2025 Compare Cities Rankings:
Oakland, TN vs Winter Garden, FL

#1 Hypertension Hot Spots

#3 The Most (and Least) Gender Imbalanced Cities

#4 Americas Manliest Cites 2011

#4 America’s Manliest Sports Cities

#5 Most Congested Cities

#10 Best Block Party Places

#11 The Most Single Cities

#11 America’s Manliest Cities

#20 Worst Cities for Respiratory Infections

#20 Best Cities for Teleworking - Medium Metro Areas

#22 Most Irritation Prone Cities

#24 Most Energetic Cities

#24 Best Baseball Cities

#27 2005 High Gas Prices

#28 Second Annual “America’s Manliest Cities” Rankings

#28 Gloomiest Places in America

#30 Sleepless Cities 2011

#33 Drought-Riskiest Cities

#36 Failure To Lunch

#37 Most Popular Cities for the Holidays

#38 America's Most (and Least) Stressful Cities (100 Largest Metro Areas)

#39 Most and Least Risky Places for Identity Theft

#41 Metro Areas with Fastest Rising Income 2020

#41 America's Top Hygge Cities

#45 High Gas Prices - Which Cities are Hit the Hardest?

#46 America’s Least Manly Cities

#48 Cities on the Edge of Greatness

#48 America's Most Playful Cities

#48 America's Riskiest Online Cities

#48 America's Best Cities for a Healthy Retirement

#50 Best Cities for Board Gamers

#50 Most Romantic Cities for Boomers

#51 America's Migraine Hot Spots

#66 America’s Best (and Worst) Cities for Dating

#79 Most Comfortable Summer Cities

#109 2005 Best Places to Live

#339 Best Green Cities

#2 Failure To Lunch

#5 Fiscally Fit Cities Report

#5 High Gas Prices - Which Cities are Hit the Hardest?

#6 2005 High Gas Prices

#6 Stressful Cities 2012

#7 Sleepless Cities 2011

#8 Best Cities for Teleworking - Large Metro Areas

#9 America’s Manliest Sports Cities

#10 Sperlings Skincare Wrinkle Ranking

#11 Most Irritation Prone Cities

#14 America’s Manliest Cities

#15 Drought-Riskiest Cities

#15 America’s Least Manly Cities

#15 Most Popular Cities for the Holidays

#15 Best Cities for Board Gamers

#16 Second Annual “America’s Manliest Cities” Rankings

#18 Worst Cities for Respiratory Infections

#19 Most Romantic Cities for Boomers

#20 Most and Least Risky Places for Identity Theft

#21 America's Most (and Least) Stressful Cities (100 Largest Metro Areas)

#22 Best and Worst Airports to make a Connection List

#23 America’s Best (and Worst) Cities for Dating

#27 Best Block Party Places

#29 Hypertension Hot Spots

#30 Americas Manliest Cites 2011

#30 Best Cities for Seniors 2005

#31 Most Energetic Cities

#32 Wrinkle Ranking Cities Most at Risk for Skin Damage by 2040

#34 America's Most Playful Cities

#34 Best Airports to Make a Connection

#35 America's Best Cities for a Healthy Retirement

#36 The Most Single Cities

#37 Best and Worst Cities for Sleep

#38 Cities on the Edge of Greatness

#38 America's Top Hygge Cities

#40 Gloomiest Places in America

#44 Best Baseball Cities

#46 Healthiest Cities

#49 Metro Areas with Fastest Rising Income 2020

#76 America's Migraine Hot Spots

#96 Most Comfortable Summer Cities

#97 The Most (and Least) Gender Imbalanced Cities

#134 2005 Best Places to Live

#143 Best Green Cities

No Recreation Department available. One park available for kids, and your child must be a student at that  More

Great cost for home for the money! Less than $79 per square foot for a really nice home. Real estate taxes only .0047, so on a home Valued at $303,000 you would only pay  More

Great town  More

Winter Garden has a nice community feel although it's part of the metro Orlando area. The downtown area has several shops and restaurants with a bike trail that leads  More

Central Florida's quality of life is rapidly deteriorating from what it once was. Growing crime, uncontrolled sprawl, nightmarish traffic, poor public transportation and  More