2003 to 2007Years built
1,297 to 3,216 sq ftHome size
Varies by floor planBedrooms
Historic Downtown & Plant StreetArea
Why people move here

Golf cart district homes under half a mile from downtown.

Winter Oaks is a neighborhood of 107 homes on the west side of downtown, under half a mile from Plant Street with the West Orange Trail just a couple of blocks away. Homes were built from 2003 to 2007, at about 1,300 to 3,200 square feet.
It is inside the golf cart district, with a community pool and playground. Plant Street dinners and Saturday farmers market runs are a short ride. For downsizers who want to live near downtown, this is a short list.
Downsizers and first move-up buyers who want golf cart access to downtown.

Winter Oaks at a glance

Location: W. Plant Street & Sunset Oaks Road or W. Story Road & Indian Oaks Road, North of Highway 50

Builder: Custom and individual builders

Built: 2003 to 2007

Homes: 107

Home types: Single-family homes

Size: About 1,297 to 3,216 sq ft

Bedrooms: Varies by floor plan

Area: Historic Downtown & Plant Street

Life here

What Winter Oaks has

🏊Community Pool
🛠Playground
⛳Golf Cart District
🚲0.2 mile to West Orange Trail
Proximity

What is close to Winter Oaks

  • Winter Garden Village (Retail, Restaurants, Entertainment) ~4 mi
  • Grocery Store (Publix at West Point Commons) ~2 mi
  • Walt Disney World Resort ~13 mi
  • West Orange Trail ~0.2 mi

Approximate distances from the community entrance. Walt Disney World is roughly 20 to 25 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

🏫 Tildenville Elementary

🏫 Lakeview Middle

🏫 West Orange High

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

The numbers

Winter Oaks market snapshot

$640,000Median sale priceLast 12 months.
21 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

Winter Oaks homes for sale right now

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

Start of list of properties

Free guides

Buying or selling in Winter Oaks?

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

🏡 Buyer Guide

How buying in Winter 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

Winter Oaks FAQ

Where is Winter Oaks in Winter Garden?

Winter Oaks is in historic downtown Winter Garden near Plant Street and the West Orange Trail, at W. Plant Street & Sunset Oaks Road or W. Story Road & Indian Oaks Road, North of Highway 50.

How far is Winter Oaks from Walt Disney World?

Roughly 20 to 25 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 Winter Oaks built?

2003 to 2007. Most homes were built by individual or custom builders.

What amenities does Winter Oaks have?

Community Pool, Playground, Golf Cart District, 0.2 mile to West Orange Trail.

Is Winter Oaks a gated community?

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

What schools serve Winter Oaks?

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

Is Winter 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 Winter Oaks sell for?

Per Stellar MLS, the median sale price in Winter Oaks was $640,000 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 Winter Oaks?

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

  • Recent closed sales in Winter 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®

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.