2025 Compare Cities Overview:
Chester, VA vs Winchester, VA

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Highlights
Are people in Winchester older or younger than people in Chester?
- The Median Age in Winchester is 1.8 years younger than in Chester.

Are housing costs cheaper in Winchester or Chester?
- Winchester housing costs are 0.5% more expensive than Chester housing costs.

Which city has a longer commute, Winchester or Chester?
- The average commute for residents of Winchester is 0.8 minutes longer than it is for residents of Chester.

Things to do in Chester?
Chester is an historic city located on the south bank of the James River near Richmond, Virginia. It has a rich history spanning centuries that includes both the Civil War and Revolutionary War eras. The city offers all sorts of attractions such as parks and museums where visitors can learn about its past or take part in outdoor recreation opportunities. There are also many delicious restaurants to enjoy while visiting Chester.

Things to do in Winchester?
Winchester is located in the northern Shenandoah Valley of Virginia. It's a historically significant city known for its rich Civil War history and architectural attractions like Winchester National Cemetery, as well as its numerous outdoor activities like hiking, kayaking, and fishing. The city also boasts an array of art and cultural offerings, with events such as the annual Hillbilly Festival taking place throughout the year.

 Chester, VAWinchester, VAUnited States
 Population  Unlock28,194329,725,481
 Median Income$78,673  Unlock$69,021
 Median Age  Unlock36.638.4
 Avg. Home Price$331,300  Unlock$338,100
 Unemployment Rate  Unlock4.6%6.0%
 Avg. Commute Time23.99  Unlock26.38
Reviews for Chester    6 Reviews

I just recently discovered a little suburb of Richmond, called Chester. Yes, it is small and not much going on in that area - but if you want a peaceful area to live -  More

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I grew up in Chester and it really isn't a bad place to live if you like living in a very populated area. It has great schools, low crime, easy access to both Richmond  More

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Chester, because of its location midway between Richmond, VA and Petersburg, VA, was once just a train station. With residential growth in affluent Chesterfield County  More

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Reviews for Winchester    17 Reviews

I have lived in Winchester for 13 years and I find the locals to be rude, unpleasant and loud. Women worse than men... that's not to say all is bad, the city has some  More

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Over 9 years ago

Worst place I have ever lived. My neighbors hate jemmy since I am not a clone. They do not respect other people's property.I put up a fence and the same day the  More

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I would have to say I agree with much of what another individual wrote: it's like going back in time or living in a place that refuses to adapt to cultural diversity.   More

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