Chestertown, Maryland.
Typical home $386,625 (+1.9% in a year). Baltimore-Columbia-Towson, MD metro.
to buy the typical home at today's mortgage rate — +$1,101 (+119%) since Jan 2020.
- 1 year
- Up $7,158 +2%
- $379,467$386,625 since Sep 2025
- 5 years
- Up $67,182 +21%
- $319,443$386,625 since Sep 2021
Monthly payment to buy the typical home
Home value × that month's 30-year mortgage rate, 20% down, principal and interest. This is the line households feel: prices and rates compound each other.
- Chestertown$2,029
- Maryland$2,230
- United States$1,922
At the last five years' pace, a typical home here doubles in price every 18 years.
Typical home values in Chestertown, MD rose 1.9% over the past year — faster than the nation's +1.2%.
Living in Chestertown, Kent County, Maryland
Chestertown is a town of 5,532 people in Kent County. 52% of its homes are lived in by their owners and 48% are rented. Unemployment in Kent County was 3.7% in August 2026, and the county had 1.2% fewer jobs in 2025 than the year before. The most residents work in schools and health care, then shops.
Written by AI Claude Haiku 5.5 wrote this on 22 October 2026 from the figures here, a list of nearby places and what it knows. It can be wrong or out of date.
What it’s like
The place. Chestertown is a small town on the Chester River, on Maryland's Eastern Shore, and it is the seat of Kent County. Its streets hold many older buildings, and most homes are lived in by their owners. Winters are cold with some snow, summers are warm, and rain falls through much of the year.
Work. Most residents work in schools, hospitals and social care, in shops, in restaurants, hotels and entertainment, or in professional and business services. Job numbers dipped slightly last year, and few people work from home, so most daily work takes place in or near town. Many adults hold a college degree.
Things to do. Charles Sumner Post, Grand Army of the Republic, a museum in or beside town, is the closest place to visit. Further off, the Chester River and the Sassafras River offer water to explore, and the Walters Art Museum is a longer drive away for art.
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- 2,195households
- 53%of adults have a degree
- 12%below the poverty line
- 14%work from home
What residents work in
Employed residents by industry, from the Census survey. Kent County had 7,553 jobs in 2025, 1.2% fewer than the year before (Bureau of Labor Statistics).
Weather through the year
Coldest in January, with highs near 41° and lows near 27°; warmest in July, with highs near 87° and lows near 69°. About 17 inches of snow and 46 inches of rain and melted snow a year.
Average daily high and low, 1991–2020, at the Chestertown weather station, a mile away (NOAA).
Largest workplaces in Chestertown
- Acts Communities of Maryland, Inc. - Heron PointContinuing care retirement communities187
- Chester River Hospital CenterGeneral hospital139FTE
- LaMotte ChestertownPharmaceutical preparations manufacturing137
- Dixon Valve and Coupling CompanyCouplings, hose, metal, manufacturing111
- Redner's Warehouse Market ChestertownGrocery stores92
- Resorts at Chester River ManorSkilled nursing facilities89
- Dixon Valve and Coupling Co. "BOSS" DivisionManufacturing of hose fittings78
- Acme MarketsSupermarkets and other grocery stores64
Staff on average in 2025, as each workplace reported it to OSHA with its injury records: 10 workplaces with 20 or more staff, 984 people in all. Hospitals come from their Medicare cost reports (CMS, 2023); FTE marks full-time equivalent staff. Not listed: many offices and banks, which need not report to OSHA; military bases, whose staff OPM withholds; and, in about half the states, city and county governments.
Natural hazards
- LightningVery high
- Coastal floodingRelatively high
- Strong windRelatively high
- Winter weatherRelatively high
- HurricanesRelatively high
- Heat wavesRelatively high
FEMA’s National Risk Index (December 2025) rates the risk each natural hazard poses to the people, buildings and farms in Chestertown’s census tracts, against the rest of the country; all of them together, relatively moderate. It is meant for planning, not a substitute for a local risk assessment or a flood map: FEMA’s index.
From the U.S. Census Bureau’s 2020 census and its American Community Survey (2020–2024 five-year estimates), and the Bureau of Labor Statistics. A survey, so each figure has a margin of error, and figures it is not sure of are left out. More on Kent County and the Baltimore-Columbia-Towson, MD metro.
Chestertown home values
Zillow measures a city over its municipal boundary. Against the state and national figures, mid-tier homes, smoothed and seasonally adjusted.
- Chestertown$386,625
- Maryland$424,890
- United States$366,157
Sellers are cutting prices on about 1 in 5 Chestertown listings, and the typical home goes pending in 24 days — the market is roughly in balance.
When this market ran hot
Each cell is that month's year-on-year home-value growth. Read left to right, top row is the latest year — the 2021–22 band is the boom.
Market heat, inside the city limits
Share of listings with a price cut
The early-warning dial: sellers cut when buyers stop reaching. Rising cuts cool a market months before prices notice.
- Chestertown22.11%
- United States26.90%
Days to pending
How long the typical listing takes to go under contract.
Not enough data to draw this yet.
Homes for sale
Active for-sale inventory. More supply hands power to buyers.
- Chestertown62
New listings per month
Sellers arriving at the market.
- Chestertown17
Zip codes with a Chestertown address
A different geography, not a breakdown. The figure above covers the municipality; these zips cover everywhere the Post Office calls Chestertown — often including townships beyond the city limits. Both come straight from Zillow, and they are not expected to average out.