The typical owner-occupied home in Chestertown is worth about $344,000, 18% below the Maryland median of $419,900 and 3% above the national median of $332,700. Owners pay a median $3,966 a year in property taxes, about 1.15% of their home's value, higher than the Maryland rate of 0.97%. The median household earns $54,346 a year, so the median home costs 6.3 times the median income (4.1 times for Maryland). 52% of occupied homes here are lived in by their owners, and 65% of those owners still have a mortgage.
Chestertown at a glance
| Chestertown | Maryland | U.S. | |
|---|---|---|---|
| Median home value | $344,000 | $419,900 | $332,700 |
| Median property tax paid per year | $3,966 | $4,093 | $3,119 |
| Property tax as a share of value | 1.15% | 0.97% | 0.94% |
| Median household income | $54,346 | $103,678 | $80,734 |
| Homes lived in by their owners | 52% | 68% | 65% |
| Owner homes with a mortgage | 65% | 71% | 61% |
| Median monthly costs, owners with a mortgage | $2,144 | $2,347 | $1,963 |
| Those costs as a share of the owners' income | 27.2% | 20.5% | 21.0% |
| Median rent | $1,206 | $1,705 | $1,413 |
| Rent as a share of renters' income | 36.7% | 30.8% | 30.6% |
| Median year homes were built | 1982 | 1979 | 1980 |
| Vacant homes | 11.0% | 7.7% | 10.1% |
| Population | 5,594 | 6,206,011 | 334,922,499 |
What a typical home costs per month in Chestertown
At this week's average 30-year rate of 7.11%, buying the median Chestertown home of $344,000 with 20% down costs about $2,324 a month, including property taxes and insurance. With an FHA loan and 3.5% down, it's about $2,897, because the loan is bigger and FHA adds mortgage insurance.
Lenders usually want housing costs under about 28% of gross income, which means an income of roughly $99,612 for the 20%-down payment. That payment is 51% of the median Chestertown household income of $54,346; at that income and 20% down, the 28% guideline points to a home of about $188,000.
The median rent here is $1,206 a month, so owning the median home costs about $1,118 a month more than renting, before you count the equity you build and any tax benefits.
| Down payment | $68,800 |
|---|---|
| Loan amount | $275,200 |
| Principal and interest | $1,851 |
| Property taxes (1.15% a year) | $330 |
| Homeowners insurance (our estimate, 0.5% a year) | $143 |
| PMI | $0 |
| Total per month | $2,324 |
Change the numbers in the calculator
| Down payment | $12,040 |
|---|---|
| Loan amount | $337,769 |
| Principal and interest | $2,272 |
| Property taxes (1.15% a year) | $330 |
| Homeowners insurance (our estimate, 0.5% a year) | $143 |
| FHA mortgage insurance | $152 |
| Total per month | $2,897 |
Change the numbers in the calculator
Questions about home buying in Chestertown
What is the median home value in Chestertown?
About $344,000 for owner-occupied homes, according to the Census Bureau's 2020–2024 American Community Survey.
How much are property taxes in Chestertown?
Homeowners pay a median $3,966 a year, which is about 1.15% of the median home value. Your bill depends on your home's assessed value and local rates.
What income do you need to buy a home in Chestertown?
For the median home with 20% down at 7.11%, the payment is about $2,324 a month. Keeping that under 28% of gross income takes about $99,612 a year.
More about Chestertown
- Mortgage Refinance in Chestertown
- Debt Relief in Chestertown
- Home Equity Loans in Chestertown
- Guides and quotes for mortgage refinance on our sister site, MortgageRefinance.com
Sources: U.S. Census Bureau, American Community Survey 2020–2024 5-year estimates; Freddie Mac Primary Mortgage Market Survey, week of November 12, 2026. Estimates for small places have wide margins of error. About our data