Oakland Hills
Oakland Hills Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Oakland Hills?
Oakland Hills is on East Oakland Avenue in west Orange County, between the Town of Oakland and downtown Winter Garden. Homes have Winter Garden, FL 34787 mailing addresses.
What types of homes are in Oakland Hills?
Oakland Hills is all custom single-family homes. MLS listings describe it as a community of 17 homesites. Based on MLS listings and sales since 2019, homes range from about 3,400 to 5,200 square feet with 4 to 5 bedrooms on lots of roughly 12,600 to 20,500 square feet, built from about 2020 to 2025. Builders named in MLS listings include Justice & Wood and Element Home Builders.
How much do homes cost in Oakland Hills?
Oakland Hills is small, so only a few homes sell each year: there were 9 MLS home sales over the past 5 years (September 2026), ranging from about $1.57 million to $2.42 million, with a median around $1.8 million. Homesites sold for about $310,000 to $315,000 in 2020 and 2021. For today's listings, see this page.
What are the HOA fees in Oakland Hills?
Recent MLS listings (2025 and 2026) show HOA fees of about $300 to $320 a month, billed quarterly. Ask for the specific home's HOA dues, any CDD amount, and the deed restrictions before making an offer.
What schools serve Oakland Hills?
Orange County Public Schools' 2026-27 school zones place Oakland Hills in Tildenville Elementary, Lakeview Middle, and West Orange High School.
Who built the homes in Oakland Hills?
Oakland Hills homes are custom-built. Builders named in MLS listings include Justice & Wood and Element Home Builders, with homes built from about 2020 to 2025.
What is nearby?
The Town of Oakland's historic center, the West Orange Trail and the Oakland Nature Preserve are close to Oakland Hills, and downtown Winter Garden's shops, restaurants and Saturday farmers market are a short drive.
