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Rental Market Trends in Chestertown, MD

What is the average rent in Chestertown, MD?

$1,306/month

Average Rent

754 Sq Ft

Average Apartment Size

+2.7%

Increase in the Last Year

As of September 2025, the average rent in Chestertown, MD is $1,306 per month. This is 20% lower than the national average rent of $1,639/month, making renting in Chestertown more affordable than most cities in the US. When you rent an apartment in Chestertown, you can expect to pay about per month for a studio, $1,306 for a one-bedroom apartment, and around $1,460 for a two-bedroom apartment. If you opt for a three-bedroom rental, you could pay $1,906 or more.

Floor Plan Type
Average Rent
Average Sq Ft
One Bedroom
$1,306/month
754 Sq Ft
Two Bedroom
$1,460/month
998 Sq Ft
Three Bedroom
$1,906/month
0 Sq Ft
Floor Plan Type
Average Rent
Average Sq Ft
Floor Plan Type
Average Rent
Average Sq Ft
Floor Plan Type
Average Rent
Average Sq Ft

How much has average rent changed in Chestertown, MD?

In the past year, rent has increased by 2.7%, which averages out to $35 more per month.

Market Trends Over Time   The chart below compares average rent prices to the previous year during the same time period.
Last Updated September 2025
Legend
2024 2025
Market Trends Over Time
Rent Ranges in Chestertown, MD
Last Updated September 2025
$1,001 - $1,500
Most rental prices fall within this range
Rent Ranges in Chestertown, MD
Percentage*
Rent Range
0% Below $700/month
25% $700 - $1,000/month
75% $1,001 - $1,500/month
0% $1,501 - $2,000/month
0% Above $2,000/month

What salary do I need to live comfortably in Chestertown, MD?

Because the average rent in Chestertown is $1,306, you’ll want to make about $4,353 per month or $52,236 per year. The general guideline is to pay no more than 30 percent of your monthly income on rent. However, you’ll want to consider additional factors, such as your monthly bills and other expenses. Use our rent affordability calculator to help determine how much to budget for rent.

City

Chestertown, MD

27 Available Apartments for Rent

Search for Nearby Apartments

How does Chestertown, MD compare to other nearby cities and neighborhoods?

Use the tool below to compare Chestertown, MD to other nearby cities and neighborhoods. The Apartments.com neighborhood guides provide you with insight into the area’s transportation, things to do, and more.

Explore the Area Guide for Chestertown, MD

Apartment Averages

Nearby City Rent Trends

  • Centreville Average Rent
  • Edgewood Average Rent

Apartment communities in Chestertown we think you'll love

Kent Crossing Apartments

Kent Crossing Apartments

101 Morgnec Rd,
Chestertown, MD 21620

$1,300 - $2,000

1-3 Beds

866 Washington Ave

866 Washington Ave

866 Washington Ave,
Chestertown, MD 21620

$2,100

3 Beds

539 Round Top Rd

539 Round Top Rd

539 Round Top Rd,
Chestertown, MD 21620

$2,500

3 Beds

202 High St

202 High St

202 High St,
Chestertown, MD 21620

$2,500

2 Beds

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United States Maryland Chestertown Rental Trends

Methodology

† Our analysis of utilities, groceries, transportation, healthcare, home prices, and other goods and services is sourced from the Cost of Living Index, a respected benchmark published by the Council for Community and Economic Research (C2ER) that provides a thorough overview of living expenses across different regions.

Rent data is provided by CoStar Group’s Market Trend reports. As the industry leader in commercial real estate information, analytics, and news, CoStar conducts extensive research to produce and maintain a comprehensive database of commercial real estate information. We combine this data with public record to provide the most up-to-date rental information available.

Consumer goods, services, and home prices are sourced from the Cost of Living Index published by the Council for Community and Economic Research (C2ER). The data on this page is updated quarterly. It was last published in September 2025.

* Percentages may not total 100 due to rounding.

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Equal Housing Opportunity