Courtlea Oaks
Courtlea Oaks: Local Questions Answered
Where is Courtlea Oaks in Winter Garden?
Courtlea Oaks is off North Dillard Street at Courtlea Oaks Boulevard, east of downtown, on streets including Courtlea Creek Drive, Valley View Drive and Forest Haven Drive. 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 Courtlea Oaks?
Courtlea Oaks has 91 single-family homes, mostly built from 1995 to 2007, according to Orange County Property Appraiser records. Homes range from about 1,960 to 4,730 square feet on lots of about a third to two-thirds of an acre; 66 are two-story, and 59 have private pools. There are no townhomes.
How much do homes cost in Courtlea Oaks?
Over the past two years (MLS data, October 2026), homes in Courtlea Oaks sold nine times for a median of about $950,000, ranging from about $675,000 to $1.17 million. For today's listings, see the top of this page.
What are the HOA fees in Courtlea Oaks?
Recent MLS listings show HOA dues of about $83 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 Courtlea Oaks, but check the property tax bill for any special assessments. The association is Courtlea Oaks Homeowners Association, Inc.
What schools serve Courtlea Oaks?
Orange County Public Schools' 2026-27 school zones place Courtlea Oaks in Dillard Street 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.
Is Courtlea Oaks the same as Courtlea Park?
No. Courtlea Park is a separate community just north, off East Division Street, on its own 2006 plat, with 42 single-family homes built from 2006 to 2007 and its own association. Courtlea Oaks is the four plats from 1994 to 1999, with 91 homes on larger lots. Both are zoned for the same schools.
Can you rent homes in Courtlea Oaks short term?
No Courtlea 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.
