Woodlands of Windermere

Woodlands of Windermere is north of Conroy Windermere Road and east of South Hiawassee Road, with entrances from both roads. Homes have Orlando 32835 mailing addresses and are in unincorporated Orange County. The community is not in the Town of Windermere, and it is outside every Census Bureau census-designated place.

Woodlands of Windermere has 108 single-family homes built from 1979 to 1987, and no townhomes or condos, according to Orange County Property Appraiser records. Homes range from about 1,671 to 4,018 square feet with 3 to 5 bedrooms on lots of about 0.33 to 0.64 acre. All but one are one-story, and 91 have a private pool.

Over the past two years (MLS data, October 2026), three homes in Woodlands of Windermere sold, from $450,000 to $667,500. For today's listings, see the top of this page.

Woodlands of Windermere has no mandatory HOA. Orange County's association registry lists Woodlands of Windermere Homeowners Association, Inc. as voluntary, with no master association, so confirm any current dues with the association. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Woodlands of Windermere, but check the property tax bill for any special assessments. Recorded deed restrictions were not reviewed for this page, so confirm any that apply with a title company before buying.

Orange County Public Schools' 2026-27 school zones place Woodlands of Windermere in Windy Ridge K-8, Chain of Lakes Middle and Olympia 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.

No. Woodlands of Windermere is five plats from 1978 to 1986, with 108 homes built from 1979 to 1987 and Orlando 32835 addresses. Woodlands Village touches it on the east but is a separate community of 66 homes built from 1985 to 1994 on streets including Woodlands Village Drive and Shady Wood Lane, with its own mandatory HOA. Woods of Windermere is a separate 2011 plat of 12 homes built from 2012 to 2014, with Windermere 34786 addresses.

Public records reviewed for this page don't show Woodlands of Windermere-specific rental rules. Association membership is voluntary, but recorded deed restrictions were not reviewed for this page, so confirm any that apply with a title company before buying if you plan to rent.