1999 to 2004Years built
1,950 to 3,750 sq ftHome size
GatedEntry
Stoneybrook & East Winter GardenArea
Why people move here

A palm-lined gated community of 204 homes off Winter Garden Vineland Road.

Wintermere Pointe makes a good first impression with its palm-lined gated entrance. About 204 single-family homes were built here from 1999 to 2004, with entrances off Winter Garden Vineland Road and Tilden Road.
Winter Garden Village is close for shopping and dining, and the 429 is a few minutes away. It is a larger gated community at an established-home price, which makes it a dependable option for buyers moving up.
Buyers moving up who want a gated community near shopping.

Wintermere Pointe at a glance

Location: Winter Garden Vineland Road and Wintermere Pointe Drive or Tilden Road and Rockrose Drive

Builder: Custom and individual builders

Built: 1999 to 2004

Homes: 204 single-family homesites

Home types: Single-family homes

Size: About 1,950 to 3,750 sq ft

Bedrooms: Varies by floor plan

Entry: Gated

Area: Stoneybrook & East Winter Garden

Life here

What Wintermere Pointe has

✨Established neighborhood setting
Proximity

What is close to Wintermere Pointe

  • Winter Garden Village ~2 mi
  • Stoneybrook with Publix Grocery Store ~3 mi
  • West Orange Trail Park ~5 mi
  • Windermere Village ~2.5 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 Pointe market snapshot

$580,000Median sale priceLast 12 months.
37 daysDays on marketMedian cumulative days on market.
13Closed sales4 the year before.
100%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

Wintermere Pointe homes for sale right now

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

Start of list of properties

Free guides

Buying or selling in Wintermere Pointe?

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

🏡 Buyer Guide

How buying in Wintermere Pointe 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 Pointe FAQ

Where is Wintermere Pointe in Winter Garden?

Wintermere Pointe is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Winter Garden Vineland Road and Wintermere Pointe Drive or Tilden Road and Rockrose Drive.

How far is Wintermere Pointe 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 Pointe built?

1999 to 2004. Most homes were built by individual or custom builders.

What amenities does Wintermere Pointe have?

Established neighborhood setting.

Is Wintermere Pointe a gated community?

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

What schools serve Wintermere Pointe?

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 Pointe 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 Pointe sell for?

Per Stellar MLS, the median sale price in Wintermere Pointe was $580,000 across 13 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 Wintermere Pointe?

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

  • Recent closed sales in Wintermere Pointe, 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.