Winter Oaks
Winter Oaks Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Winter Oaks in Winter Garden?
Winter Oaks is off West Story Road near South Plant Street, west of downtown Winter Garden and north of State Road 50, inside City of Winter Garden limits.
What types of homes are in Winter Oaks?
Winter Oaks has 107 single-family homes built from 2003 to 2007, according to Orange County Property Appraiser records. Homes range from about 1,300 to 3,200 square feet with 2 to 5 bedrooms, and there are both one-story and two-story homes. There are no townhomes.
How much do homes cost in Winter Oaks?
Over the past two years (MLS data, October 2026), homes in Winter Oaks sold nine times for a median of about $582,000, ranging from about $420,000 to $720,000. For today's listings, see the top of this page.
What are the HOA fees in Winter Oaks?
Recent MLS listings show HOA dues of about $146 per month as of October 2026. Orange County's community development district (CDD) map and Property Appraiser records don't show one covering Winter Oaks, but the county map isn't a complete list, so check the property tax bill for any special assessments.
What schools serve Winter Oaks?
Orange County Public Schools' 2026-27 school zones place Winter Oaks in Tildenville Elementary, Lakeview Middle and West Orange 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.
Does Winter Oaks have a community pool?
Two realtor sites mention a community pool in Winter Oaks, though one says the pool is subject to HOA verification. Both also describe the neighborhood as within Winter Garden's golf cart district for trips downtown. Confirm current amenities with the association.
Can you rent homes in Winter Oaks short term?
No Winter Oaks-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.
