Canopy Oaks

Canopy Oaks is a charming neighborhood of elegant homes, oak-lined streets, and country ambiance. Located in Winter Garden, Florida, at the intersection of Roper Road and Canopy Woods Way, this gated community features the finest in Central Florida luxury real estate. Beautiful homes and desirable amenities make Canopy Oaks an ideal location to live. Developed by Canopy Oaks Development Company and A.R. Bailey Homes, this luxury Winter Garden community features multiple single-family home plans, with picturesque yards and a variety of layouts. Built between 2017-2019, the 4-6 bedroom homes range in size from 3,665 to 4,671sq. Ft.

Canopy Oaks Homes for Sale

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New
301 New Providence Promenade 301, DAVENPORT

$159,900

301 New Providence Promenade 301, DAVENPORT

2 Beds 2 Baths 1,372 SqFt Residential MLS® # O6448381
New
2222 Majestic Eagle Circle, CLERMONT

$340,000

2222 Majestic Eagle Circle, CLERMONT

3 Beds 2 Baths 1,564 SqFt Residential MLS® # C7531749
New
5446 Knotty Oak Street, MOUNT DORA

$483,990

5446 Knotty Oak Street, MOUNT DORA

3 Beds 2 Baths 2,123 SqFt Residential MLS® # TB8556245
New
5836 Daughtery Downs Loop, LAKELAND

$315,000

5836 Daughtery Downs Loop, LAKELAND

3 Beds 2 Baths 1,686 SqFt Residential MLS® # A4708911
New
1795 Grandiose Drive, LAKE HAMILTON

$298,490

1795 Grandiose Drive, LAKE HAMILTON

4 Beds 2 Baths 1,574 SqFt Residential MLS® # O6448438
New Open House
715 Drawdy Road, BABSON PARK

$247,000

715 Drawdy Road, BABSON PARK

3 Beds 2 Baths 1,858 SqFt Residential MLS® # O6447953
New
1787 Grandiose Drive, LAKE HAMILTON

$296,990

1787 Grandiose Drive, LAKE HAMILTON

4 Beds 2 Baths 1,574 SqFt Residential MLS® # O6448442
New
2463 Aveeno Avenue, HAINES CITY

$432,490

2463 Aveeno Avenue, HAINES CITY

5 Beds 4 Baths 2,878 SqFt Residential MLS® # O6448378
New
26717 Wetlands Way, LEESBURG

$365,000

26717 Wetlands Way, LEESBURG

3 Beds 3 Baths 2,620 SqFt Residential MLS® # G5118826
New
798 Millhorn Loop, THE VILLAGES

$359,000

798 Millhorn Loop, THE VILLAGES

3 Beds 2 Baths 1,500 SqFt Residential MLS® # G5118816
New
7624 Rex Hill Trail, ORLANDO

$350,000

7624 Rex Hill Trail, ORLANDO

3 Beds 2 Baths 1,299 SqFt Residential MLS® # O6448419
New
Timberlane Road, LAKE WALES

$215,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448344
New
Timberlane Road, LAKE WALES

$269,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448343
New Open House
20 Walden, ORMOND BEACH

$349,900

20 Walden, ORMOND BEACH

3 Beds 2 Baths 1,874 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # V4951731
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447200
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447201
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447198
Pending
1624 Sterns Drive, LEESBURG

$285,000

1624 Sterns Drive, LEESBURG

4 Beds 2 Baths 2,936 SqFt Residential MLS® # O6425853
New
3110 Emerald Acres Lane, SANFORD

$374,500

3110 Emerald Acres Lane, SANFORD

3 Beds 3 Baths 1,682 SqFt Residential MLS® # S5159186
New
5714 Cattle Ranch Drive, ST CLOUD

$3,095

5714 Cattle Ranch Drive, ST CLOUD

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6448300
1211 Nixonton Street, DELTONA

