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Newest Homes for Rent in Chestertown, MD

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  • 112 N Queen St Unit 4, Chestertown, MD 21620
    112 N Queen St Unit 4, Chestertown, MD 21620
    112 N Queen St Unit 4, Chestertown, MD 21620
    /4

    $1,250 Per Month

    • 1 Bed
    • 1 Bath
    • Condo for Rent

    112 N Queen St Unit 4, Chestertown, MD 21620

    Property Id: 2804546 Welcome to this charming 1 bedroom, 1 bathroom, 2nd floor unit. Located blocks from downtown Chestertown! Perfect for those looking for a cozy space to call their own. With amenities such as a dishwasher, refrigerator, washer, and dryer included, you'll have everything you need right at your fingertips. Criteria: Rent must be roughly 30% of tenant(s) monthly income

    112 N Queen St Unit 4, Chestertown, MD 21620
  • 206 N Mill St, Chestertown, MD 21620
    206 N Mill St, Chestertown, MD 21620
    206 N Mill St, Chestertown, MD 21620
    /13

    $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
  • 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
  • 109 Fairview Dr, Chestertown, MD 21620
    109 Fairview Dr, Chestertown, MD 21620
    109 Fairview Dr, Chestertown, MD 21620
    /10

    $1,750 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    109 Fairview Dr, Chestertown, MD 21620

    Property Id: 49100 Clean, updated 3 BR, 1 BA home in Chester Harbor. Nice yard, big screened porch, mud room/laundry room. QAC schools. No smoking, no pets, verifiable income required, good credit with no history of eviction, failure to pay rent, etc. First/last months' rent plus security deposit required for move in.

    109 Fairview Dr, Chestertown, MD 21620
  • 8890 Fairlee Rd, Chestertown, MD 21620
    8890 Fairlee Rd, Chestertown, MD 21620
    8890 Fairlee Rd, Chestertown, MD 21620
    /6

    $2,300 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
  • 1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    1010 Twin Ct, Chestertown, MD 21620
    /14

    $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
    /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, separate dining room, galley kitchen, full bathroom and bedroom. All with a fresh coat of paint! Unit is available immediately, utilities included in monthly

    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
  • 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

    101 Morgnec Rd, Chestertown, MD 21620
Maryland Kent County

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 $1,875 per month, though prices vary by neighborhood, size, and property type. As of August 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 $75,000 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 $1,875 per month in Chestertown, MD, renters typically need to show $5,625 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 Trends in Chestertown, MD

There are currently 10 homes available for rent in Chestertown, MD. The median rent is $1,875 per month, with single-family homes renting at $1,850, townhouses at $2,000 and condos at $1,800.

Rental Home Trends

Number of Homes for Rent
10
Median Rent
$1,875
Median Single Family Home Rent
$1,850
Median Townhouse Rent
$2,000
Median Condo Rent
$1,800
How to Rent a Home

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