6,895

Chestertown, MD Homes

Section Image
    • 117 N Queen St, Chestertown, MD 21620
      117 N Queen St, Chestertown, MD 21620
      117 N Queen St, Chestertown, MD 21620
      /38

      Est $629,316 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,820 Sq Ft

      117 N Queen St, Chestertown, MD 21620

      117 N Queen St, Chestertown, MD 21620
    • 412 High St, Chestertown, MD 21620
      412 High St, Chestertown, MD 21620
      412 High St, Chestertown, MD 21620
      /45

      Est $471,579 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,867 Sq Ft

      412 High St, Chestertown, MD 21620

      412 High St, Chestertown, MD 21620
    • 529 Cannon St, Chestertown, MD 21620
      529 Cannon St, Chestertown, MD 21620
      529 Cannon St, Chestertown, MD 21620
      /30

      Est $360,046 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft

      529 Cannon St, Chestertown, MD 21620

      529 Cannon St, Chestertown, MD 21620
    • 25731 Collins Ave, Chestertown, MD 21620
      25731 Collins Ave, Chestertown, MD 21620
      25731 Collins Ave, Chestertown, MD 21620
      /53

      Est $854,823 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,751 Sq Ft

      25731 Collins Ave, Chestertown, MD 21620

      25731 Collins Ave, Chestertown, MD 21620
    • 703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      /31

      Est $265,532 Not Listed For Sale

      • 4 Beds
      • 1.5 Baths
      • 1,200 Sq Ft

      703 High St, Chestertown, MD 21620

      703 High St, Chestertown, MD 21620
    • 21095 Montana Ave, Chestertown, MD 21620
      21095 Montana Ave, Chestertown, MD 21620
      21095 Montana Ave, Chestertown, MD 21620
      /43

      Est $403,270 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,449 Sq Ft

      21095 Montana Ave, Chestertown, MD 21620

      21095 Montana Ave, Chestertown, MD 21620
    • 1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      /50

      Est $354,253 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft

      1006 Twin Ct, Chestertown, MD 21620

      1006 Twin Ct, Chestertown, MD 21620
    • 24025 Chestertown Rd, Chestertown, MD 21620
      24025 Chestertown Rd, Chestertown, MD 21620
      24025 Chestertown Rd, Chestertown, MD 21620
      /10

      Est $232,924 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,408 Sq Ft

      24025 Chestertown Rd, Chestertown, MD 21620

      24025 Chestertown Rd, Chestertown, MD 21620
    • 9762 Vogeler Dr, Chestertown, MD 21620
      9762 Vogeler Dr, Chestertown, MD 21620
      9762 Vogeler Dr, Chestertown, MD 21620
      /57

      Est $789,516 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,521 Sq Ft

      9762 Vogeler Dr, Chestertown, MD 21620

      9762 Vogeler Dr, Chestertown, MD 21620
    • 8983 Orchard Dr, Chestertown, MD 21620
      8983 Orchard Dr, Chestertown, MD 21620
      8983 Orchard Dr, Chestertown, MD 21620
      /22

      Est $527,528 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,084 Sq Ft

      8983 Orchard Dr, Chestertown, MD 21620

      8983 Orchard Dr, Chestertown, MD 21620
    • 8220 Airy Hill Rd, Chestertown, MD 21620
      8220 Airy Hill Rd, Chestertown, MD 21620
      8220 Airy Hill Rd, Chestertown, MD 21620
      /20

      Est $334,000 Not Listed For Sale

      8220 Airy Hill Rd, Chestertown, MD 21620

      8220 Airy Hill Rd, Chestertown, MD 21620
    • 104 Conley Dr, Chestertown, MD 21620
      104 Conley Dr, Chestertown, MD 21620
      104 Conley Dr, Chestertown, MD 21620
      /23

      Est $232,727 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,280 Sq Ft

      104 Conley Dr, Chestertown, MD 21620

      104 Conley Dr, Chestertown, MD 21620
    • 8880 Fairlee Rd, Chestertown, MD 21620
      8880 Fairlee Rd, Chestertown, MD 21620
      8880 Fairlee Rd, Chestertown, MD 21620
      /41

      Est $343,615 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 2,124 Sq Ft

      8880 Fairlee Rd, Chestertown, MD 21620

      8880 Fairlee Rd, Chestertown, MD 21620
    • 102 Conley Dr, Chestertown, MD 21620
      102 Conley Dr, Chestertown, MD 21620
      102 Conley Dr, Chestertown, MD 21620
      /6

      Est $233,634 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,280 Sq Ft

      102 Conley Dr, Chestertown, MD 21620

      102 Conley Dr, Chestertown, MD 21620
    • 24354 Langford Rd, Chestertown, MD 21620
      24354 Langford Rd, Chestertown, MD 21620
      24354 Langford Rd, Chestertown, MD 21620
      /49

