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Chestertown, MD

Looking to move to Chestertown, MD? You’ve come to the right place. Livability helps people find their perfect places to live, and we’ve got everything you need to know to decide if moving to Chestertown, MD is right for you.

Let’s start with the basics: Chestertown, MD has a population of 5333. What about cost of living in Chestertown, MD? The median income in Chestertown, MD is $45,952 and the median home value is $313,631.

Read on to learn more about Chestertown, MD, and if you’d like some tips and advice for making your big move, check out our Make Your Move page, where you’ll find all kinds of stories and insights including How to Start Over in a New City, Tips for Getting to Know a New City Before You Move and so much more.

Weather in Chestertown, MD

Average Temperatures

64 high / 47 low

Average Annual Rainfall

44 in

Average Annual Snowfall

16 in

Quick Facts about Chestertown, Maryland

Median Home Value
$313,631
Median Property Tax
$2,278
Total Population
5,333
Average Commute
10 min
Median Household Income
$45,952
Median Monthly Rent
$885

Map of Chestertown, MD

Education, Careers and Opportunity in Chestertown, MD

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Data used on Livability.com is provided from the most recent release (November 2025) by Applied Geographic Solutions (AGS). Our LivScore is calculated in partnership with AGS. Sales tax sources: Sales Tax Clearinghouse, Tax Foundation, and State Revenue Departments. Local rates are population-weighted to account for municipal variations.

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