Home Insurance in Chestertown, Maryland
Homes in Chestertown carry a median value of $344,000 - close to the Kent County median.
The typical home in Chestertown was built around 1982. About 25% of homes were built before 1960, about 7 points below Kent County's 32%. Older homes can cost more to insure or rebuild because of aging wiring, roofing and plumbing.
In Chestertown, the housing stock is 63% single-family homes and 25% apartments in buildings with 5+ units. The rest are 2-4 unit or other housing types.
In Chestertown, about 65% of owner-occupied homes have a mortgage - lenders require hazard insurance on every mortgaged home.
About 52% of occupied homes in Chestertown are owner-occupied. The vacancy rate is 11%; vacant or unoccupied homes typically need a different coverage form than an owner-occupied policy.
Most homes in Chestertown - 82% - are primarily heated with electricity. Homes heated with propane and fuel oil can carry added fire risk. Fuel-tank leaks and spills are often excluded from standard homeowners policies.
FEMA rates Kent County's overall risk as Very Low, led by hurricane (Relatively Low). Kent County had 568 active NFIP flood policies as of September 2026. See the full Kent County home insurance overview for all FEMA hazard ratings and flood coverage details.
The statewide average premium for a standard HO-3 homeowners policy in Maryland is $1,578 per year, according to the NAIC homeowners insurance report (2023 data).
Key figures
| Median home value | $344,000 |
|---|---|
| Median year built | 1982 |
| Owner-occupied share | 52% |
| Share of owner-occupied homes with a mortgage | 65% |
| Top county hazard | Hurricane (Relatively Low) |
| Active NFIP policies in Kent County | 568 |
| Home insurance premium | $1,578 - statewide average (NAIC, 2023 data) |
Nearby towns
Sources
Data last updated: 2026-09-29
- U.S. Census Bureau Gazetteer Files (2024)
- U.S. Census Bureau, American Community Survey 2020-2024 5-Year Estimates (2024)
- FEMA National Risk Index (December 2025)
- FEMA OpenFEMA NFIP Redacted Policies v3 (2026)
- NAIC Dwelling Fire, Homeowners Owner-Occupied, and Homeowners Tenant and Condominium/Cooperative Unit Owners Insurance: Data for 2023 (published 2026) (2023)