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Median Home Price in Chestertown, MD

The median home value in Chestertown, MD is $397,403 as of 2026-06-30, up 1.37% from a year earlier.

Median Home Value

$397,403

Year-over-Year

+1.37%

Population

5,616

Chestertown ranks #25 of 38 Maryland cities tracked here by median home value, and sits 4.5% below the state's city median of $415,938. It sits in Kent County, where the county-wide median is $392,677.

Crime in Chestertown

Chestertown police recorded a violent crime rate of 232 per 100,000 residents in 2024 — around the middle of the range for reporting cities. Property crime runs at 1,852 per 100,000.

Reported by the city's own police department to the FBI's Uniform Crime Reporting Program (what this covers).

Common questions about Chestertown

How much does a house cost in Chestertown, MD?

The median home value in Chestertown is $397,403. That's up 1.37% from a year earlier. That is about 4.5% below the typical county in Maryland.

Is Chestertown expensive compared to the surrounding area?

Homes in Chestertown are more expensive than Kent County as a whole, where the median is $392,677 — a difference of about 1.2%.

Is Chestertown a safe place to live?

Chestertown police reported 232 violent crimes per 100,000 residents, covering a population of about 5,616. Crime rates are one input among many — they vary block to block within a city, and this figure is a citywide average.