Chestertown, Maryland
2026 Edition · 10 cards · data as of Oct 30, 2026
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Population
Growing. Up 2.6% since 2020.
5,658
people, the 41st-largest of Maryland's cities and towns.
Census Population Estimates, 2025. Rank among Maryland's cities and towns computed by the Almanac. Sources: Census Population Estimates
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The workday
9 in 10 jobs here go to people who live somewhere else.
85.6%
of 4,764 jobs located in Chestertown are filled by in-commuters.
Census LEHD LODES, 2023. Sources: Census LEHD LODES
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Rent
Median rent is up 68% since the 2005–2009 survey, before inflation.
$1,206
a month. Maryland's median is $1,705.
Census ACS 5-year, 2020-2024 (latest), with earlier 5-year windows. Sources: Census ACS 5-year
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The seam
Cross one tract line and median rent jumps $462.
A $462 gap between neighbors, the sharpest rent edge between adjacent tracts in Kent County.
- $1,004 Tract 9504
- $1,466 Tract 9502
Census ACS 5-year, 2020-2024, adjacent tracts compared by the Almanac. Tract estimates carry wide margins of error. Sources: Census ACS 5-year
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Room to build
The median rent sits inside what local wages can carry.
$1,009–$1,514
is the monthly rent range local workforce wages support.
- $1,206 median
Supportable rent computed by the Almanac from 2023 source wage data. Median rent: Census ACS 5-year, 2020-2024. Sources: Computed by the Almanac, Census ACS 5-year
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Building
Most of the housing here is older than 2000.
- 70 homes permitted, 2022–2025
- 54% of those were in multifamily buildings
- 79% of all homes were built before 2000
Census Building Permits Survey, 2022–2025; Census ACS 5-year, 2020-2024. Sources: Census Building Permits Survey, Census ACS 5-year
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Units needed
Closing the gap would add 0.4–1.9% to the 2,465 homes here.
11–48
is the estimated number of missing housing units, from the lowest to the highest of three estimates.
Range computed by the Almanac from 2023 jobs and household data, using three demand models: 1% of jobs located here, 1% of renter households, and a rate by town size applied to renters. The low end is the lowest of the three and the high end the highest. It is an estimate, not a count. Sources: Computed by the Almanac
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Home value
A median home costs 18% less than Maryland's.
$344,000
median home value in Chestertown.
- $344,000 Chestertown
- $419,900 Maryland
- $332,700 U.S.
Census ACS 5-year, 2020-2024. Sources: Census ACS 5-year