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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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    $2,100 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
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    $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. Utilities included!!!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, separate dining room, galley kitchen, full bathroom and bedroom. All with a fresh coat of paint! Unit is available immediately,

    Amanda Morgan Brenton Realty Group

    128 N Queen St Unit 3, Chestertown, MD 21620
  • 206 N Mill St, Chestertown, MD 21620
    206 N Mill St, Chestertown, MD 21620
    206 N Mill St, Chestertown, MD 21620
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    $1,950 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,520 Sq Ft
    • House for Rent

    206 N Mill St, Chestertown, MD 21620

    Entire historic home in downtown Chestertown for a great price!! One block from shops, restaurants, galleries and much more. Large living room opens to eat-in kitchen with beautiful countertops and all stainless steel appliances. Half bath and laundry on main floor and 3 bedrooms and two full bathrooms upstairs. Hardwood floors throughout. Private backyard with fence and storage shed. Dead end

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    206 N Mill St, Chestertown, MD 21620
Maryland Kent County

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 $1,795 per month, though prices vary by neighborhood, size, and property type. As of September 2026, condos tend to be the most affordable option while single-family homes and townhouses 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 $71,800 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 $1,795 per month in Chestertown, MD, renters typically need to show $5,385 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 17.1, 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 3 single-family homes available for rent in Chestertown, MD. The median rent is $1,795 per month, with 3-bedroom houses renting at $2,500.

Rental Home Trends

Number of Houses for Rent
3
Median Single Family Home Rent
$1,795
Median 3 Bedroom Single Family Home Rent
$2,500
How to Rent a Home

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