2025 Compare Cities Rankings:
Fairfax, VA vs Winter Park, FL

#1 Best Cities for Teleworking - Extra Large Metro Areas

#1 Most Secure Large Cities in the U.S.

#2 Healthiest Cities

#2 Most Difficult Cities to Navigate

#3 Most Irritation Prone Cities

#3 America's Riskiest Online Cities

#4 The Most (and Least) Gender Imbalanced Cities

#4 Best Cities After Military Service

#4 Best Airports to Make a Connection

#5 Sleep in the City Study

#5 Most Secure Places to Live 2011 (Large Metros)

#5 2005 High Gas Prices

#6 America’s Least Manly Cities

#7 Cities on the Edge of Greatness

#7 Failure To Lunch

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

#7 Best States for LGBTQ Rights

#9 Most Secure Places to Live in the U.S. (Large Metro Areas)

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

#9 America's Most Playful Cities

#11 Sperlings Skincare Wrinkle Ranking

#12 Most and Least Risky Places for Identity Theft

#14 The Most Single Cities

#15 Most Competitive Private Colleges

#18 Drought-Riskiest Cities

#18 Best and Worst Cities for Sleep

#19 Most Competitive Public Colleges

#20 Best Cities for Board Gamers

#20 Gloomiest Places in America

#22 Most Popular Cities for the Holidays

#23 Best US Cities for Seniors 2011

#25 Best Cities for Seniors 2005

#26 Fiscally Fit Cities Report

#26 2005 Best Places to Live

#26 Sleepless Cities 2011

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

#29 Most Romantic Cities for Boomers

#31 America's Best and Worst Cities for Crime (Large Metro Areas)

#34 America’s Manliest Sports Cities

#36 Best Baseball Cities

#38 Hypertension Hot Spots

#39 Worst Cities for Respiratory Infections

#40 Best Block Party Places

#42 Americas Manliest Cites 2011

#44 Stressful Cities 2012

#45 America’s Manliest Cities

#45 Most Comfortable Summer Cities

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

#50 Most Energetic Cities

#75 America's Migraine Hot Spots

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

#87 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

I lived in the area for 17 years through high school until I eventually became a truck driver. Having now seen most states extensively, I wanted to fairly review what  More

Living in Fairfax, or any of the Northern Virginia suburbs of DC, means dealing with highways that are a Gordian knot of converging lanes and overpasses, making long  More

The Cost of living here is high. Though the standard of living is also high, unless you're making over 50,000/year, it's difficult to both live and build any sort of  More

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