      Est $656,544 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,266 Sq Ft

      24354 Langford Rd, Chestertown, MD 21620

      24354 Langford Rd, Chestertown, MD 21620
    • 6880 Pentridge Ln, Chestertown, MD 21620
      6880 Pentridge Ln, Chestertown, MD 21620
      6880 Pentridge Ln, Chestertown, MD 21620
      /85

      Est $1,888,236 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,931 Sq Ft

      6880 Pentridge Ln, Chestertown, MD 21620

      6880 Pentridge Ln, Chestertown, MD 21620
    • 7519 Quaker Neck Rd, Chestertown, MD 21620
      7519 Quaker Neck Rd, Chestertown, MD 21620
      7519 Quaker Neck Rd, Chestertown, MD 21620
      /19

      Est $240,624 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,136 Sq Ft

      7519 Quaker Neck Rd, Chestertown, MD 21620

      7519 Quaker Neck Rd, Chestertown, MD 21620
    • 7413 Poplar Ave, Chestertown, MD 21620
      7413 Poplar Ave, Chestertown, MD 21620
      7413 Poplar Ave, Chestertown, MD 21620
      /11

      Est $166,410 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 810 Sq Ft

      7413 Poplar Ave, Chestertown, MD 21620

      7413 Poplar Ave, Chestertown, MD 21620
    • 7448 Shortall St, Chestertown, MD 21620
      7448 Shortall St, Chestertown, MD 21620
      7448 Shortall St, Chestertown, MD 21620
      /20

      Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      7448 Shortall St, Chestertown, MD 21620

      7448 Shortall St, Chestertown, MD 21620
    • 24745 Langford Rd, Chestertown, MD 21620
      24745 Langford Rd, Chestertown, MD 21620
      24745 Langford Rd, Chestertown, MD 21620
      /13

      Est $330,132 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft

      24745 Langford Rd, Chestertown, MD 21620

      24745 Langford Rd, Chestertown, MD 21620
    • 6292 Broad Neck Rd, Chestertown, MD 21620
      6292 Broad Neck Rd, Chestertown, MD 21620
      6292 Broad Neck Rd, Chestertown, MD 21620
      /19

      Est $174,381 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,150 Sq Ft

      6292 Broad Neck Rd, Chestertown, MD 21620

      6292 Broad Neck Rd, Chestertown, MD 21620
    • 22770 Fairgale Farm Ln, Chestertown, MD 21620
      22770 Fairgale Farm Ln, Chestertown, MD 21620
      22770 Fairgale Farm Ln, Chestertown, MD 21620
      /68

      Est $1,200,457 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,535 Sq Ft

      22770 Fairgale Farm Ln, Chestertown, MD 21620

      22770 Fairgale Farm Ln, Chestertown, MD 21620
    • 24349 Chestertown Rd, Chestertown, MD 21620
      24349 Chestertown Rd, Chestertown, MD 21620
      24349 Chestertown Rd, Chestertown, MD 21620
      /32

      Est $327,980 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,327 Sq Ft

      24349 Chestertown Rd, Chestertown, MD 21620

      24349 Chestertown Rd, Chestertown, MD 21620
    • 22400 Great Oak Landing Rd, Chestertown, MD 21620
      22400 Great Oak Landing Rd, Chestertown, MD 21620
      22400 Great Oak Landing Rd, Chestertown, MD 21620
      /48

      Est $604,510 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,864 Sq Ft

      22400 Great Oak Landing Rd, Chestertown, MD 21620

      22400 Great Oak Landing Rd, Chestertown, MD 21620
    • 9096 Fairlee Rd, Chestertown, MD 21620
      9096 Fairlee Rd, Chestertown, MD 21620
      9096 Fairlee Rd, Chestertown, MD 21620
      /23

      Est $313,475 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,104 Sq Ft

      9096 Fairlee Rd, Chestertown, MD 21620

      9096 Fairlee Rd, Chestertown, MD 21620
    • 8899 Georgetown Rd, Chestertown, MD 21620
      8899 Georgetown Rd, Chestertown, MD 21620
      8899 Georgetown Rd, Chestertown, MD 21620
      /17

      Est $228,861 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 966 Sq Ft

      8899 Georgetown Rd, Chestertown, MD 21620

      8899 Georgetown Rd, Chestertown, MD 21620
    • 8559 Camp Rd, Chestertown, MD 21620
      8559 Camp Rd, Chestertown, MD 21620
      8559 Camp Rd, Chestertown, MD 21620
      /19

