Address	Bed / Bath	Listing Price
311 DEVON DRIVE 311 Devon Drive is located in Coventry Farms; and being located within the Chestertown town limits offers town utilities. The front entrance welcomes you with an open two-story foyer to the second-floor balcony. To the left of the front foyer is a den and to the right is a formal dining room. The CHESTERTOWN, MD Living Area: 3504 Sqft.	5 Beds, 4 Baths	$598,000
112 SILVER HEEL DRIVE Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area, and bright, well-appointed kitchen. This level al CHESTERTOWN, MD Living Area: 2615 Sqft.	5 Beds, 4 Baths	$369,900
304 HADAWAY DRIVE Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom ti CHESTERTOWN, MD Living Area: 1325 Sqft.	4 Beds, 2 Baths	$425,000
318 LINCOLN Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The CHESTERTOWN, MD Living Area: 960 Sqft.	3 Beds, 2 Baths	$269,000
107 MALONE AVENUE Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms ha CHESTERTOWN, MD Living Area: 1200 Sqft.	3 Beds, 1 Bath	$290,000
100 ADELA WAY Days on Market Reporting Incorrectly- Property listed Oct 30, 2025 Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover woo CHESTERTOWN, MD Living Area: 3799 Sqft.	4 Beds, 4 Baths	$515,000
116 HARLAN LOOP $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square f CHESTERTOWN, MD Living Area: 4067 Sqft.	5 Beds, 4 Baths	$519,000
907 N MEADOWVIEW DRIVE JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space. Step inside to find a CHESTERTOWN, MD Living Area: 1842 Sqft.	3 Beds, 3 Baths	$410,000
251 DEVON DRIVE NO HOA OR FRONT FEES: Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to th CHESTERTOWN, MD Living Area: 3935 Sqft.	3 Beds, 3 Baths	$595,000
141 PROSPECT STREET INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find! Located just minutes from Chestertown and Wa CHESTERTOWN, MD Living Area: 1156 Sqft.	4 Beds, 2 Baths	$167,000
132 PROSPECT STREET Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sol CHESTERTOWN, MD Living Area: 910 Sqft.	2 Beds, 1 Bath	$62,400
624 HIGH STREET Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shop CHESTERTOWN, MD Living Area: 1290 Sqft.	2 Beds, 1 Bath	$240,000

Chestertown, Maryland, United States

Homes for sale near WCTR-AM (Chestertown), Chestertown, MD, USA