Living in Chestertown, Maryland: homes, schools and costs

The book's checklist

Lower cost of livingEveryday prices run 6.8% below the U.S. average in the parts of Maryland outside metro areas.
More house for the moneyA typical home costs 6.3 years of the typical household's income here. Across the U.S. it's 4.1.
A safer neighborhood19 violent crimes were reported in 2025, about 3.3 per 1,000 people (U.S.: 3.3). Property crime: 13.4 per 1,000 (U.S.: 15.3).
Schools in town2 public schools: 1 elementary and 1 middle. No public high school in town: the nearest is Kent County High, about 5 miles away.
A hospital close byUniversity of Md Shore Medical Ctr at Chestertown is in town and has an emergency room.
Within reach of a big cityBaltimore is about 29 miles away as the crow flies. The book suggests staying within about 60 miles if you'll miss big-city sports, concerts and theater.

A check means Chestertown meets the rule of thumb from Frank and Dave's book. An empty box isn't a deal breaker: it's something to weigh for your family. A question mark means there isn't enough data.

What kind of town

College town. About 1 in 5 residents is a college student, with Washington College in town. Concerts, sports and good food all year, and a big employer that rarely closes. Expect higher home prices close to campus.

The book sorts small towns into six types. These labels come only from the numbers; take the quiz to see which type fits your family.

For a lifetime

Homes and money

Typical home value, as owners valued them in 2020-2024: $344,000U.S.: $332,700
Home prices since then: Up 22%Kent County, 2022 to 2025
Typical rent, with utilities: $1,206 a monthU.S.: $1,413
Typical household income: $54,346U.S.: $80,734
Homes owned by the people living in them: 52%U.S.: 65%
Typical property tax bill: $3,966 a yearMaryland: $4,093
Homes built before 1940: 22%U.S.: 12%
Homes built since 2010: 8%U.S.: 11%
Vacation and seasonal homes: 2%U.S.: 3%
Everyday prices: 93.2U.S. average = 100 (the parts of Maryland outside metro areas)

Home values and rents are what households told the Census Bureau across 2020 to 2024, so they trail today's market: county prices have moved up 22% since 2022. Everyday prices are the government's average for the parts of Maryland outside metro areas, not Chestertown alone. Check current listings before you budget.

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates; Federal Housing Finance Agency, House Price Index for counties (all transactions); U.S. Bureau of Economic Analysis, Regional Price Parities, 2024.

The people

Population, 2025 estimate: 5,6582020: 5,516
Median age: 32.6 yearsU.S.: 38.9
Age 65 and older: 26%U.S.: 17%
Under 18: 16%U.S.: 22%
Adults with a bachelor's degree or more: 53%U.S.: 36%
Moved here from another county or state in the past year: 15%U.S.: 6%
College students: 22%share of all residents

Sources: U.S. Census Bureau, Population Estimates (Vintage 2025); U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Work

Biggest lines of work: Schools, health care and social services (39%); retail (12%); arts, recreation, lodging and restaurants (11%)
Unemployment rate: 4%U.S.: 5%
Average commute: 20 minutesU.S.: 26 minutes
Work from home: 14%U.S.: 15%
Below the poverty line: 12%U.S.: 12%

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Health care

Nearest emergency room: University of Md Shore Medical Ctr at Chestertown, Chestertown, MD, in town. It's a general hospital. Medicare gives it 5 of 5 stars.

Look up doctors, clinics and the hospitals themselves on Medicare's Care Compare. Ask where the most serious cases are sent.

Sources: Centers for Medicare & Medicaid Services, Hospital General Information.

Schools

2 public schools in Chestertown, run by Kent County Public Schools. The nearest public high school is Kent County High, about 5 miles away.

Colleges in or next to town: Washington College (under 1,000 students).

See each school on the federal school search, then check test scores and graduation rates on Maryland's school report card.

Sources: National Center for Education Statistics, Common Core of Data, 2023-24 (via the Urban Institute Education Data Portal); National Center for Education Statistics, IPEDS institution directory, 2024.

Internet

Homes with cable, fiber or DSL internet: 81%U.S.: 76%
Homes with any internet subscription: 84%U.S.: 91%

Before you buy, look up the address on the FCC's National Broadband Map to see which providers serve it.

Sources: U.S. Census Bureau, American Community Survey 2020-2024 5-year estimates.

Weather

January average low: 27°F
July average high: 87°F
Days 90°F or hotter: 37 a year
Nights at or below freezing: 97 a year
Rain and melted snow: 46 inches a year
Snow: 17 inches a year
Elevation: 59 feet

Weather station: Chestertown (1 mile away). Averages for 1991 to 2020.

Sources: NOAA National Centers for Environmental Information, U.S. Climate Normals 1991-2020; U.S. Geological Survey, 3D Elevation Program.

Getting around

Baltimore, MDMetro of 2.9 million29

Straight-line miles. The road is always longer, and as the book says, an interstate at 70 is a different trip from a farm road at 45. Check the real drive: Baltimore.

Kent County is outside any metro area, with 5,000 to 20,000 people in its towns, next to a metro area (USDA rural-urban code 6, on a scale where 1 is the biggest metro areas and 9 the most rural counties).

For a day

24 places on the National Register of Historic Places, including the Chestertown Historic District, Chestertown Historic District (Boundary Increase), Lauretum and Thornton. One is a National Historic Landmark, the country's highest honor for a historic place.

National Park Service sites within about an hour:

Fort McHenry National Monument and Historic Shrine27 miles
Hampton National Historic Site31 miles
National Capital Parks37 miles
Greenbelt Park46 miles
First State National Historical Park46 miles

Campus life. Check Washington College's events calendar for games, concerts and plays open to the public.

Read about Chestertown's history on Wikipedia.

Know Chestertown?

Tell us what a visitor shouldn't miss, and what living there is really like. Write to Main Street at mainstreet@smalltownguide.com. The best notes from people who know the town will be added here.

Nearby

Straight-line miles.

Small towns

Rock Hall, MD1,200 people, 10 miles
Centreville, MD4,800 people, 12 miles
Bowleys Quarters, MD7,000 people, 18 miles
Grasonville, MD3,600 people, 19 miles
Abingdon, MD5,000 people, 20 miles
Joppatowne, MD14,200 people, 20 miles

Smaller places

Kingstown, MD (unincorporated)1,713 people, 2 miles
Worton, MD (unincorporated)126 people, 4 miles
Butlertown, MD (unincorporated)511 people, 5 miles
Fairlee, MD (unincorporated)299 people, 5 miles
Chesapeake Landing, MD (unincorporated)509 people, 6 miles
Church Hill, MD817 people, 7 miles
Kennedyville, MD (unincorporated)205 people, 7 miles
Still Pond, MD (unincorporated)102 people, 8 miles

Sources

Census survey figures are estimates with a margin of error; we leave out any figure whose margin is too wide to be useful. Data last gathered October 5, 2026. See something wrong? Write to mainstreet@smalltownguide.com.