Browse All Chestertown MD Townhouse Listings for Sale

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitch...

3 Beds
2 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

107 Conley Dr, Chestertown $240,000

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable locatio...

3 Beds
1 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

121 Metcalf Rd, Chestertown $264,900

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

3 Beds
2 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

21324 Persimmon Dr, Chestertown $199,000

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, thi...

2 Beds
1 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

409 Calvert St, Chestertown $155,000

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants...

3 Beds
2 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

104 Conley Dr, Chestertown $239,900 ▼

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, lo...

3 Beds
2 Baths

Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact: 4108230033

101 S Mill St, Chestertown $515,000

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District...

2 Beds
3 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

104 Acorn Dr, Chestertown $275,000 ▼

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly posi...

3 Beds
3 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

103 Metcalf Rd, Chestertown $259,900

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

3 Beds
2 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442

226 S Water St, Chestertown $898,000

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner ...

3 Beds
4 Baths

Courtesy of Gunther-McClary Real Estate