about $250,000 and $460,000. For today's listings, see the top of this page.

The neighborhood association's website says membership is completely voluntary, with voluntary dues of $30 a year for owners and tenants and $60 for investors. The association is run by volunteers. Seminole and Orange counties' lists of community development districts don't include Eastbrook, but check the property tax bill for any special assessments.

Seminole County Public Schools' 2026-27 school zones place the Seminole County part of Eastbrook in Eastbrook Elementary, Tuskawilla Middle and Lake Howell High School. Orange County Public Schools' 2026-27 school zones place the Orange County part, at the south end along streets such as Carnation Drive, in Lakemont Elementary, Maitland Middle and Winter Park 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.

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.

Both. State parcel records put about 700 Eastbrook parcels in unincorporated Seminole County and about 200 in unincorporated Orange County, mostly the older units at the south end near Aloma Avenue. The county affects school district and property taxes, so check which county a specific address is in.

No Eastbrook-specific rental rules turned up in our research, and the neighborhood association says membership is voluntary. Deed restrictions and county rules can still apply, so confirm them before buying if you plan to rent.