$2,000
Total Monthly Price
21324 Delaware Ave, Chestertown, MD 21620
House in the country (secluded) near Tolchester marina, 2 car attached garage, gas fireplace, one bedrm/bath first floor, 2 bedrms/bath second floor, small deck, 14 mins from Chestertown or Rock Hall, suitable for 3 people
Starting at $1,300 Per Month
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
$1,200 Per Month
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
$2,000 Per Month
102 Metcalf Rd, Chestertown, MD 21620
Property Id: 2613480This nearly new home built in 2023 has 3 bedrooms, 1.5 baths that is all electric with town water & sewer. Walking distance to 2 shopping centers, a YMCA and great restaurants. 1280 square feet of space to relax and entertain with friends and family. Want to save money each month, just ask for a longer lease! Pets will require a $400 non-refundable pet fee. If
(443) 282-2076
$1,200
Total Monthly Price
7019 Church Hill Rd Unit B, Chestertown, MD 21620
$2,400 Per Month
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
$1,450 Per Month
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
$2,600 Per Month
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. Small pets considered on a case to case basis. No smoking. Excellent credit is required.
Peter Heller Coldwell Banker Chesapeake Real Estate Company
$2,050 Per Month
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
$1,300 Per Month
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.
$1,800 Per Month
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
$1,400 Per Month
103 S Lynchburg St, Chestertown, MD 21620
This charming townhouse offers comfortable living in the heart of Chestertown. The main level features a roomy living space, an eat-in kitchen with a convenient half bath, and first-floor laundry. Upstairs, you'll find two bedrooms and a full bathroom. Enjoy the added bonus of one off-street parking spot. Move-in ready now. ***Tenants will be responsible for electric, town water and sewer, and
William Sutton Coldwell Banker Chesapeake Real Estate Company
$2,950 Per Month
222 Mount Vernon Ave, Chestertown, MD 21620
This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington College, just a short walk from downtown and the waterfront. Three finished levels and high ceilings plus bright, natural light make the home feel airy and spacious. Historic features include original heart-pine hardwood floors and beautiful molding throughout. The first floor includes an
Kellie Gough McLendon Long & Foster Real Estate, Inc.
Chestertown, Maryland, is a historic community on the Chester River, known for its maritime heritage and charming downtown. Founded in 1706, Chestertown was once a bustling port and remains a popular destination for homebuyers seeking a quieter lifestyle away from larger cities like Washington or Philadelphia. The town features a mix of Victorian homes downtown and waterfront properties, with river access being a significant draw. Residents enjoy boating on the river, and many homes feature private docks. The private Chester River Yacht & Country Club offers additional amenities such as an 18-hole golf course and a marina. Local parks like Wilmer Park provide walking trails and playgrounds, while the Wayne Gilchrest Trail caters to bikers and joggers. Downtown Chestertown is pedestrian-friendly, hosting boutiques, galleries and locally owned restaurants. Annual events like the Chestertown Tea Party Festival and the Sultana Downrigging Festival celebrate the town's rich history. Washington College, a small liberal arts institution, adds to the vibrant atmosphere. The University of Maryland Shore Medical Center provides health care services, including an emergency room. Chestertown is within driving distance of Baltimore, 75 miles away, and Baltimore/Washington International Airport. With its blend of historic charm, riverfront recreation and local amenities, Chestertown offers a unique living experience.
There are currently 13 homes available for rent in Chestertown, MD. The median rent is $2,050 per month, with single-family homes renting at $1,950, townhouses at $2,000 and condos at $1,550.
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Number of Homes for Rent
13
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Median Rent
$2,050
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Median Single Family Home Rent
$1,950
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Median Townhouse Rent
$2,000
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Median Condo Rent
$1,550
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