Canopy Oaks Homes for Sale

Gated A.R. Bailey Homes neighborhood under preserved oaks off Roper Road.

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About Canopy Oaks

Canopy Oaks is a gated neighborhood of 49 homes off Roper Road in Winter Garden, between historic downtown Winter Garden and Winter Garden Village at Fowler Groves. It's a community we know about as well as anyone, because we sold it out when it was new and have helped many of those owners sell since.

The name says a lot. When Canopy Oaks was developed in 2016, the grandfather oaks were saved, along with the tree canopy over Roper Road. Driving in feels different from the newer neighborhoods around it.

The homes were built by A.R. Bailey Homes, mostly between 2016 and 2019. The plans run about 3,600 to 4,600 square feet in Mediterranean, Italian and French Country styles, with tile roofs and many private pools. Because one builder did the whole neighborhood, the streets have a consistent look.

Residents have a children's park and nature trails, and with just 49 homes the neighborhood stays small and quiet.

A lot of the original buyers here were physicians relocating to Central Florida, and it's easy to see why. Downtown Winter Garden and the West Orange Trail are a short drive, Winter Garden Village is minutes away, and SR 429 is close for the commute.

If you're thinking about Canopy Oaks, whether you're buying or selling, give us a call. We've spent a lot of time in this neighborhood.

Canopy Oaks Homes for Sale

Active listings in Canopy Oaks, pulled live from the MLS and updated every 15 minutes.

More Winter Garden Neighborhoods

1

Bronson's Landing

Gated neighborhood of about 126 homes near Winter Garden Village and SR 429.

2

Hickory Hammock at Johns Lake

Gated community on Johns Lake with a community dock, pool and fitness center.

3

Lakeshore Preserve

Toll Brothers community on Panther Lake in Horizon West.

4

Waterleigh

Master-planned Horizon West community on Hickorynut Lake.

5

Stoneybrook West

Guard-gated golf community with an Arthur Hills course on Black Lake.

6

Hamlin Reserve

Ashton Woods neighborhood in Hamlin near Lake Hancock and Hamlin Town Center.

7

Watermark

Meritage Homes community in Horizon West with a resort style pool and tennis.

8

Deer Island

Gated community on Johns Lake with one to two acre lots and a community boat ramp.

9

Stanton Estates

45 homes near downtown Winter Garden and the West Orange Trail.

Thinking About Canopy Oaks?

Tell us what you are looking for and we will send you Canopy Oaks homes that fit, including ones the portals do not show. No pressure and no obligation.

Thank you. Sean or Barb will be in touch shortly.

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Sean & Barb AI · Available 24/7

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Hi! I'm Seba, the Sean & Barb AI assistant. I can answer questions about Central Florida luxury neighborhoods, market stats, physician relocation, and more. What's on your mind?

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