Winter Garden is a city in Orange County, Florida, with a population of approximately 46,964.
Follow Winter Garden — get updates on meetings, local news, and more.
Meetings
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All events →Apr 17Fridays on the Plaza6:00 PMApr 18Winter Garden Farmers Market7:00 AMApr 24Fridays on the Plaza6:00 PMApr 25Winter Garden Farmers Market7:00 AMApr 25National Prescription Drug Take Back Day9:00 AMMay 1Fridays on the Plaza6:00 PMMay 2Winter Garden Farmers Market7:00 AMMay 2Shop, Dine, & Stroll Raffle-MAY-nia & Live Music9:00 AM
Recent News
All news →NewsAPR 09, 2026
Foundry Arranges $24.5M Sale of Mixed-Use Building in Winter Garden, Florida
Foundry Arranges $24.5M Sale of Mixed-Use Building in Winter Garden, Florida REBusinessOnline
REBusinessOnlineRead article ↗
NewsAPR 03, 2026
Entrepreneur adds $25M piece in downtown Winter Garden buying spree
Entrepreneur adds $25M piece in downtown Winter Garden buying spree Orlando Sentinel
Orlando SentinelRead article ↗
NewsFEB 26, 2026
Small businesses in Winter Garden threatened by property sales
Small businesses in Winter Garden threatened by property sales Spectrum News 13
Spectrum News 13Read article ↗
From Our Blog
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Product
Find Comparable Properties and Appeal Your Assessment — Free Tools Inside
The free Property Tax Check tells you instantly if you're over-assessed. The paid comps tool finds the evidence to prove it — comparable properties, appeal strength scoring, and a downloadable PDF report.
Data & Analysis
Best Suburbs of Chicago to Live In 2026 — Data, Not Opinions
We scored 206 Chicago suburbs across fiscal health and quality of life using real municipal data — crime, taxes, schools, pensions, income, homeownership, and environmental quality. Winnetka, Lake Forest, and Glencoe top the list.
Data & Analysis
Which Illinois Towns Are Going Broke? A Pension Fund Health Check
Illinois faces a 143.7 billion dollar pension crisis. We analyzed which towns are on the brink and what it means for your property taxes.