2025 Compare Cities Rankings:
Winter Park, FL vs Ocoee, FL

#2 Failure To Lunch

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

#5 Fiscally Fit Cities Report

#6 Stressful Cities 2012

#6 2005 High Gas Prices

#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 Most Popular Cities for the Holidays

#15 Best Cities for Board Gamers

#15 America’s Least Manly Cities

#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 Best Cities for Seniors 2005

#30 Americas Manliest Cites 2011

#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

#2 Failure To Lunch

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

#5 Fiscally Fit Cities Report

#6 Stressful Cities 2012

#6 2005 High Gas Prices

#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 Most Popular Cities for the Holidays

#15 Best Cities for Board Gamers

#15 America’s Least Manly Cities

#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 Best Cities for Seniors 2005

#30 Americas Manliest Cites 2011

#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

I think Winter Park is ideally suited for families and couples, and individuals. It is a beautiful part of Central Florida. There is almost no crime, and it is  More

I've lived in the city for 5 years and certainly, I ??it! Polite people, great schools, nice & very pacific oriented entertainment, family  More

near park  More

Good place to live, especially South of the turnpike (on the other side of West Colonial), Great schools with West Orange High, and Lakeview, Lake Whitney all top A  More