6,881

Chestertown, MD Homes

Section Image
    • 103 Flying Cloud Dr, Chestertown, MD 21620
      103 Flying Cloud Dr, Chestertown, MD 21620
      103 Flying Cloud Dr, Chestertown, MD 21620
      /28

      Est $331,759 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      103 Flying Cloud Dr, Chestertown, MD 21620

      103 Flying Cloud Dr, Chestertown, MD 21620
    • 107 Flying Cloud Dr, Chestertown, MD 21620
      107 Flying Cloud Dr, Chestertown, MD 21620
      107 Flying Cloud Dr, Chestertown, MD 21620
      /40

      Est $372,788 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      107 Flying Cloud Dr, Chestertown, MD 21620

      107 Flying Cloud Dr, Chestertown, MD 21620
    • 111 Flying Cloud Dr, Chestertown, MD 21620
      111 Flying Cloud Dr, Chestertown, MD 21620
      111 Flying Cloud Dr, Chestertown, MD 21620
      /40

      Est $372,520 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      111 Flying Cloud Dr, Chestertown, MD 21620

      111 Flying Cloud Dr, Chestertown, MD 21620
    • 113 Flying Cloud Dr, Chestertown, MD 21620
      113 Flying Cloud Dr, Chestertown, MD 21620
      113 Flying Cloud Dr, Chestertown, MD 21620
      /28

      Est $332,479 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      113 Flying Cloud Dr, Chestertown, MD 21620

      113 Flying Cloud Dr, Chestertown, MD 21620
    • 112 Flying Cloud Dr, Chestertown, MD 21620
      112 Flying Cloud Dr, Chestertown, MD 21620
      112 Flying Cloud Dr, Chestertown, MD 21620
      /42

      Est $346,032 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      112 Flying Cloud Dr, Chestertown, MD 21620

      112 Flying Cloud Dr, Chestertown, MD 21620
    • 108 Flying Cloud Dr, Chestertown, MD 21620
      108 Flying Cloud Dr, Chestertown, MD 21620
      108 Flying Cloud Dr, Chestertown, MD 21620
      /42

      Est $343,816 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,869 Sq Ft

      108 Flying Cloud Dr, Chestertown, MD 21620

      108 Flying Cloud Dr, Chestertown, MD 21620
    • 106 Flying Cloud Dr, Chestertown, MD 21620
      106 Flying Cloud Dr, Chestertown, MD 21620
      106 Flying Cloud Dr, Chestertown, MD 21620
      /42

      Est $344,561 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      106 Flying Cloud Dr, Chestertown, MD 21620

      106 Flying Cloud Dr, Chestertown, MD 21620
    • 104 Flying Cloud Dr, Chestertown, MD 21620
      104 Flying Cloud Dr, Chestertown, MD 21620
      104 Flying Cloud Dr, Chestertown, MD 21620
      /40

      Est $381,215 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      104 Flying Cloud Dr, Chestertown, MD 21620

      104 Flying Cloud Dr, Chestertown, MD 21620
    • 102 Flying Cloud Dr, Chestertown, MD 21620
      102 Flying Cloud Dr, Chestertown, MD 21620
      102 Flying Cloud Dr, Chestertown, MD 21620
      /28

      Est $336,152 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      102 Flying Cloud Dr, Chestertown, MD 21620

      102 Flying Cloud Dr, Chestertown, MD 21620
    • 100 Flying Cloud Dr, Chestertown, MD 21620
      100 Flying Cloud Dr, Chestertown, MD 21620
      100 Flying Cloud Dr, Chestertown, MD 21620
      /40

      Est $380,370 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      100 Flying Cloud Dr, Chestertown, MD 21620

      100 Flying Cloud Dr, Chestertown, MD 21620
    • 201 Silver Heel Rd, Chestertown, MD 21620
      201 Silver Heel Rd, Chestertown, MD 21620
      201 Silver Heel Rd, Chestertown, MD 21620
      /42

      Est $349,177 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      201 Silver Heel Rd, Chestertown, MD 21620

      201 Silver Heel Rd, Chestertown, MD 21620
    • 209 Silver Heel Rd, Chestertown, MD 21620
      209 Silver Heel Rd, Chestertown, MD 21620
      209 Silver Heel Rd, Chestertown, MD 21620
      /28

