Schedule a 30 Minute AppointmentCall or Text Jorge: 407.502.4719WhatsApp Jorge
Mostly 1939 to 1953Years built
700 to 1,100 sq ftHome size
Varies by floor planBedrooms
Historic Downtown & Plant StreetArea
Why people move here

Historic homes in the heart of downtown Winter Garden.

Shadow Lawn is one of downtown Winter Garden’s historic neighborhoods, with about 144 homes, many built between 1939 and 1953. It sits just south of Plant Street, framed by Maple Street, Dillard Street and Story Road.
You are minutes on foot from Plant Street dining, the farmers market and the West Orange Trail. Older homes here have character you cannot build new, and many have been updated. For downsizers and relocators who want true downtown living, this is the real thing.
Downsizers and relocators who want historic charm and a walkable downtown.

Shadow Lawn at a glance

Location: E Maple St (north), S Dillard St (west), Summer St and Winter St (east), E Story Rd (south)

Builder: Custom and individual builders

Built: Mostly 1939 to 1953

Homes: About 144

Home types: Single-family homes

Size: About 700 to 1,100 sq ft

Bedrooms: Varies by floor plan

Area: Historic Downtown & Plant Street

Life here

What Shadow Lawn has

✨Established neighborhood setting
Proximity

What is close to Shadow Lawn

  • Grocery Store (Publix at West Point Commons) ~1 mi
  • Winter Garden Village ~3 mi
  • Stoneybrook West Village ~5 mi
  • Downtown Winter Garden ~1 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

🏫 Maxey Elementary

🏫 Lakeview Middle

🏫 West Orange High

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

OCPS school locator
The numbers

Shadow Lawn market snapshot

Shadow Lawn had 2 closed sales in the last 12 months. That is too few for a median that means anything, so I price homes here one at a time.

Get the real numbers for Shadow Lawn

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Shadow Lawn, straight from Stellar MLS, with what each one tells us about value.

Request a custom report

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

Shadow Lawn homes for sale right now

Straight from Stellar MLS. Save the search and get new Shadow Lawn listings the day they hit.

Start of list of properties

See all Shadow Lawn homes for sale
Free guides

Buying or selling in Shadow Lawn?

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

🏡 Buyer Guide

How buying in Shadow Lawn 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

Shadow Lawn FAQ

Where is Shadow Lawn in Winter Garden?

Shadow Lawn is in historic downtown Winter Garden near Plant Street and the West Orange Trail, at E Maple St (north), S Dillard St (west), Summer St and Winter St (east), E Story Rd (south).

How far is Shadow Lawn 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 Shadow Lawn built?

Mostly 1939 to 1953. Most homes were built by individual or custom builders.

What amenities does Shadow Lawn have?

Established neighborhood setting.

Is Shadow Lawn a gated community?

Shadow Lawn is not listed as gated. Ask me about gated options nearby.

What schools serve Shadow Lawn?

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

Is Shadow Lawn 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 Shadow Lawn sell for?

Too few homes sold in Shadow Lawn in the last 12 months for a reliable median. Call or text me at 407.502.4719 and I will send recent closed sales in and around Shadow Lawn from Stellar MLS.

Your next step

Thinking about Shadow Lawn?

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

  • Recent closed sales in Shadow Lawn, 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 Historic Downtown & Plant Street30 North ParkEdgewater BeachHeritage at Plant StreetLakeview Village EstatesOaks at Brandy LakePark Avenue EstatesAll 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.