Oakland is a town in Orange County, Florida, with a population of approximately 3,516.
Follow Oakland — get updates on meetings, local news, and more.
Meetings
All meetings →Recent News
All news →NewsMAR 10, 2026
Broward priest faces $500,000 in fines for feeding homeless amid Oakland Park lawsuit
Broward priest faces $500,000 in fines for feeding homeless amid Oakland Park lawsuit CBS News
CBS NewsRead article ↗
NewsMAR 10, 2026
Joseph McMullen wins another term on Oakland Town Commission
Joseph McMullen wins another term on Oakland Town Commission Florida Politics
Florida PoliticsRead article ↗
NewsMAR 10, 2026
Oakland election includes Town Commission race, charter amendments
Oakland election includes Town Commission race, charter amendments Florida Politics
Florida PoliticsRead article ↗
From Our Blog
All posts →
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.