Winwood
Winwood: Local Questions Answered
Where is Winwood located?
Winwood is on Winwood Way, entered from the south side of Conroy Windermere Road just east of Dr. Phillips Boulevard, next to Pasatiempo. Homes have Orlando 32819 mailing addresses and are in unincorporated Orange County, outside every Census Bureau census-designated place.
What types of homes are in Winwood?
Winwood has 40 one-story single-family homes built from 1985 to 1988, and no townhomes or condos, according to Orange County Property Appraiser records. Homes range from about 2,048 to 2,952 square feet with 3 to 4 bedrooms on lots of about 0.23 to 0.45 acre, and 32 have a private pool.
How much do homes cost in Winwood?
Over the past two years (MLS data, October 2026), one home in Winwood sold, for $719,000 in November 2024. For today's listings, see the top of this page.
What are the HOA fees in Winwood?
The one recent MLS sale showed HOA dues of about $51 per month. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Winwood, but check the property tax bill for any special assessments. A homeowners association is required, with no master association.
What schools serve Winwood?
Orange County Public Schools' 2026-27 school zones place Winwood in Palm Lake Elementary, 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.
Is Winwood the same as Winderwood or Winderlakes?
No. Winwood is a 1984 plat of 40 homes on the south side of Conroy Windermere Road, with Orlando 32819 addresses. Winderwood is a separate 1986 plat of 49 homes on Winderwood Circle, north of Conroy Windermere Road, with Orlando 32835 addresses and its own association. Winderlakes is also separate, with 202 homes north of Conroy Windermere Road and Orlando 32835 addresses. Wingrove Estates is a separate 1988 plat west of Dr. Phillips Boulevard.
Can you rent homes in Winwood short term?
Public records reviewed for this page don't show Winwood-specific rental rules. HOA documents often limit leasing, so confirm the current rules with the association before buying if you plan to rent.
