6,867

Chestertown, MD Homes

Section Image
    • 703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      /31

      Est $245,274 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
    • 1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      /50

      Est $376,912 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
    • 23120 Club Terrace, Chestertown, MD 21620
      23120 Club Terrace, Chestertown, MD 21620
      23120 Club Terrace, Chestertown, MD 21620
      /41

      Est $412,638 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,789 Sq Ft

      23120 Club Terrace, Chestertown, MD 21620

      23120 Club Terrace, Chestertown, MD 21620
    • 9020 Cumberland St, Chestertown, MD 21620
      9020 Cumberland St, Chestertown, MD 21620
      9020 Cumberland St, Chestertown, MD 21620
      /48

      Est $268,392 Not Listed For Sale

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

      9020 Cumberland St, Chestertown, MD 21620

      9020 Cumberland St, Chestertown, MD 21620
    • 9762 Vogeler Dr, Chestertown, MD 21620
      9762 Vogeler Dr, Chestertown, MD 21620
      9762 Vogeler Dr, Chestertown, MD 21620
      /57

      Est $798,645 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 $519,921 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
    • 10589 Klamath Rd, Chestertown, MD 21620
      10589 Klamath Rd, Chestertown, MD 21620
      10589 Klamath Rd, Chestertown, MD 21620
      /33

      Est $309,703 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,326 Sq Ft

      10589 Klamath Rd, Chestertown, MD 21620

      10589 Klamath Rd, 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 $335,000 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 $259,935 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 $418,000 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
    • 6880 Pentridge Ln, Chestertown, MD 21620
      6880 Pentridge Ln, Chestertown, MD 21620
      6880 Pentridge Ln, Chestertown, MD 21620
      /85

      Est $1,914,258 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
    • 7671 Waterview Ln, Chestertown, MD 21620
      7671 Waterview Ln, Chestertown, MD 21620
      7671 Waterview Ln, Chestertown, MD 21620
      /13

      Est $404,131 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 2,153 Sq Ft

      7671 Waterview Ln, Chestertown, MD 21620

      7671 Waterview 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 $272,563 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 $178,322 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 810 Sq Ft

      7413 Poplar Ave, Chestertown, MD 21620

      7413 Poplar Ave, Chestertown, MD 21620
    • 6270 Quaker Neck Landing Rd, Chestertown, MD 21620
      6270 Quaker Neck Landing Rd, Chestertown, MD 21620
      6270 Quaker Neck Landing Rd, Chestertown, MD 21620
      /73

      Est $601,757 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,400 Sq Ft

      6270 Quaker Neck Landing Rd, Chestertown, MD 21620

      6270 Quaker Neck Landing Rd, Chestertown, MD 21620
    • 24745 Langford Rd, Chestertown, MD 21620
      24745 Langford Rd, Chestertown, MD 21620
      24745 Langford Rd, Chestertown, MD 21620
      /13

      Est $322,863 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 $229,279 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 $1,057,133 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
    • 22939 Bay Shore Rd, Chestertown, MD 21620
      22939 Bay Shore Rd, Chestertown, MD 21620
      22939 Bay Shore Rd, Chestertown, MD 21620
      /32

      Est $358,370 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,505 Sq Ft

      22939 Bay Shore Rd, Chestertown, MD 21620

      22939 Bay Shore Rd, Chestertown, MD 21620
    • 22956 Fairgale Farm Ln, Chestertown, MD 21620
      22956 Fairgale Farm Ln, Chestertown, MD 21620
      22956 Fairgale Farm Ln, Chestertown, MD 21620
      /82

      Est $1,282,903 Not Listed For Sale

      • 5 Beds
      • 4.5 Baths
      • 6,459 Sq Ft

      22956 Fairgale Farm Ln, Chestertown, MD 21620

      22956 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 $348,359 Not Listed For Sale

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

      24349 Chestertown Rd, Chestertown, MD 21620

      24349 Chestertown Rd, Chestertown, MD 21620
    • 8842 Fairlee Rd, Chestertown, MD 21620
      8842 Fairlee Rd, Chestertown, MD 21620
      8842 Fairlee Rd, Chestertown, MD 21620
      /13

      Est $247,381 Not Listed For Sale

      8842 Fairlee Rd, Chestertown, MD 21620

      8842 Fairlee 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 $659,876 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 $292,611 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 $257,096 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 $370,102 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 $489,772 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 $372,105 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 $271,776 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 $327,580 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 $261,709 Not Listed For Sale

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

      23073 Parsons Rd, Chestertown, MD 21620

      23073 Parsons Rd, Chestertown, MD 21620
    • 21199 Iowa Ave, Chestertown, MD 21620
      21199 Iowa Ave, Chestertown, MD 21620
      21199 Iowa Ave, Chestertown, MD 21620
      /29

      Est $272,534 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft

      21199 Iowa Ave, Chestertown, MD 21620

      21199 Iowa Ave, Chestertown, MD 21620
    • 8858 Georgetown Rd, Chestertown, MD 21620
      8858 Georgetown Rd, Chestertown, MD 21620
      8858 Georgetown Rd, Chestertown, MD 21620
      /15

      Est $334,674 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,300 Sq Ft

      8858 Georgetown Rd, Chestertown, MD 21620

      8858 Georgetown Rd, Chestertown, MD 21620
    • 23087 Raleigh Rd, Chestertown, MD 21620
      23087 Raleigh Rd, Chestertown, MD 21620
      23087 Raleigh Rd, Chestertown, MD 21620
      /34

      Est $175,077 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 808 Sq Ft

      23087 Raleigh Rd, Chestertown, MD 21620

      23087 Raleigh 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 $1,184,368 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
    • 24105 Chestertown Rd, Chestertown, MD 21620
      24105 Chestertown Rd, Chestertown, MD 21620
      24105 Chestertown Rd, Chestertown, MD 21620
      /17

      Est $310,313 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,317 Sq Ft

      24105 Chestertown Rd, Chestertown, MD 21620

      24105 Chestertown Rd, 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 $281,859 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 $279,637 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 $277,855 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

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