Trails of Winter Garden
Trails of Winter Garden: Local Questions Answered
Where is Trails of Winter Garden?
Trails of Winter Garden is off East Crown Point Road, on Mistflower Lane, Winged Elm Place, Rain Lily Road and Running Oak Lane The West Orange Trail is less than half a mile away. It is inside City of Winter Garden limits.
What types of homes are in Trails of Winter Garden?
Trails of Winter Garden has 62 single-family homes built from 2005 to 2007, according to Orange County Property Appraiser records. Homes range from about 1,610 to 3,050 square feet on lots of about 0.23 to 0.41 acre, and 40 are one-story. There are no townhomes.
How much do homes cost in Trails of Winter Garden?
Four homes in Trails of Winter Garden sold over the past two years (MLS data, October 2026). Based on those four sales, the median was about $485,000, and prices ranged from about $434,000 to $512,000. For today's listings, see the top of this page.
What are the HOA fees in Trails of Winter Garden?
Recent MLS listings show HOA dues of about $54 to $55 per month as of October 2026. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Trails of Winter Garden, but check the property tax bill for any special assessments. The association is The Trails of Winter Garden Homeowners Association, Inc.
What schools serve Trails of Winter Garden?
Orange County Public Schools' 2026-27 school zones place Trails of Winter Garden in Maxey Elementary, Lakeview Middle and Ocoee High School.
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.
Is Trails of Winter Garden the same as Winter Garden Trls 01-3?
Yes. MLS lists sales here under "Winter Garden Trls 01-3," and every address with that name is inside the Trails of Winter Garden plat. It is not Trails of Montverde, Oakland Trails or Parkside Trails, which are separate communities, and it is also separate from Chapin Station.
Can you rent homes in Trails of Winter Garden short term?
No Trails of Winter Garden-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
