2025 Compare Cities Rankings:
Winter Garden, FL vs Delray Beach, FL

#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

#1 Hurricane Hotspots

#2 The Best Cities for Thanksgiving

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

#3 Most Popular Cities for the Holidays

#3 Stressful Cities 2012

#6 Most Difficult Cities to Navigate

#7 The Most Single Cities

#7 Fiscally Fit Cities Report

#8 Best and Worst Cities for Sleep

#12 Best Cities for Teleworking - Extra Large Metro Areas

#13 Best and Worst Airports to make a Connection List

#14 Sperlings Skincare Wrinkle Ranking

#14 Most Irritation Prone Cities

#14 America’s Manliest Sports Cities

#15 Best Airports to Make a Connection

#20 America’s Least Manly Cities

#21 Worst Cities for Respiratory Infections

#23 Most and Least Risky Places for Identity Theft

#24 Cities on the Edge of Greatness

#25 Most Energetic Cities

#27 America's Riskiest Online Cities

#28 Healthiest Cities

#29 Best Baseball Cities

#29 Sleepless Cities 2011

#29 America's Best Cities for a Healthy Retirement

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

#32 Failure To Lunch

#33 The Most (and Least) Gender Imbalanced Cities

#35 Best Cities for Board Gamers

#35 Hypertension Hot Spots

#36 America's Most Playful Cities

#38 Gloomiest Places in America

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

#41 Best Cities for Seniors 2005

#42 America’s Manliest Cities

#43 Sleep in the City Study

#43 Metro Areas with Fastest Rising Income 2020

#44 Americas Manliest Cites 2011

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

#47 Most Competitive Public Colleges

#47 Best Block Party Places

#48 America's Top Hygge Cities

#49 Most Romantic Cities for Boomers

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

#50 Fiscally Fit Cities Report

#57 2005 Best Places to Live

#58 Drought-Riskiest Cities

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

#59 2005 High Gas Prices

#66 America's Migraine Hot Spots

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

#69 2005 Best Places to Live

#81 Most Comfortable Summer Cities

#84 The Most (and Least) Gender Imbalanced Cities

#125 2005 Best Places to Live

#172 Best Green Cities

#241 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

Great place to live, however, the school system isn't great. You really need to pick Boca Raton, or if you're willing to live a bit farther West, Wellington, for better  More

I have lived in over 100 places and homes..even as a child my parents lived moving every few years..i learned to live that too..getting new ideas for decorating and new  More

The area has been totally regentrified over the past 10 years. It's outdoor cafe's and restaurants, shops and, of course, a fabulous beach. the beach has cabanas,  More