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Chestertown, MD Condos for Rent

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  • 200 Cannon St Unit 1A, Chestertown, MD 21620
    200 Cannon St Unit 1A, Chestertown, MD 21620
    200 Cannon St Unit 1A, Chestertown, MD 21620
    /20

    $1,300

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 580 Sq Ft
    • Condo for Rent

    200 Cannon St Unit 1A, Chestertown, MD 21620

    Ground floor apartment in nice, safe, quiet, upscale area 2 blocks from river and waterfront park, 1 block from downtown (in Historic District). Suitable for 1 person. No pets or smoking.

    200 Cannon St Unit 1A, Chestertown, MD 21620
  • 104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    /7

    $1,495 Per Month

    • 2 Beds
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    104 Maple Ave Unit 3, Chestertown, MD 21620

    Nick Dively Real Broker, LLC - Annapolis

    104 Maple Ave Unit 3, Chestertown, MD 21620
  • 7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
    /17

    $1,800 Per Month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620

    If you’ve been searching for an open‑concept apartment with a stunning view, your search ends here. This fully renovated third‑floor residence delivers modern style, thoughtful updates, and an airy layout that feels instantly welcoming.Step into a beautifully redesigned kitchen featuring ample cabinetry, upgraded appliances, and a spacious island perfect for cooking, gathering, or

    Amanda Morgan Brenton Realty Group

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
Maryland Kent County

Condos for Rent in Chestertown, MD

Frequently Asked Questions

How much does it cost to rent a condo in Chestertown, MD?
The median rent for a condo in Chestertown, MD is $1,550 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 $59,800 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 $1,495 per month in Chestertown, MD, renters typically need to show $4,485 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 20.8, 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.

Condo Rental Trends in Chestertown, MD

There are currently 3 condos available for rent in Chestertown, MD. The median rent is $1,550 per month, with 1-bedroom condos renting at $1,300 and 2-bedroom condos at $1,800.

Rental Home Trends

Number of Condos for Rent
3
Median Condo Rent
$1,550
Median 1 Bedroom Condo Rent
$1,300
Median 2 Bedroom Condo Rent
$1,800
How to Rent a Home

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