Historic Town of Oakland
Historic Oakland Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is the historic Town of Oakland?
Oakland is a small town in west Orange County, FL 34760, between Winter Garden and the Lake County line. Its historic center is around the historic Town Hall, with the West Orange Trail running through town.
What types of homes are in historic Oakland?
The town's older streets have homes built as early as the 1920s alongside new homes on infill lots. Based on MLS listings and sales from the past 24 months, homes range from about 990 to 3,620 square feet on lots of roughly 3,900 to 14,400 square feet.
How much do homes cost in historic Oakland?
The median sale price for homes on Oakland's historic streets over the past 24 months was about $368,000, based on 11 MLS sales (September 2026), with a wide range from small older homes to new construction near $800,000. For today's numbers, see the listings on this page.
Is there an HOA in historic Oakland?
Recent MLS listings for homes on the town's older streets show no HOA. Newer subdivisions in Oakland, such as Oakland Trails, Longleaf and Briley Farm, do have HOAs. Confirm for any specific property before making an offer.
What schools serve Oakland?
Orange County Public Schools' 2026-27 school zones place Historic Town of Oakland in Tildenville Elementary, Lakeview Middle, and West Orange High School.
What smaller neighborhoods are in Oakland?
Besides the larger communities with their own pages, Oakland includes smaller neighborhoods such as Oakland Heights, Oakland Pointe, Southern Oaks at Oakland Shores, Winters Landing and Trailside Station, where only a few homes sell each year. Their listings appear in the Oakland search.
What is there to do in Oakland?
The West Orange Trail runs through town for walking and cycling, and the Oakland Nature Preserve has a boardwalk out to Lake Apopka. Downtown Winter Garden's shops, restaurants and Saturday farmers market are a short drive.
