Courtlea Oaks

Courtlea Oaks is a single-family Winter Garden community located at E. Division Street and Forest Haven Drive, with a 2nd entrance at N. Dillard Street and Courtlea Oaks Boulevard. Featuring 91 homes, this golf-cart district neighborhood offers 1- and 2-story homes adjacent to the West Orange Trail. Homes here feature a variety of architectural styles, from Traditional to Victorian, Cape Cod to Colonial, and range in size from 3 to 6 bedrooms with 2 to 4.5 bathrooms.

Courtlea Oaks Homes for Sale

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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

Sold Homes in Courtlea Oaks Winter Garden

Real Estate Statistics

Average Price $939K
Lowest Price $939K
Highest Price $939K
Total Listings 1
Avg. Days On Market 75
Avg. Price/SQFT $340
List to Sell Price Percentage 98 %

Property Types (active listings)

Winter Garden Communities

Courtlea Oaks homes offer features like private outdoor pools or fenced yards. Residences may include 2- or 3-car garages. Some homes have fireplaces. On the east side of downtown Winter Garden, residents enjoy access to the golf cart district. Commuters benefit from proximity to the 429 and Florida Turnpike. Courtlea Oaks borders the 22-mile West Orange Trail, making access convenient. Nearby parks, such as Newton Park and Dr. Bradford Memorial Park, offer opportunities to enjoy the Florida lifestyle on Lake Apopka.

Being part of downtown Winter Garden means enjoying weekend farmers market visits, participating in annual town events, and exploring dining and shopping just minutes from the community. These destinations can be reached by golf cart or via the West Orange Trail.

Courtlea Oaks Community Information

  • Location: E. Division Street and Forest Haven Drive, with a 2nd entrance on N. Dillard Street and Courtlea Oaks Boulevard
  • Number of Homesites: 91
  • Year Built: 1995 - 2007
  • Square Footage: 1,956 - 4,727
  • HOA: Yes
  • Community Amenities: Golf Cart District, Direct Access to the West Orange Trail

Orange County Area Schools

  • Dillard Street Elementary School (Grades K-5) - Distance: Adjacent to entrance on N Dillard
  • Lakeview Middle (Grades 6-8) - Distance: 1.5 mile
  • West Orange High School (Grades 9-12) - Distance: 3 miles

Dining and Shopping

  • Downtown Historic Winter Garden - Distance: <0.5 mile
  • Winter Garden Village (Retail, Restaurants, Entertainment) - Distance: 3.5 miles
  • Grocery Store (Publix at West Point Commons) - Distance: 2 miles
  • Plaza Collina with Costco, dining, services - Distance: 6 miles
  • Restaurant Row - Distance: 17.5 miles
  • The Mall at Millenia, Retail Shopping Centers, & BJ's Wholesale Club - Distance:  15.5 Miles
  • Downtown Orlando - Distance: 16 miles

Parks and Recreation

  • Newton Park (Lakefront Playground, fishing, picnics) - Distance: <1 mile
  • Dr. Bradford Memorial Park - Distance: <1 mile
  • Walt Disney World Resort - Distance: 12.5 miles
  • Universal Orlando Resort - Distance: 17 miles
  • West Orange Trail - Distance: Adjacent to the Community
  • Oakland Nature Preserve - Distance: 4.5 miles
  • Stoneybrook West Golf Club - Distance: 5.5 miles
  • Veterans Memorial Park - Distance: 1.5 mile
  • Roper YMCA Family Center - Distance: 3.5 miles

Hospitals

  • AdventHealth Winter Garden - Distance: 3.5 miles
  • HCA Florida West Orange ER - Distance: 1.5 miles
  • Orlando Health-Health Central Hospital - Distance: 5 miles

*Distances are approximately measured from Courtlea Oaks community entrance.

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