Home › States › Maryland › Chestertown

Median Home Price in Chestertown, MD

The median home value in Chestertown, MD is $396,477 as of 2026-07-31, up 1.55% from a year earlier.

View Chestertown on the interactive city map →

Median Home Value

$396,477

Year-over-Year

+1.55%

Population

5,616

Chestertown ranks #25 of 38 Maryland cities tracked here by median home value, and sits 4.0% below the state's city median of $413,148. It sits in Kent County, where the county-wide median is $392,199.

Housing affordability in Chestertown

Median household income in Chestertown is $54,346, so the typical home value is about 7.3× annual household income. This is a simple price-to-income benchmark rather than a monthly payment estimate; it does not account for mortgage rates, down payments, taxes or insurance.

Household income comes from the U.S. Census Bureau's ACS 5-Year Estimates, table B19013 (how the affordability measure works).

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

What is the average home price in Chestertown, MD?

People often call this an average home price, but the figure shown here is Zillow's typical home value (ZHVI), not a simple arithmetic average. In Chestertown, that value is $396,477. That's up 1.55% from a year earlier. It is about 4.0% below the typical Maryland city tracked here.

Is Chestertown expensive compared to the surrounding area?

Homes in Chestertown are more expensive than Kent County as a whole, where the median is $392,199 — a difference of about 1.1%.

Is Chestertown affordable?

Median household income here is $54,346, so the typical home value is about 7.3× annual household income. This ratio is a broad comparison measure, not a mortgage-payment estimate.

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.