Active 107 METCALF RD, CHESTERTOWN, MD 21620 - $259,900 Located in CHESTERTOWNBuilt in 2025MLS #: MDKE20061863 Bedrooms2 Baths1,200 SqFt More details Active 21217 TEXAS AVE, CHESTERTOWN, MD 21620 - $265,000 Located in CHESTERTOWNBuilt in 1952MLS #: MDKE20063642 Bedrooms1 Bath912 SqFt More details Active 720 DEEP LANDING RD, CHESTERTOWN, MD 21620 - $369,999 Located in CHESTERTOWNBuilt in 2017MLS #: MDQA20167583 Bedrooms2 Baths1,271 SqFt More details Active 10087 JOHN CARVILL RD, CHESTERTOWN, MD 21620 - $695,000 Located in CHESTERTOWNBuilt in 1983MLS #: MDKE20063243 Bedrooms2 Baths1,566 SqFt More details Pending 104 GARLAND AVE, CHESTERTOWN, MD 21620 - $440,000 Located in CHESTERTOWNBuilt in 2005MLS #: MDQA20162643 Bedrooms2 Baths1,734 SqFt More details Active 113 PEAR TREE POINT RD, CHESTERTOWN, MD 21620 - $250,000 Located in CHESTERTOWNBuilt in 1973MLS #: MDQA20164783 Bedrooms1 Bath1,296 SqFt More details Active 2032 PONDTOWN RD, CHESTERTOWN, MD 21620 - $325,000 Located in CHESTERTOWNBuilt in 2007MLS #: MDQA20166883 Bedrooms2 Baths1,120 SqFt More details Active 109 METCALF RD, CHESTERTOWN, MD 21620 - $264,900 Located in CHESTERTOWNBuilt in 2025MLS #: MDKE20059683 Bedrooms2 Baths1,280 SqFt More details Active 154 LONGFELLOW DR, CHESTERTOWN, MD 21620 - $299,000 Located in CHESTERTOWNBuilt in 1975MLS #: MDQA20162503 Bedrooms1 Bath1,408 SqFt More details Active 7844 CHESTER CT, CHESTERTOWN, MD 21620 - $695,000 Located in CHESTERTOWNBuilt in 2005MLS #: MDKE20057964 Bedrooms3 Baths3,248 SqFt More details Pending 206 CAMELOT DR, CHESTERTOWN, MD 21620 - $499,000 Located in CHESTERTOWNBuilt in 2009MLS #: MDKE20061244 Bedrooms4 Baths2,186 SqFt More details Active 218 CAMELOT DR, CHESTERTOWN, MD 21620 - $525,000 Located in CHESTERTOWNBuilt in 2010MLS #: MDKE20059825 Bedrooms4 Baths3,932 SqFt More details Active 222 MOUNT VERNON AVE, CHESTERTOWN, MD 21620 - $439,999 Located in CHESTERTOWNBuilt in 1916MLS #: MDKE20058764 Bedrooms2 Baths1,656 SqFt More details Pending 108 PINE ST, CHESTERTOWN, MD 21620 - $115,000 Located in CHESTERTOWNBuilt in 1957MLS #: MDKE20063223 Bedrooms1 Bath910 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 132 PROSPECT ST, CHESTERTOWN, MD 21620 - $157,400 Located in CHESTERTOWNBuilt in 1949MLS #: MDKE20061102 Bedrooms1 Bath910 SqFt More details Active 8276 BROAD NECK RD, CHESTERTOWN, MD 21620 - $1,495,000 Located in CHESTERTOWNBuilt in 1991MLS #: MDKE20062164 Bedrooms4 Baths3,383 SqFt More details Active 109 S COLLEGE AVE, CHESTERTOWN, MD 21620 - $419,900 Located in CHESTERTOWNBuilt in 1900MLS #: MDKE20060403 Bedrooms3 Baths1,216 SqFt More details Active 21125 IOWA AVE, CHESTERTOWN, MD 21620 - $339,900 Located in CHESTERTOWNBuilt in 1962MLS #: MDKE20061982 Bedrooms1 Bath1,294 SqFt More details Active 704 TRUSLOW RD, CHESTERTOWN, MD 21620 - $440,000 Located in CHESTERTOWNBuilt in 1992MLS #: MDQA20166323 Bedrooms3 Baths2,060 SqFt More details NextLast updated: 2026-04-11T04:00:25.154331Z. Listing information is provided by Bright MLS. Listings are generated from various brokers who participate in IDX. Information is deemed reliable but not guaranteed.
