Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
2017 to 2019Years built
3,665 to 4,671 sq ftHome size
GatedEntry
Stoneybrook & East Winter GardenArea
Why people move here

49 gated estate homes under an oak canopy off Roper Road.

Canopy Oaks feels like country living with a Winter Garden address. Oak-lined streets wind through a gated community of 49 homes off Roper Road, built from 2017 to 2019 by A.R. Bailey Homes, with sizes from roughly 3,700 to 4,700 square feet.
Nature trails, a play park and even a small community post office add to the character. West Orange High is about a mile away and Winter Garden Village is a short drive. For upsizers who want an estate-size home with privacy, Canopy Oaks has very little turnover, so I watch it closely.
Upsizers looking for an estate home with privacy and character.

Canopy Oaks at a glance

Location: Roper Road and Canopy Woods Way

Builder: Custom and individual builders

Built: 2017 to 2019

Homes: 49

Home types: Single-family homes

Size: About 3,665 to 4,671 sq ft

Bedrooms: Varies by floor plan

Entry: Gated

Area: Stoneybrook & East Winter Garden

Life here

What Canopy Oaks has

🛡Gated Community
✨Community “post office”
🚲Nature Trails
🌳Children’s play park
Proximity

What is close to Canopy Oaks

  • Downtown Winter Garden ~2.5 mi
  • Winter Garden Village at Fowler Groves Shopping Center with Super Target ~6 mi
  • West Orange Trail ~8 mi
  • Walt Disney World ~15 mi

Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 minutes away off-peak. SR 50, the 429 interchanges and Avalon Road back up at rush hour, so send me your work address and I will map your real commute.

Schools

🏫 Lake Whitney Elementary

🏫 Sunridge Middle

🏫 West Orange High

Orange County Public Schools. Zoning changes, so verify every address.

OCPS school locator
The numbers

Canopy Oaks market snapshot

$1,330,000Median sale priceLast 12 months.
21 daysDays on marketMedian cumulative days on market.
7Closed sales2 the year before.
98%Sale-to-list price ratioMedian for the last 12 months.

Stellar MLS, residential closed sales, 12 months ending September 30, 2026. Pulled Oct 16, 2026 and refreshed every quarter. Deemed reliable but not guaranteed. For a specific home, request a custom report.

Live MLS listings

Canopy Oaks homes for sale right now

Straight from Stellar MLS. Save the search and get new Canopy Oaks listings the day they hit.

Start of list of properties

Active, 665 CANOPY ESTATES DRIVE, , ,press enter for more details, To favorite this property press control+s.
$1.5m
$335
Active
665 CANOPY ESTATES DRIVE
Winter Garden, FL 34787
5
Beds
,
5
Baths
,
4,479
square feet,
Virtually Staged. EXCEPTIONAL LUXURY IN THE HEART OF WINTER GARDEN! Welcome to this stunning 5-bedroom, 4.5-bathroom pool home nestled within Canopy Oaks, an exclusive, Parade of Homes award-winning gated community featuring just 49 residences. This beautifully upgraded Lockhart II model delivers an exceptional blend of elegance, comfort, and sophistication, featuring TWO luxurious primary suites, one on each floor, a 3-car garage, and private front and rear balconies. Step through the magnificent arched double doors into a breathtaking two-story foyer, where timeless architectural details and modern finishes set the tone. The thoughtfully designed interior showcases a versatile office or flex space, an exquisite wine cellar with authentic Chicago brick flooring, and a gourmet kitchen featuring a 5-burner natural gas cooktop and oversized island. A beautiful wooden staircase with custom forged-iron railings leads upstairs to generously sized bedrooms, a spacious primary suite with an impressive walk-in closet, and a dedicated home theater complete with a movie projector. RECENT UPGRADES includes 2025 A/C system, contemporary light fixtures, updated countertops, fresh interior paint, new downstairs flooring, custom closets, and a beautifully remodeled backyard. Step outside into your private retreat, featuring a sparkling pool and an inviting setting for entertaining or unwinding. LOCATION IS EVERYTHING! Just minutes from Winter Garden Village and Historic Downtown Winter Garden, enjoy convenient access to premier shopping, exceptional dining, and entertainment. With easy connections to Florida’s Turnpike, SR 429, SR 408, and Highway 50, the best of Central Florida is within easy reach. Luxury, exclusivity, and an unbeatable location come together in one extraordinary home. Schedule your private showing today!
Residential
MLS# O6451775 Wra Business & Real Estate
More Details
See all Canopy Oaks homes for sale
Free guides

Buying or selling in Canopy Oaks?

Pick your guide, tell me where to send it, and it opens right away.

🏡 Buyer Guide

How buying in Canopy Oaks works, from new construction versus resale to what to verify on HOA, CDD and school zoning.

🔑 Seller Guide

Pricing, prep and timing for selling your current home, including how to sell and buy at the same time without moving twice.

Questions buyers ask

Canopy Oaks FAQ

Where is Canopy Oaks in Winter Garden?

Canopy Oaks is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Roper Road and Canopy Woods Way.

How far is Canopy Oaks from Walt Disney World?

Roughly 15 to 20 minutes off-peak from this part of Winter Garden. I will map the exact drive from the entrance before you choose.

When were homes in Canopy Oaks built?

2017 to 2019. Most homes were built by individual or custom builders.

What amenities does Canopy Oaks have?

Gated Community, Community “post office”, Nature Trails, Children’s play park.

Is Canopy Oaks a gated community?

Yes. Canopy Oaks has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Canopy Oaks?

Schools commonly listed for this community: Lake Whitney Elementary, Sunridge Middle, West Orange High. Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Canopy Oaks inside Winter Garden city limits?

Many homes with a Winter Garden 34787 address, including much of Horizon West, sit in unincorporated Orange County rather than the City of Winter Garden. Taxes, utilities and services differ, so I confirm the jurisdiction for every address.

What do homes in Canopy Oaks sell for?

Per Stellar MLS, the median sale price in Canopy Oaks was $1,330,000 across 7 closed sales in the 12 months ending September 30, 2026. Call or text me at 407.502.4719 for recent sales that match your home.

Your next step

Thinking about Canopy Oaks?

Give me 30 minutes and tell me your timeline. I will send back:

  • Recent closed sales in Canopy Oaks, straight from Stellar MLS
  • City or county, HOA and CDD for the homes that fit
  • Your real commute, mapped from the entrance

No pressure. If you are selling a home somewhere else first, we will plan both sides together.

Semper Fi to your real estate needs. Jorge Martinez, REALTOR®

Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719
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Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge

Information deemed reliable but not guaranteed. Community details come from public sources and change over time; distances are approximate. Market data from Stellar MLS. Buyers should verify city or county jurisdiction, school assignments, HOA, CDD, lake access and all property details independently. The JEM Property Group is an independently owned and operated real estate team affiliated with Keller Williams Realty. Equal Housing Opportunity.