$440,000

1211 Nixonton Street, DELTONA

3 Beds 3 Baths 2,208 SqFt Residential MLS® # V4951068
New
140 Bombay Avenue, WINTER SPRINGS

$355,000

140 Bombay Avenue, WINTER SPRINGS

3 Beds 2 Baths 1,373 SqFt Residential MLS® # O6448262
New
31744 Boadwater Ave, LEESBURG

$369,900

31744 Boadwater Ave, LEESBURG

4 Beds 3 Baths 2,626 SqFt Residential MLS® # O6447594
New
5381 Maddie Drive, HAINES CITY

$399,900

5381 Maddie Drive, HAINES CITY

5 Beds 3 Baths 3,011 SqFt Residential MLS® # O6446669
New Open House
1249 Waterwitch Cove Circle, ORLANDO

$874,900

1249 Waterwitch Cove Circle, ORLANDO

3 Beds 3 Baths 2,715 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # O6446291
New
1881 Red Canyon Drive, KISSIMMEE

$310,000

1881 Red Canyon Drive, KISSIMMEE

3 Beds 3 Baths 1,624 SqFt Residential MLS® # O6448530
New
251 Patterson Road D4, HAINES CITY

$105,000

251 Patterson Road D4, HAINES CITY

1 Bed 2 Baths 836 SqFt Residential MLS® # P4940061
344 Sky Valley Street, CLERMONT

$345,000

344 Sky Valley Street, CLERMONT

3 Beds 2 Baths 1,581 SqFt Residential MLS® # O6423173
New
814 Texas Avenue, LAKELAND

$145,000

814 Texas Avenue, LAKELAND

4 Beds 2 Baths 1,312 SqFt Residential MLS® # O6448654
New
14 Apple Hill Hollow, CASSELBERRY

$375,000

14 Apple Hill Hollow, CASSELBERRY

3 Beds 2 Baths 1,288 SqFt Residential MLS® # O6448584

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Canopy Oaks Real Estate Market Statistics

Average Price $1.4M
Lowest Price $1.2M
Highest Price $1.5M
Total Listings 7
Avg. Days On Market 203
Avg. Price/SQFT $342
List to Sell Price Percentage 98 %

Property Types (active listings)

Winter Garden Communities


Multiple floorplans offer 5-8 bedrooms and multi-car garages. Many homes have private pools, perfect to take a dip during warm summer afternoons. The modern security system and gated entry provide privacy and peace of mind. The community features 49 classic estates and a variety of amenities, including a community “post-office,” a children’s play park, and scenic nature trail.

This Winter Garden luxury home community is perfectly situated amongst high-rated schools, world-class dining and entertainment, and convenient area shopping. Easy access to the 429 Expressway and Florida Turnpike make commuting to work or traveling around Orlando a breeze. Enjoy the best of Orlando’s major attractions with short drives to Walt Disney World Resort and Universal Orlando.

Experience the local charm, one of a kind boutiques, and great dining three miles away in Downtown Winter Garden. Daily living and shopping are easy with Stoneybrook West Shopping village and Winter Garden Village less than five miles away. The area boasts many ways to stay active and soak in the Florida weather, including the West Orange Trail, Horizon West Park & Sportsplex, and Forest Lake Golf Club.

Canopy Oaks Community Information

  • Location: Roper Road and Canopy Woods Way
  • Number of Homesites: 49 
  • Built: 2017 - 2019
  • Square Footage: 3,665 to 4,671
  • HOA: Yes 
  • Amenities: Gated Community, Community “post office”, Nature Trails, Children’s play park

Orange County Area Schools

  • Lake Whitney Elementary School: Grades Pre-K - 5th - Distance: 2 miles
  • Sunridge Middle School: Grades 6-8 - Distance: 5 miles
  • West Orange High School: Grades 9th - 12th - Distance: 1 mile

Dining and Shopping

  • Fountains West Shopping Center - Distance: 2.5 miles
  • Downtown Winter Garden - Distance: 2.5 miles
  • Winter Garden Village at Fowler Groves Shopping Center with Super Target - Distance: 6 miles
  • Restaurant Row - Distance: 15 miles
  • The Mall at Millenia, Retail Shopping Centers, Costco, & BJ's Wholesale Club - Distance: 15.5 miles
  • Downtown Orlando - Distance: 18.5 miles

Parks and Recreation

  • Horizon West Park & Sportsplex - Distance: 6 miles
  • West Orange Trail - Distance: 8 miles
  • Roper YMCA Family Center - Distance: 2 miles
  • Walt Disney World - Distance: 15 miles

Hospitals

  • AdventHealth Winter Garden - Distance: 2 miles
  • Health Central Hospital - Distance: 4 miles

*Distances are approximately measured from Canopy Oaks community entrance

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