Windermere Crossing
Windermere Crossing: Local Questions Answered
Where is Windermere Crossing in Winter Garden?
Windermere Crossing is off Windermere Road on Windermere Crossing Circle, with connections to Stoneybrook West Parkway at English Garden Lane and Scarlett Sage Court. It borders Lake Reaves and the State Road 429 right-of-way. It is inside City of Winter Garden limits.
What types of homes are in Windermere Crossing?
Windermere Crossing has 156 single-family homes built from 1999 to 2003, according to Orange County Property Appraiser records. Homes range from about 2,170 to 4,300 square feet on lots of about 0.24 to 1.15 acres; 87 are two-story and 69 are one-story. Twelve homes border Lake Reaves. There are no townhomes. Realtor sites name Cambridge Homes as the builder.
How much do homes cost in Windermere Crossing?
Over the past two years (MLS data, October 2026), homes in Windermere Crossing sold four times for a median of about $778,000, ranging from about $680,000 to $865,000. MLS lists these sales under Cambridge Crossing. For today's listings, see the top of this page.
What are the HOA fees in Windermere Crossing?
Recent MLS listings show HOA dues of about $100 to $104 per month as of October 2026. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Windermere Crossing, but check the property tax bill for any special assessments. The association is Cambridge Crossing Phase 1, Phase 1A and Phase 2 Property Owners Association, Inc., which covers all three phases.
What schools serve Windermere Crossing?
Orange County Public Schools' 2026-27 school zones place Windermere Crossing in Lake Whitney Elementary, SunRidge Middle and West Orange High School.
Zoning can change and varies by street, so confirm a specific address with Orange County Public Schools' Find My School tool, and compare school grades in the Florida School Accountability Reports.
Is Windermere Crossing the same as Cambridge Crossing, and is it in Windermere?
Yes, it is the same place. The entrance sign reads Windermere Crossing, but county records, the association and MLS listings use Cambridge Crossing (Phases 1, 1A and 2), so search MLS for Cambridge Crossing. The main street is Windermere Crossing Circle. Despite the name, it is inside City of Winter Garden limits, not the Town of Windermere. Stoneybrook West, next door, is a separate community with its own CDD.
Can you rent homes in Windermere Crossing short term?
No Windermere Crossing-specific rental rules turned up in our research. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
