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Chestertown, MD Houses for Rent

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  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
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    $2,500 Per Month

    • 4 Beds
    • 2 Baths
    • 1,476 Sq Ft
    • House for Rent

    1010 Twin Ct, Chestertown, MD 21620

    Cute 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic District. Eat in kitchen with back deck overlooking a beautiful yard that backs up to farm land that is preserved forever. Freshly painted and new carpet! Washer & dryer in unit. Extra storage in knee walls upstairs. $25 application fee per

    Jason Dey Kevin Dey Realty

    1010 Twin Ct, Chestertown, MD 21620
  • 128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    128 N Queen St Unit 3, Chestertown, MD 21620
    /10

    $1,450 Per Month

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    128 N Queen St Unit 3, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. 2nd floor private unit with spacious living area, seperate dining room, galley kitchen, full bathroom and bedroom. Unit is available immediately, utilities included: electric, water and sewer. Security

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • 104 Cedar St, Chestertown, MD 21620
    104 Cedar St, Chestertown, MD 21620
    104 Cedar St, Chestertown, MD 21620
    /15

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,612 Sq Ft
    • House for Rent

    104 Cedar St, Chestertown, MD 21620

    Great 3 Bedroom 2.5 Bath home located in Chestertown within close proximity of the college, downtown, and local shopping. The house will be available starting June 1st. There is a credit check, background check and rental application needed. No pets, no smoking. Excellent credit is required.

    Peter Heller Coldwell Banker Chesapeake Real Estate Company

    104 Cedar St, Chestertown, MD 21620
  • 104 Maple Ave Unit 6, Chestertown, MD 21620
    104 Maple Ave Unit 6, Chestertown, MD 21620
    104 Maple Ave Unit 6, Chestertown, MD 21620
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    $2,050 Per Month

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • House for Rent

    104 Maple Ave Unit 6, Chestertown, MD 21620

    Welcome to your new home in the heart of Chestertown Maryland, a charming historic town nestled along the Chester River, known for its vibrant arts scene, waterfront dining, and small-town charm. This beautifully designed property blends modern finishes with timeless appeal. Step inside to find engineered hardwood floors flowing throughout the main living areas, creating both warmth and

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 6, Chestertown, MD 21620
Maryland Kent County Chestertown

Houses for Rent in Chestertown, MD

Frequently Asked Questions

How much does it cost to rent a single-family home in Chestertown, MD?
The median rent for a single-family home in Chestertown, MD is $1,875 per month, though prices vary by neighborhood, size, and property type. As of June 2026, condos tend to be the most affordable option while townhouses and single-family homes are currently more expensive.
How much do you need to make to afford rent in Chestertown, MD?
To comfortably afford the median rent in Chestertown, MD, a household needs to earn roughly $77,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $1,925 per month in Chestertown, MD, renters typically need to show $5,775 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Chestertown, MD?
In Chestertown, MD, the price-to-rent ratio is 15.8, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Home Trends in Chestertown, MD

There are currently 4 single-family homes available for rent in Chestertown, MD. The median rent is $1,875 per month, with 3-bedroom houses renting at $2,500 and 4-bedroom houses at $2,225.

Rental Home Trends

Number of Houses for Rent
4
Median Single Family Home Rent
$1,875
Median 3 Bedroom Single Family Home Rent
$2,500
Median 4 Bedroom Single Family Home Rent
$2,225
How to Rent a Home

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