Wintermere Pointe
Wintermere Pointe Living: Local Insights & FAQs
To help you make informed decisions, we've compiled answers to some of the most commonly asked questions.
Where is Wintermere Pointe in Winter Garden?
Wintermere Pointe is at the northeast corner of Tilden Road and Winter Garden Vineland Road (CR 535), about half a mile south of SR 429, inside City of Winter Garden limits. It is gated, with one gate off Winter Garden Vineland Road and one on Tilden Road.
What types of homes are in Wintermere Pointe?
Wintermere Pointe has 203 single-family homes built from 1999 to 2005, according to Orange County Property Appraiser records. Homes range from about 1,840 to 4,310 square feet, and there are both one-story and two-story homes. There are no townhomes.
How much do homes cost in Wintermere Pointe?
Over the past two years (MLS data, October 2026), homes in Wintermere Pointe sold 17 times for a median of about $625,000, ranging from about $469,000 to $880,000. For today's listings, see the top of this page.
What are the HOA fees in Wintermere Pointe?
Recent MLS listings show HOA dues of about $80 to $91 per month as of October 2026. The HOA website says membership and dues are mandatory. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Wintermere Pointe, but check the property tax bill for any special assessments. The association is Wintermere Pointe Homeowners Association, Inc.
What schools serve Wintermere Pointe?
Orange County Public Schools' 2026-27 school zones place Wintermere Pointe 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 Wintermere Pointe the same as Wintermere Harbor?
No. Orange County plat records show Wintermere Harbor as a separate subdivision just east of Wintermere Pointe, platted in 1999 and 2001, with 91 single-family homes built from 1999 to 2003. Both are inside City of Winter Garden limits. A real estate site notes the two have separate HOAs.
Can you rent homes in Wintermere Pointe short term?
No Wintermere Pointe-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.
