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Chestertown, MD Condos for Rent

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  • 24731 Langford Rd Unit B, Chestertown, MD 21620
    24731 Langford Rd Unit B, Chestertown, MD 21620
    24731 Langford Rd Unit B, Chestertown, MD 21620
    /8

    $1,200 Per Month

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

    24731 Langford Rd Unit B, Chestertown, MD 21620

    Property Id: 57147Private country apartment for rent on a creek, Kayaking fishing, Lots of wildlife to view. Grille available for use. Large bathroom and large kitchen. Shared laundry room. Recently painted and carpets professionally cleaned. All utilities included, fiber optic included

    (443) 282-2830

    24731 Langford Rd Unit B, Chestertown, MD 21620
  • 27318 Morgnec Rd Unit 27318 Unit B, Chestertown, MD 21620
    27318 Morgnec Rd Unit 27318 Unit B, Chestertown, MD 21620
    27318 Morgnec Rd Unit 27318 Unit B, Chestertown, MD 21620
    /16

    $1,700

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • Condo for Rent

    27318 Morgnec Rd Unit 27318 Unit B, Chestertown, MD 21620

    Recently updated 2 bedroom, 1 bathroom cottage available mid-July! Just 4 miles to downtown Chestertown but situated in a country setting. This cottage is part of a duplex. In addition to the 2 bedrooms there is a large loft on the third floor. Hardwood floors throughout with tile in the kitchen and bathroom. Original galley kitchen with 1940's farm sink, vintage style refrigerator, 18"

    27318 Morgnec Rd Unit 27318 Unit B, Chestertown, MD 21620
  • 7019 Church Hill Rd Unit B, Chestertown, MD 21620
    7019 Church Hill Rd Unit B, Chestertown, MD 21620
    7019 Church Hill Rd Unit B, Chestertown, MD 21620
    /25

    $1,200

    Total Monthly Price

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

    7019 Church Hill Rd Unit B, Chestertown, MD 21620

    7019 Church Hill Rd Unit B, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /11

    $1,300 Per Month

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

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, 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 entertaining.

    Amanda Morgan Brenton Realty Group

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

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 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.

Condo Rental Trends in Chestertown, MD

There are currently 5 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
5
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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