Chestertown Homes For Sale $375,000 117 WATER STREET N #2A CHESTERTOWN, MD 2 Beds 1 Baths 787 Sqft $350,000 117 WATER STREET N #2B CHESTERTOWN, MD 7 Beds 6 Baths 850 Sqft $685,000 117 WATER STREET N #1A CHESTERTOWN, MD 3 Beds 3 Baths 3,000 Sqft $200,000 117 WATER STREET N #1B CHESTERTOWN, MD 1 Beds 1 Baths 700 Sqft $1,600,000 117 WATER STREET N 1A, 1B, 2A, & 2B CHESTERTOWN, MD 7 Beds 6 Baths 5,400 Sqft Open House $525,000 206 CAMELOT DRIVE CHESTERTOWN, MD 4 Beds 4 Baths 2,186 Sqft Open House $295,000 107 OAK LEAF DRIVE CHESTERTOWN, MD 3 Beds 2 Baths 1,947 Sqft $795,000 201 N LYNCHBURG STREET CHESTERTOWN, MD 0.1 Acres Coming Soon $440,000 104 GARLAND AVENUE CHESTERTOWN, MD 3 Beds 2 Baths 1,734 Sqft Coming Soon $315,000 154 LONGFELLOW DRIVE CHESTERTOWN, MD 3 Beds 1 Baths 1,408 Sqft $795,000 201 N LYNCHBURG STREET CHESTERTOWN, MD 2,045 Sqft $374,000 148 STEP ROAD CHESTERTOWN, MD 4 Beds 2 Baths 1,400 Sqft Active Under Contract $480,000 101 PINE TREE ROAD CHESTERTOWN, MD 4 Beds 2 Baths 1,848 Sqft Active Under Contract $675,000 118 LITTLE HARBOR WAY #201 CHESTERTOWN, MD 2 Beds 2 Baths 1,600 Sqft $695,000 118 LITTLE HARBOR WAY #202 CHESTERTOWN, MD 3 Beds 2 Baths 1,600 Sqft $612,000 204 DOUBLE CREEK ROAD CHESTERTOWN, MD 3 Beds 2 Baths 2,927 Sqft Pending $344,900 304 HADAWAY DRIVE CHESTERTOWN, MD 4 Beds 2 Baths 1,325 Sqft $189,900 132 PROSPECT STREET CHESTERTOWN, MD 2 Beds 1 Baths 910 Sqft $2,200 315 CANNON STREET CHESTERTOWN, MD 1,400 Sqft $249,500 112 METCALF ROAD CHESTERTOWN, MD 3 Beds 1 Baths 1,280 Sqft Pending $275,000 119 DARDEN ROAD CHESTERTOWN, MD 3 Beds 2 Baths 1,424 Sqft $2,300,000 200 HIGH STREET CHESTERTOWN, MD 6,918 Sqft Active Under Contract $143,000 9925 FLATLAND ROAD CHESTERTOWN, MD 3 Beds 1 Baths 1,368 Sqft Active Under Contract $449,000 105 PEARL CREEK LANE CHESTERTOWN, MD 3 Beds 2 Baths 1,961 Sqft View More