2025 Compare Cities Overview:
Annapolis, MD vs Winchester, VA

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Highlights
Are people in Winchester older or younger than people in Annapolis?
- The Median Age in Winchester is 0.9 years younger than in Annapolis.

Are housing costs cheaper in Winchester or Annapolis?
- Winchester housing costs are 39.8% less expensive than Annapolis housing costs.

Which city has a longer commute, Winchester or Annapolis?
- The average commute for residents of Winchester is 1.7 minutes shorter than it is for residents of Annapolis.

Things to do in Annapolis?
Annapolis, Maryland is situated in Anne Arundel County giving visitors leisure areas such as Quiet Waters Park while also having restaurants like The Boatyard Bar & Grill plus entertainment opportunities at Annapolis Towne Centre.

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.

 Annapolis, MDWinchester, VAUnited States
 Population  Unlock28,194329,725,481
 Median Income$92,026  Unlock$69,021
 Median Age  Unlock36.638.4
 Avg. Home Price$552,900  Unlock$338,100
 Unemployment Rate  Unlock4.6%6.0%
 Avg. Commute Time26.45  Unlock26.38
Reviews for Annapolis    31 Reviews

Annapolis has extremely charming areas (mostly old Annapolis neighborhood's)-- Those very old area near the water have Amazing charm. You can start with downtown West  More

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Well, I really would give living in Annapolis 3.5 stars. I moved here by myself several years ago. One of the highs of this place is that there are a lot of terrific  More

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When we were trying to decide where in the USA to relocate to, Annapolis had enough interest that it made our list. Ultimately, we found a different city that offered  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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