2025 Compare Cities Cost of Living:
Chestertown, MD vs Enterprise, AL

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Highlights
Is it cheaper to live in Enterprise or is it cheaper to live in Chestertown?
- Enterprise is 12.4% less expensive than Chestertown.

Which city has more affordable housing, Enterprise or Chestertown?
- Enterprise housing costs are 42.0% less expensive than Chestertown housing costs.

Is Health Care more affordable in Chestertown or is Health Care more affordable in Enterprise.
- Health related expenses are 38.0% more in Enterprise.
 Chestertown, MDEnterprise, ALUnited States
 Overall  Unlock79.2100
 Food & Groceries100.8  Unlock100
 Health  Unlock115.8100
 Housing91.0  Unlock100
 Median Home Cost  Unlock$191,100$338,100
 Utilities106  Unlock100
 Transportation  Unlock67.6100
 Miscellaneous81.5  Unlock100
100 = National Average (Below 100 means cheaper than the US average. Above 100 means more expensive.)
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Reviews for Chestertown    3 Reviews

I have lived in Queen Anne's county most of my life, which is on the other side of the river from Chestertown. When I was younger, I remember ice cream shoppes, music  More

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Over 18 years ago

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More

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Over 18 years ago

Chestertown is lovely. Because of the College, it has a real college town feel. It is very old however, so there are many people whose families grew up here. They make  More

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Reviews for Enterprise    5 Reviews

Over 6 years ago

It's not that bad to be honest, people who move here are military or retirement. Very peaceful, but a 4- star rating because some of the things in this county aren't  More

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Over 15 years ago

Enterprise is a small town with good people. Not a lot to do in town but some of the best beaches in the world are only 2 hours away. Easy going slow pace of life.  More

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Over 16 years ago

small town with Large Army base, FT. Rucker as influence, summers hot, winter cool to cold, only two  More

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