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Newest Homes for Rent in Chestertown, MD

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  • 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
    /9

    $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
    /27

    $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
  • 104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    104 Maple Ave Unit 3, Chestertown, MD 21620
    /26

    $1,520 Per Month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    104 Maple Ave Unit 3, 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 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 entertaining.

    Amanda Morgan Brenton Realty Group

    7501 Church Hill Rd Unit 5, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /23

    Starting at $1,300 Per Month

    • 1 - 3 Beds

    101 Morgnec Rd, Chestertown, MD 21620

    Quiet community, beautifully landscaped. Close to Washington College, can walk to downtown historic Chestertown and shops. A must see.

    Kent Crossing Apartments

    (443) 658-3052

    101 Morgnec Rd, 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
Maryland Kent County Chestertown

Newest Homes for Rent in Chestertown, MD

Frequently Asked Questions

How much does it cost to rent a home in Chestertown, MD?
The median rent for a home in Chestertown, MD is $1,925 per month, though prices vary by neighborhood, size, and property type. As of May 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 16.2, 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 7 homes available for rent in Chestertown, MD. The median rent is $1,925 per month, with single-family homes renting at $1,875, townhouses at $1,850 and condos at $1,800.

Rental Home Trends

Number of Homes for Rent
7
Median Rent
$1,925
Median Single Family Home Rent
$1,875
Median Townhouse Rent
$1,850
Median Condo Rent
$1,800
How to Rent a Home

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