1988 to 2010Years built
2,051 to 11,696 sq ftHome size
GatedEntry
Stoneybrook & East Winter GardenArea
Why people move here

A gated peninsula on Johns Lake, with homes no two alike.

Deer Island sits on its own peninsula on Johns Lake, and it feels like it. The gated community has about 125 homes, many custom, with architecture that changes from lot to lot and sizes that run from about 2,000 to more than 11,000 square feet.
Life here points toward the water: fishing, boating and golf carts are part of the routine, along with a neighborhood park, basketball and tennis. Even with that tucked-away feel, the Turnpike is about a mile northeast and downtown Winter Garden is about five miles. For buyers who want a one-of-a-kind lake home, this is a short list of opportunities each year.
Upsizers looking for a custom lake home with privacy.

Deer Island at a glance

Location: Deer Isle Dr off Colonial Dr (SR 50), about 1 mi southwest of Florida's Turnpike

Builder: Custom and individual builders

Built: 1988 to 2010

Homes: About 125

Home types: Single-family homes

Size: About 2,051 to 11,696 sq ft

Bedrooms: 3 to 7 bedrooms

Entry: Gated

Area: Stoneybrook & East Winter Garden

Life here

What Deer Island has

🚤Lake access for fishing and boating
⛳Golf carts permitted
🌳Neighborhood park
🏀Basketball court
🎾Tennis court
Proximity

What is close to Deer Island

  • Historic Downtown Winter Garden ~5 mi
  • Publix at West Point Commons ~5 mi
  • Winter Garden Village ~7 mi

Approximate distances from the community entrance. Walt Disney World is roughly 15 to 20 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 (K to 5)

🏫 Lakeview Middle (6 to 8)

🏫 West Orange High (9 to 12)

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

The numbers

Deer Island market snapshot

Deer Island had 4 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 Deer Island

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

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

Deer Island homes for sale right now

Straight from Stellar MLS. Save the search and get new Deer Island listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Deer Island?

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

🏡 Buyer Guide

How buying in Deer Island 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

Deer Island FAQ

Where is Deer Island in Winter Garden?

Deer Island is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Deer Isle Dr off Colonial Dr (SR 50), about 1 mi southwest of Florida's Turnpike.

How far is Deer Island from Walt Disney World?

Roughly 15 to 20 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 Deer Island built?

1988 to 2010. Most homes were built by individual or custom builders.

What amenities does Deer Island have?

Lake access for fishing and boating, Golf carts permitted, Neighborhood park, Basketball court, Tennis court.

Is Deer Island a gated community?

Yes. Deer Island has a gated entry. I confirm gate type and access rules for any home before you write an offer.

What schools serve Deer Island?

Schools commonly listed for this community: Tildenville Elementary (K to 5), Lakeview Middle (6 to 8), West Orange High (9 to 12). Assignments change, so verify zoning for a specific address with the OCPS School Locator.

Is Deer Island 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 Deer Island sell for?

Too few homes sold in Deer Island 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 Deer Island from Stellar MLS.

Your next step

Thinking about Deer Island?

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

  • Recent closed sales in Deer Island, 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.