Oakglen Estates

Oakglen Estates is off East Division Street, with its entrance at Hearthglen Boulevard, on Hearthglen Boulevard and Newhearth Circle. It is inside City of Winter Garden limits, and County GIS shows the West Orange Trail less than half a mile away.

Oakglen Estates has 60 single-family homes, all one-story, built from 2005 to 2007, according to Orange County Property Appraiser records. Homes range from about 1,860 to 3,060 square feet with 3 to 4 bedrooms, on lots of about 0.23 to 0.55 acre. There are no townhomes.

Three homes in Oakglen Estates sold over the past two years (MLS data, October 2026), for about $446,000, $500,000 and $585,000. For today's listings, see the top of this page.

MLS records show different dues figures, so confirm current dues with the association. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Oakglen Estates, but check the property tax bill for any special assessments. The association is Oakglen Estates Homeowners Association, Inc.

Orange County Public Schools' 2026-27 school zones place Oakglen Estates in Dillard Street 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.

Orange County records show no pool on any of the four common tracts the Oakglen Estates association owns, and no shared amenities are confirmed. Some realtor sites mention a pool, so confirm amenities with the association. Oakglen Estates is not related to Oak Glen Apartments in Orlando.

No Oakglen Estates-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.