Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
1995 to 2007Years built
1,956 to 4,727 sq ftHome size
Varies by floor planBedrooms
North Winter Garden & Lake ApopkaArea
Why people move here

Golf cart district homes beside the West Orange Trail.

Courtlea Oaks puts you in Winter Garden’s golf cart district with the West Orange Trail right beside the neighborhood. About 91 homes built from 1995 to 2007 mix Traditional, Victorian, Cape Cod and Colonial styles, from roughly 2,000 to 4,700 square feet.
Two entrances, one off East Division Street and one off North Dillard Street, keep downtown close. Dillard Street Elementary sits near the Dillard entrance, and Lakeview Middle is about a mile and a half away. Golf cart to dinner on Plant Street, bike the trail in the morning. That is the routine here.
Downsizers and relocators who want the downtown Winter Garden lifestyle.

Courtlea Oaks at a glance

Location: E. Division Street and Forest Haven Drive, with a 2nd entrance on N. Dillard Street and Courtlea Oaks Boulevard

Builder: Custom and individual builders

Built: 1995 to 2007

Homes: 91

Home types: Single-family homes

Size: About 1,956 to 4,727 sq ft

Bedrooms: Varies by floor plan

Area: North Winter Garden & Lake Apopka

Life here

What Courtlea Oaks has

⛳Golf Cart District
🚲Direct Access to the West Orange Trail
Proximity

What is close to Courtlea Oaks

  • Winter Garden Village (Retail, Restaurants, Entertainment) ~3.5 mi
  • Grocery Store (Publix at West Point Commons) ~2 mi
  • Walt Disney World Resort ~12.5 mi
  • Stoneybrook West Golf Club ~5.5 mi

Approximate distances from the community entrance. Walt Disney World is roughly 25 to 30 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

🏫 Dillard Street Elementary

🏫 Lakeview Middle

🏫 West Orange High

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

OCPS school locator
The numbers

Courtlea Oaks market snapshot

$1,000,000Median sale priceLast 12 months.
41 daysDays on marketMedian cumulative days on market.
5Closed sales4 the year before.
99%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

Courtlea Oaks homes for sale right now

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

Start of list of properties

See all Courtlea Oaks homes for sale
Free guides

Buying or selling in Courtlea Oaks?

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

🏡 Buyer Guide

How buying in Courtlea 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

Courtlea Oaks FAQ

Where is Courtlea Oaks in Winter Garden?

Courtlea Oaks is in north Winter Garden between downtown and the Lake Apopka shore, at E. Division Street and Forest Haven Drive, with a 2nd entrance on N. Dillard Street and Courtlea Oaks Boulevard.

How far is Courtlea Oaks from Walt Disney World?

Roughly 25 to 30 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 Courtlea Oaks built?

1995 to 2007. Most homes were built by individual or custom builders.

What amenities does Courtlea Oaks have?

Golf Cart District, Direct Access to the West Orange Trail.

Is Courtlea Oaks a gated community?

Courtlea Oaks is not listed as gated. Ask me about gated options nearby.

What schools serve Courtlea Oaks?

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

Is Courtlea 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 Courtlea Oaks sell for?

Per Stellar MLS, the median sale price in Courtlea Oaks was $1,000,000 across 5 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 Courtlea Oaks?

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

  • Recent closed sales in Courtlea 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
More in North Winter Garden & Lake ApopkaChapin StationCovington ChaseCovington ParkCrown Point SpringsDillard PointeFullers CrossingAll Winter Garden communities
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.