      Est $399,429 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,808 Sq Ft

      8559 Camp Rd, Chestertown, MD 21620

      8559 Camp Rd, Chestertown, MD 21620
    • 22532 Tolchester Beach Rd, Chestertown, MD 21620
      22532 Tolchester Beach Rd, Chestertown, MD 21620
      22532 Tolchester Beach Rd, Chestertown, MD 21620
      /8

      Est $192,000 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,696 Sq Ft

      22532 Tolchester Beach Rd, Chestertown, MD 21620

      22532 Tolchester Beach Rd, Chestertown, MD 21620
    • 9816 Fairlee Rd, Chestertown, MD 21620
      9816 Fairlee Rd, Chestertown, MD 21620
      9816 Fairlee Rd, Chestertown, MD 21620
      /34

      Est $501,382 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,624 Sq Ft

      9816 Fairlee Rd, Chestertown, MD 21620

      9816 Fairlee Rd, Chestertown, MD 21620
    • 10630 Club Rd, Chestertown, MD 21620
      10630 Club Rd, Chestertown, MD 21620
      10630 Club Rd, Chestertown, MD 21620
      /28

      Est $343,631 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,844 Sq Ft

      10630 Club Rd, Chestertown, MD 21620

      10630 Club Rd, Chestertown, MD 21620
    • 8970 Cumberland St, Chestertown, MD 21620
      8970 Cumberland St, Chestertown, MD 21620
      8970 Cumberland St, Chestertown, MD 21620
      /44

      Est $233,773 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft

      8970 Cumberland St, Chestertown, MD 21620

      8970 Cumberland St, Chestertown, MD 21620
    • 8900 Fairlee Rd, Chestertown, MD 21620
      8900 Fairlee Rd, Chestertown, MD 21620
      8900 Fairlee Rd, Chestertown, MD 21620
      /13

      Est $239,884 Not Listed For Sale

      • Studio
      • 2,188 Sq Ft

      8900 Fairlee Rd, Chestertown, MD 21620

      8900 Fairlee Rd, Chestertown, MD 21620
    • 23073 Parsons Rd, Chestertown, MD 21620
      23073 Parsons Rd, Chestertown, MD 21620
      23073 Parsons Rd, Chestertown, MD 21620
      /21

      Est $236,152 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft

      23073 Parsons Rd, Chestertown, MD 21620

      23073 Parsons Rd, Chestertown, MD 21620
    • 23087 Raleigh Rd, Chestertown, MD 21620
      23087 Raleigh Rd, Chestertown, MD 21620
      23087 Raleigh Rd, Chestertown, MD 21620
      /34

      Est $176,084 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 808 Sq Ft

      23087 Raleigh Rd, Chestertown, MD 21620

      23087 Raleigh Rd, Chestertown, MD 21620
    • 23081 Old Fairlee Rd, Chestertown, MD 21620
      23081 Old Fairlee Rd, Chestertown, MD 21620
      23081 Old Fairlee Rd, Chestertown, MD 21620
      /35

      Est $277,294 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,744 Sq Ft

      23081 Old Fairlee Rd, Chestertown, MD 21620

      23081 Old Fairlee Rd, Chestertown, MD 21620
    • 9220 N Bayview Ave, Chestertown, MD 21620
      9220 N Bayview Ave, Chestertown, MD 21620
      9220 N Bayview Ave, Chestertown, MD 21620
      /22

      Est $1,228,523 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,028 Sq Ft

      9220 N Bayview Ave, Chestertown, MD 21620

      9220 N Bayview Ave, Chestertown, MD 21620
    • 122 Island Lark Way, Chestertown, MD 21620
      122 Island Lark Way, Chestertown, MD 21620
      122 Island Lark Way, Chestertown, MD 21620
      /27

      Est $275,606 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft

      122 Island Lark Way, Chestertown, MD 21620

      122 Island Lark Way, Chestertown, MD 21620
    • 120 Island Lark Way, Chestertown, MD 21620
      120 Island Lark Way, Chestertown, MD 21620
      120 Island Lark Way, Chestertown, MD 21620
      /27

      Est $267,014 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft

      120 Island Lark Way, Chestertown, MD 21620

      120 Island Lark Way, Chestertown, MD 21620
    • 112 Island Lark Way, Chestertown, MD 21620
      112 Island Lark Way, Chestertown, MD 21620
      112 Island Lark Way, Chestertown, MD 21620
      /27

      Est $273,821 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft

      112 Island Lark Way, Chestertown, MD 21620

      112 Island Lark Way, Chestertown, MD 21620
    • 110 Island Lark Way, Chestertown, MD 21620
      110 Island Lark Way, Chestertown, MD 21620
      110 Island Lark Way, Chestertown, MD 21620
      /27

      Est $265,482 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,365 Sq Ft

      110 Island Lark Way, Chestertown, MD 21620

      110 Island Lark Way, Chestertown, MD 21620

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