Windsong
Windsong: Local Questions Answered
Where is Windsong in Winter Park?
Windsong is inside City of Winter Park limits, along Lake Virginia, Lake Berry and Lake Mizell, on streets such as Genius Drive, Holts Grove Circle, Chapman Circle, Elizabeths Walk and Preserve Point Drive. Homes have Winter Park 32789 addresses. Timberlane Shores is to the west.
What types of homes are in Windsong?
Windsong has 280 single-family homes plus five estate homes in Windsong Estates, according to Orange County Property Appraiser records, mostly built from 2000 to 2017. Most range from about 1,900 to 7,500 square feet, and MLS listings show 4 to 7 bedrooms. About 25 homes are lakefront. There are no condos or townhomes.
How much do homes cost in Windsong?
Over the past two years (MLS data, October 2026), homes in Windsong sold 20 times for a median of about $2.2 million, with most between about $1.3 million and $3.5 million; the highest sale was $7.0 million. For today's listings, see the top of this page.
What are the HOA fees in Windsong?
Recent MLS listings show HOA dues of about $705 to $805 per quarter (about $245 to $268 per month) as of October 2026. The five Windsong Estates homes on Genius Drive were platted in the same series, but confirm their association membership. Orange County property records and Florida's official list of special districts don't show a community development district (CDD) for Windsong, but check the property tax bill for any special assessments. The association is Windsong Community Association, Inc.
What schools serve Windsong?
Orange County Public Schools' 2026-27 school zones place Windsong in Brookshire Elementary, Glenridge Middle and Winter Park 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 Windsong a gated community?
No. Windsong's streets are maintained by the City of Winter Park, and no source describes a community gate. Knowles Place is a Windsong neighborhood and is separate from Lake Knowles Terrace. Windsong is also separate from Kenilworth Shores nearby.
Can you rent homes in Windsong short term?
No Windsong-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.
