Active 110 TRAFFORD DR, CHESTERTOWN, MD 21620 - $450,000 Located in CHESTERTOWNBuilt in 2007MLS #: MDKE2005964 4 Bedrooms3 Baths 2,880 SqFt More details Active 103 METCALF RD, CHESTERTOWN, MD 21620 - $259,900 Located in CHESTERTOWNBuilt in 2025MLS #: MDKE2006446 3 Bedrooms2 Baths 1,280 SqFt More details Active 104 CONLEY DR, CHESTERTOWN, MD 21620 - $247,000 Located in CHESTERTOWNBuilt in 1979MLS #: MDKE2006686 3 Bedrooms2 Baths 1,280 SqFt More details Active 522 HIGH ST, CHESTERTOWN, MD 21620 - $425,000 Located in CHESTERTOWNBuilt in 1820MLS #: MDKE2006614 2 Bedrooms3 Baths 1,518 SqFt More details Pending 10584 KLAMATH RD, CHESTERTOWN, MD 21620 - $319,900 Located in CHESTERTOWNCHESAPEAKE LANDING MLS #: MDKE2006328 3 Bedrooms2 Baths KENT County More details Active 201 RIVER RD, CHESTERTOWN, MD 21620 - $629,900 Located in CHESTERTOWNBuilt in 1977MLS #: MDQA2017684 3 Bedrooms2 Baths 2,430 SqFt More details Active 104 ACORN DR, CHESTERTOWN, MD 21620 - $284,900 Located in CHESTERTOWNBuilt in 2004MLS #: MDKE2006668 3 Bedrooms3 Baths 1,900 SqFt More details Active 102 FLYING CLOUD DR, CHESTERTOWN, MD 21620 - $329,900 Located in CHESTERTOWNBuilt in 2023MLS #: MDKE2006586 3 Bedrooms3 Baths 1,896 SqFt More details Active 517 ROUND TOP RD, CHESTERTOWN, MD 21620 - $349,900 Located in CHESTERTOWNBuilt in 1960MLS #: MDQA2017680 3 Bedrooms1 Bath 1,248 SqFt More details Active 101 S MILL ST, CHESTERTOWN, MD 21620 - $515,000 Located in CHESTERTOWNBuilt in 1900MLS #: MDKE2006674 2 Bedrooms3 Baths 1,476 SqFt More details Active 103 S LYNCHBURG ST, CHESTERTOWN, MD 21620 - $1,400 Located in CHESTERTOWNBuilt in 1980MLS #: MDKE2006688 2 Bedrooms2 Baths 1,040 SqFt More details Pending 1014 TWIN CT, CHESTERTOWN, MD 21620 - $499,000 Located in CHESTERTOWNBuilt in 2017MLS #: MDKE2006516 3 Bedrooms2 Baths 1,817 SqFt More details Pending 114 CHESTER VW, CHESTERTOWN, MD 21620 - $1,650,000 Located in CHESTERTOWNBuilt in 1960MLS #: MDQA2017518 3 Bedrooms2 Baths 2,064 SqFt More details Active 110 PROSPECT ST, CHESTERTOWN, MD 21620 - $119,895 Located in CHESTERTOWNBuilt in 1900MLS #: MDKE2006626 3 Bedrooms2 Baths 2,210 SqFt More details Active 234 N COLLEGE AVE, CHESTERTOWN, MD 21620 - $100,000 Located in CHESTERTOWNBuilt in 1900MLS #: MDKE2006670 2 Bedrooms1 Bath 1,296 SqFt More details Pending 231 RICHARD DR, CHESTERTOWN, MD 21620 - $1,150,000 Located in CHESTERTOWNBuilt in 1981MLS #: MDKE2005900 5 Bedrooms3 Baths 2,956 SqFt More details Active 103 TRAFFORD DR, CHESTERTOWN, MD 21620 - $399,900 Located in CHESTERTOWNBuilt in 2007MLS #: MDKE2006416 3 Bedrooms3 Baths 1,944 SqFt More details Active 240 MERGANSER DR, CHESTERTOWN, MD 21620 - $389,000 Located in CHESTERTOWNBuilt in 2024MLS #: MDQA2016900 3 Bedrooms2 Baths 1,120 SqFt More details Active 202 ROYSTON SHORES RD, CHESTERTOWN, MD 21620 - $1,200,000 Located in CHESTERTOWNBuilt in 1968MLS #: MDQA2017462 4 Bedrooms3 Baths 2,292 SqFt More details Active 8276 BROAD NECK RD, CHESTERTOWN, MD 21620 - $1,495,000 Located in CHESTERTOWNBuilt in 1991MLS #: MDKE2006216 4 Bedrooms4 Baths 3,383 SqFt More details Next Last updated: 2026-06-23T18:31:02.361011Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.
