Oakland Trails
Oakland Trails 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 Trails?
Oakland Trails is in the Town of Oakland, FL 34760, in west Orange County, about 1.3 miles from Oakland's historic Town Hall, with access to Florida's Turnpike and SR 429.
Who built Oakland Trails?
MLS listings show Oakland Trails homes were built by Meritage Homes, mostly from 2017 to 2020.
What types of homes are in Oakland Trails?
Oakland Trails is all single-family homes. Based on MLS listings and sales from the past 24 months, homes range from about 1,750 to 3,490 square feet with 3 to 5 bedrooms on lots of roughly 3,900 to 7,800 square feet.
How much do homes cost in Oakland Trails?
The median sale price in Oakland Trails over the past 12 months was about $505,000, based on 13 MLS sales (September 2026). Most sales over the past 24 months fell between about $440,000 and $735,000. For today's numbers, see the listings on this page.
What are the HOA fees in Oakland Trails?
Recent MLS listings (September 2026) show Oakland Trails HOA fees of about $105 to $110 a month, often billed quarterly. Ask for the specific home's HOA dues, any CDD amount, and the association rules before making an offer.
What schools serve Oakland Trails?
Orange County Public Schools' 2026-27 school zones place Oakland Trails in Tildenville Elementary, Lakeview Middle, and West Orange High School.
What is nearby?
The West Orange Trail, the Oakland Nature Preserve and Oakland's historic town center are close by, and downtown Winter Garden's shops, restaurants and Saturday farmers market are a short drive.
