1999 to 2003Years built
Varies by floor planHome size
GatedEntry
Stoneybrook & East Winter GardenArea
Why people move here

A gated, landscaped neighborhood near Winter Garden Village.

Wintermere Harbor is a gated community of 83 single-family homes off Winter Garden Vineland Road, built from 1999 to 2003. Mature landscaping gives the neighborhood a finished, settled look.
Winter Garden Village’s shopping and dining are close, and the 429 and the Turnpike make the attractions easy to reach. A gate and a central location at an established-home price make it a good fit for buyers moving up.
Buyers moving up who want a gated home near shopping.

Wintermere Harbor at a glance

Location: Winter Garden Vineland Road and Lakeshore Grove

Builder: Custom and individual builders

Built: 1999 to 2003

Homes: 83 single-family homes

Home types: Single-family homes

Size: Varies by floor plan

Bedrooms: Varies by floor plan

Entry: Gated

Area: Stoneybrook & East Winter Garden

Life here

What Wintermere Harbor has

✨Established neighborhood setting
Proximity

What is close to Wintermere Harbor

  • Winter Garden Village ~1 mi
  • West Point Commons Shopping Center with Grocery Store ~3 mi
  • Historic Downtown Winter Garden ~4 mi
  • Hamlin Town Center ~5 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

🏫 Lake Whitney Elementary

🏫 Sunridge Middle

🏫 West Orange High

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

The numbers

Wintermere Harbor market snapshot

Wintermere Harbor had 1 closed sale 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 Wintermere Harbor

Call or text me at 407.502.4719 and I will send every recent closed sale in and around Wintermere Harbor, 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

Wintermere Harbor homes for sale right now

Straight from Stellar MLS. Save the search and get new Wintermere Harbor listings the day they hit.

Start of list of properties

Free guides

Buying or selling in Wintermere Harbor?

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

🏡 Buyer Guide

How buying in Wintermere Harbor 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

Wintermere Harbor FAQ

Where is Wintermere Harbor in Winter Garden?

Wintermere Harbor is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Winter Garden Vineland Road and Lakeshore Grove.

How far is Wintermere Harbor 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 Wintermere Harbor built?

1999 to 2003. Most homes were built by individual or custom builders.

What amenities does Wintermere Harbor have?

Established neighborhood setting.

Is Wintermere Harbor a gated community?

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

What schools serve Wintermere Harbor?

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

Is Wintermere Harbor 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 Wintermere Harbor sell for?

Too few homes sold in Wintermere Harbor 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 Wintermere Harbor from Stellar MLS.

Your next step

Thinking about Wintermere Harbor?

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

  • Recent closed sales in Wintermere Harbor, 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.