Canopy Oaks

Canopy Oaks is off Roper Road, on Canopy Estates Drive and Canopy Woods Way. The plat also touches Beulah Road, and Lake Beulah is less than a mile away. It is inside City of Winter Garden limits.

Canopy Oaks has 49 single-family homes built from 2016 to 2020, according to Orange County Property Appraiser records. Homes range from about 3,600 to 4,930 square feet on lots of about 0.18 to 0.28 acre; all are two-story, and 43 have private pools. There are no townhomes. The Orange Observer reported A.R. Bailey Homes as the builder.

Over the past two years (MLS data, October 2026), homes in Canopy Oaks sold nine times for a median of about $1.33 million, ranging from about $1.2 million to $1.5 million. One home sold twice. For today's listings, see the top of this page.

Recent MLS listings show HOA dues of about $297 to $300 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 Canopy Oaks, but check the property tax bill for any special assessments. A homeowners association owns the common tracts; confirm current dues and rules with the association.

Orange County Public Schools' 2026-27 school zones place Canopy Oaks in Lake Whitney Elementary, SunRidge 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.

Realtor sites describe Canopy Oaks as a gated community off Roper Road. Canopy Oaks Court is a different street, in the Winter Oaks neighborhood, where homes were built in 2004; it is not part of Canopy Oaks. Canopy Oaks is the 2016 plat of 49 homes on Canopy Estates Drive and Canopy Woods Way.

No Canopy 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.