Windermere Crossing
Single-family homes · Built 2000 to 2002 · about 1,200+ to 3,700+ sq ft
A tree-lined neighborhood with a lakefront park off Windermere Road.
Windermere Crossing at a glance
Location: Windermere Road and Windermere Crossing Circle
Builder: Custom and individual builders
Built: 2000 to 2002
Homes: 156
Home types: Single-family homes
Size: About 1,200+ to 3,700+ sq ft
Bedrooms: Varies by floor plan
Area: Stoneybrook & East Winter Garden
What Windermere Crossing has
What is close to Windermere Crossing
- Winter Garden Village ~2 mi
- Downtown Winter Garden ~4 mi
- The Grove with Publix Grocery Store ~5 mi
- Shoppes at Belmere ~1.5 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.
Windermere Crossing market snapshot
Windermere Crossing had no 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 Windermere Crossing
Call or text me at 407.502.4719 and I will send every recent closed sale in and around Windermere Crossing, 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.
Windermere Crossing homes for sale right now
Straight from Stellar MLS. Save the search and get new Windermere Crossing listings the day they hit.
Buying or selling in Windermere Crossing?
Pick your guide, tell me where to send it, and it opens right away.
🏡 Buyer Guide
How buying in Windermere Crossing 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.
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If it did not open, use the buttons below. It is yours to keep.
Next step: book a 30 minute call and we will walk through it together for Windermere Crossing.
Windermere Crossing FAQ
Where is Windermere Crossing in Winter Garden?
Windermere Crossing is in east Winter Garden near Stoneybrook West, Daniels Road and Tilden Road, at Windermere Road and Windermere Crossing Circle.
How far is Windermere Crossing 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 Windermere Crossing built?
2000 to 2002. Most homes were built by individual or custom builders.
What amenities does Windermere Crossing have?
Lakefront park, Playground.
Is Windermere Crossing a gated community?
Windermere Crossing is not listed as gated. Ask me about gated options nearby.
What schools serve Windermere Crossing?
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 Windermere Crossing 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 Windermere Crossing sell for?
Too few homes sold in Windermere Crossing 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 Windermere Crossing from Stellar MLS.
Thinking about Windermere Crossing?
Give me 30 minutes and tell me your timeline. I will send back:
- Recent closed sales in Windermere Crossing, 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.