Active 214 SILVER HEEL RD, CHESTERTOWN, MD 21620 - $350,000 Located in CHESTERTOWNBuilt in 2022MLS #: MDKE20064984 Bedrooms3 Baths1,972 SqFt More details Active 407 HIGH ST, CHESTERTOWN, MD 21620 - $828,000 Located in CHESTERTOWNBuilt in 1780MLS #: MDKE20064963 Bedrooms5 Baths3,047 SqFt More details Active 116 HARLAN LOOP, CHESTERTOWN, MD 21620 - $509,000 Located in CHESTERTOWNBuilt in 2009MLS #: MDKE20056105 Bedrooms4 Baths4,067 SqFt More details Active 101 COLEMAN DR, CHESTERTOWN, MD 21620 - $524,900 Located in CHESTERTOWNBuilt in 2001MLS #: MDQA20166243 Bedrooms3 Baths2,268 SqFt More details Active 103 TRAFFORD DR, CHESTERTOWN, MD 21620 - $419,900 Located in CHESTERTOWNBuilt in 2007MLS #: MDKE20064163 Bedrooms3 Baths1,944 SqFt More details Active 9816 FAIRLEE RD, CHESTERTOWN, MD 21620 - $535,000 Located in CHESTERTOWNBuilt in 1970MLS #: MDKE20064883 Bedrooms3 Baths1,624 SqFt More details Active 144 PROSPECT ST, CHESTERTOWN, MD 21620 - $179,000 Located in CHESTERTOWNBuilt in 1900MLS #: MDKE20064942 Bedrooms2 Baths1,082 SqFt More details Active 215 FAIRVIEW DR, CHESTERTOWN, MD 21620 - $425,000 Located in CHESTERTOWNBuilt in 2004MLS #: MDQA20170903 Bedrooms3 Baths1,784 SqFt More details Pending 118 LITTLE HARBOR WAY #202, CHESTERTOWN, MD 21620 - $675,000 Located in CHESTERTOWNBuilt in 2009MLS #: MDKE20058003 Bedrooms2 Baths1,600 SqFt More details Active 205 RIVER RD, CHESTERTOWN, MD 21620 - $920,000 Located in CHESTERTOWNBuilt in 2026MLS #: MDQA20165604 Bedrooms3 Baths2,877 SqFt More details Active 222 MOUNT VERNON AVE, CHESTERTOWN, MD 21620 - $434,999 Located in CHESTERTOWNBuilt in 1916MLS #: MDKE20058764 Bedrooms2 Baths1,656 SqFt More details Pending 21324 PERSIMMON DR, CHESTERTOWN, MD 21620 - $124,900 Located in CHESTERTOWNBuilt in 1955MLS #: MDKE20061782 Bedrooms1 Bath1,232 SqFt More details Active 103 METCALF RD, CHESTERTOWN, MD 21620 - $259,900 Located in CHESTERTOWNBuilt in 2025MLS #: MDKE20064463 Bedrooms2 Baths1,280 SqFt More details Active 208 CENTRAL DR, CHESTERTOWN, MD 21620 - $299,000 Located in CHESTERTOWNBuilt in 1978MLS #: MDQA20168363 Bedrooms1 Bath1,120 SqFt More details Active 103 LANDING LN, CHESTERTOWN, MD 21620 - $499,999 Located in CHESTERTOWNBuilt in 2015MLS #: MDKE20056702 Bedrooms3 Baths2,100 SqFt More details Active 7844 CHESTER CT, CHESTERTOWN, MD 21620 - $670,000 Located in CHESTERTOWNBuilt in 2005MLS #: MDKE20057964 Bedrooms3 Baths3,248 SqFt More details Active 226 S WATER ST, CHESTERTOWN, MD 21620 - $898,000 Located in CHESTERTOWNBuilt in 2025MLS #: MDKE20063543 Bedrooms4 Baths2,172 SqFt More details Active 201 N LYNCHBURG ST, CHESTERTOWN, MD 21620 - $750,000 Located in CHESTERTOWNBuilt in 1900MLS #: MDKE20061422 Baths2,045 SqFt More details Active 108 PINE ST, CHESTERTOWN, MD 21620 - $115,000 Located in CHESTERTOWNBuilt in 1957MLS #: MDKE20063223 Bedrooms1 Bath910 SqFt More details Pending 108 OAK LEAF DR, CHESTERTOWN, MD 21620 - $299,500 Located in CHESTERTOWNBuilt in 2004MLS #: MDKE20062242 Bedrooms3 Baths1,867 SqFt More details NextLast updated: 2026-05-09T11:00:25.624667Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.
