7

Chestertown, MD Houses for Rent

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  • 129a Manor Ave N, Chestertown, MD 21620
    129a Manor Ave N, Chestertown, MD 21620
    129a Manor Ave N, Chestertown, MD 21620
    /12

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • House for Rent

    129a Manor Ave N, Chestertown, MD 21620

    Property Id: 1589400 **PLEASE CONFIRM PROPERTY IS AVAILABLE BEFORE APPLYING** 129A Manor Ave, Chestertown, MD. This charming 3-bedroom, 2-bath home is move-in ready with a brand new HVAC system for year-round comfort. The spacious interior offers a welcoming living space, while the detached 1-bay garage provides the perfect spot for storage or a workshop. Located in a convenient area,

    129a Manor Ave N, Chestertown, MD 21620
  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    /14

    $2,400 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 Maple Ave Unit 6, Chestertown, MD 21620
    104 Maple Ave Unit 6, Chestertown, MD 21620
    104 Maple Ave Unit 6, Chestertown, MD 21620
    /27

    $1,920 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
  • 2201 Pondtown Rd, Chestertown, MD 21620
    2201 Pondtown Rd, Chestertown, MD 21620
    2201 Pondtown Rd, Chestertown, MD 21620
    /24

    $1,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,272 Sq Ft
    • House for Rent

    2201 Pondtown Rd, Chestertown, MD 21620

    Open House Sunday 7/26 10-11AM, 7/27 Monday 2-3PMEnjoy peaceful country living with convenient access to Route 301 in this 3-bedroom, 1-bath rancher situated on a spacious 1-acre lot in Pondtown. Inside, you'll find fresh new carpeting throughout, a generous living room featuring a decorative fireplace (non-operational), a separate dining room, and a large kitchen with plenty of room for

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    2201 Pondtown Rd, Chestertown, MD 21620
  • 104 Maple Ave Unit 4, Chestertown, MD 21620
    104 Maple Ave Unit 4, Chestertown, MD 21620
    104 Maple Ave Unit 4, Chestertown, MD 21620
    /12

    $1,820 Per Month

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

    104 Maple Ave Unit 4, 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 4, Chestertown, MD 21620
  • 8890 Fairlee Rd, Chestertown, MD 21620
    8890 Fairlee Rd, Chestertown, MD 21620
    8890 Fairlee Rd, Chestertown, MD 21620
    /6

    $2,500 Per Month

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • House for Rent

    8890 Fairlee Rd, Chestertown, MD 21620

    Beautiful and clean ranch featuring open floor plan and separated primary bedroom. Adorable kitchen and dining area with slider to rear deck. laundry included

    Darlene Winegardner RE/MAX Executive

    8890 Fairlee Rd, 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 $1,910 per month, though prices vary by neighborhood, size, and property type. As of July 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 $76,800 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 $1,920 per month in Chestertown, MD, renters typically need to show $5,760 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 15.7, 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 single-family homes available for rent in Chestertown, MD. The median rent is $1,910 per month, with 3-bedroom houses renting at $2,500.

Rental Home Trends

Number of Houses for Rent
7
Median Single Family Home Rent
$1,910
Median 3 Bedroom Single Family Home Rent
$2,500
How to Rent a Home

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