Trailside Station
Trailside Station Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Trailside Station?
Trailside Station is in the Town of Oakland, FL 34760, in west Orange County, about 0.6 miles from Oakland's historic Town Hall.
What types of homes are in Trailside Station?
Trailside Station is all single-family homes. Based on MLS listings and sales from the past 5 years, homes range from about 1,760 to 2,630 square feet with 3 to 4 bedrooms on lots of roughly 9,600 to 17,900 square feet, built from about 2000 to 2002.
How much do homes cost in Trailside Station?
Trailside Station is small, so only a few homes sell each year: there were 11 MLS sales over the past 5 years (September 2026), ranging from about $400,000 to $591,000, with a median around $484,000. For today's listings, see this page.
What are the HOA fees in Trailside Station?
Recent MLS listings (September 2026) show HOA fees of about $30 a month, often billed annually. Ask for the specific home's HOA dues, any CDD amount, and the association rules before making an offer.
What schools serve Trailside Station?
Orange County Public Schools' 2026-27 school zones place Trailside Station in Tildenville Elementary, Lakeview Middle, and West Orange High School.
When were homes in Trailside Station built?
Trailside Station homes were built from about 2000 to 2002.
What is nearby?
Oakland's historic town center, the West Orange Trail and the Oakland Nature Preserve are close to Trailside Station, and downtown Winter Garden's shops, restaurants and Saturday farmers market are a short drive.
