2025 Compare Cities Rankings:
Winter Garden, FL vs Richmond, VA

#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

#3 Best Places for Military Retirees

#4 Best-Rested Cities 2011

#6 America’s Manliest Sports Cities

#8 2005 High Gas Prices

#10 Best Cities for Teleworking - Medium Metro Areas

#12 America’s Manliest Cities

#12 Most Popular Cities for the Holidays

#12 The Most (and Least) Gender Imbalanced Cities

#13 Most Congested Cities

#13 America's Best Cities for a Healthy Retirement

#15 Worst Cities for Respiratory Infections

#17 Cities on the Edge of Greatness

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

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

#21 Most Romantic Cities for Boomers

#22 Americas Manliest Cites 2011

#23 America's Most Playful Cities

#25 Hypertension Hot Spots

#25 America’s Least Manly Cities

#27 Gloomiest Places in America

#30 America's Top Hygge Cities

#38 Most Energetic Cities

#38 Most and Least Risky Places for Identity Theft

#39 Most Irritation Prone Cities

#43 Failure To Lunch

#43 Best Block Party Places

#44 Best Cities for Board Gamers

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

#47 Drought-Riskiest Cities

#47 Sleepless Cities 2011

#53 The Most Single Cities

#55 2005 Best Places to Live

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

#62 America's Migraine Hot Spots

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

#77 Most Comfortable Summer Cities

#165 Best Green Cities

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

Lived here for a year and it’s not perfect but it’s constantly improving now (areas redevloped, more businesses, job growth). Cost of living is great compared to  More

We love Richmond so much that when we talk about where we'd like to live if we could live anywhere in the US, we always come back to RVA. We live in the city proper  More

I'm an out-of-towner but am coming up on 1 year in Richmond. I would summarize it this way: the best thing and the worst thing about Richmond is its location. I'll  More