      Est $332,636 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      209 Silver Heel Rd, Chestertown, MD 21620

      209 Silver Heel Rd, Chestertown, MD 21620
    • 211 Silver Heel Rd, Chestertown, MD 21620
      211 Silver Heel Rd, Chestertown, MD 21620
      211 Silver Heel Rd, Chestertown, MD 21620
      /42

      Est $346,476 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      211 Silver Heel Rd, Chestertown, MD 21620

      211 Silver Heel Rd, Chestertown, MD 21620
    • 213 Silver Heel Rd, Chestertown, MD 21620
      213 Silver Heel Rd, Chestertown, MD 21620
      213 Silver Heel Rd, Chestertown, MD 21620
      /28

      Est $332,567 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      213 Silver Heel Rd, Chestertown, MD 21620

      213 Silver Heel Rd, Chestertown, MD 21620
    • 214 Silver Heel Rd, Chestertown, MD 21620
      214 Silver Heel Rd, Chestertown, MD 21620
      214 Silver Heel Rd, Chestertown, MD 21620
      /54

      Est $347,538 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,869 Sq Ft

      214 Silver Heel Rd, Chestertown, MD 21620

      214 Silver Heel Rd, Chestertown, MD 21620
    • 212 Silver Heel Rd, Chestertown, MD 21620
      212 Silver Heel Rd, Chestertown, MD 21620
      212 Silver Heel Rd, Chestertown, MD 21620
      /33

      Est $367,152 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      212 Silver Heel Rd, Chestertown, MD 21620

      212 Silver Heel Rd, Chestertown, MD 21620
    • 210 Silver Heel Rd, Chestertown, MD 21620
      210 Silver Heel Rd, Chestertown, MD 21620
      210 Silver Heel Rd, Chestertown, MD 21620
      /28

      Est $333,000 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      210 Silver Heel Rd, Chestertown, MD 21620

      210 Silver Heel Rd, Chestertown, MD 21620
    • 208 Silver Heel Rd, Chestertown, MD 21620
      208 Silver Heel Rd, Chestertown, MD 21620
      208 Silver Heel Rd, Chestertown, MD 21620
      /35

      Est $335,033 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      208 Silver Heel Rd, Chestertown, MD 21620

      208 Silver Heel Rd, Chestertown, MD 21620
    • 206 Silver Heel Rd, Chestertown, MD 21620
      206 Silver Heel Rd, Chestertown, MD 21620
      206 Silver Heel Rd, Chestertown, MD 21620
      /40

      Est $362,731 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      206 Silver Heel Rd, Chestertown, MD 21620

      206 Silver Heel Rd, Chestertown, MD 21620
    • 116 Silver Heel Rd, Chestertown, MD 21620
      116 Silver Heel Rd, Chestertown, MD 21620
      116 Silver Heel Rd, Chestertown, MD 21620
      /28

      Est $326,029 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,646 Sq Ft

      116 Silver Heel Rd, Chestertown, MD 21620

      116 Silver Heel Rd, Chestertown, MD 21620
    • 114 Silver Heel Rd, Chestertown, MD 21620
      114 Silver Heel Rd, Chestertown, MD 21620
      114 Silver Heel Rd, Chestertown, MD 21620
      /42

      Est $348,614 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      114 Silver Heel Rd, Chestertown, MD 21620

      114 Silver Heel Rd, Chestertown, MD 21620
    • 112 Silver Heel Rd, Chestertown, MD 21620
      112 Silver Heel Rd, Chestertown, MD 21620
      112 Silver Heel Rd, Chestertown, MD 21620
      /40

      Est $358,977 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      112 Silver Heel Rd, Chestertown, MD 21620

      112 Silver Heel Rd, Chestertown, MD 21620
    • 110 Silver Heel Rd, Chestertown, MD 21620
      110 Silver Heel Rd, Chestertown, MD 21620
      110 Silver Heel Rd, Chestertown, MD 21620
      /40

      Est $362,948 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,302 Sq Ft

      110 Silver Heel Rd, Chestertown, MD 21620

      110 Silver Heel Rd, Chestertown, MD 21620
    • 108 Silver Heel Rd, Chestertown, MD 21620
      108 Silver Heel Rd, Chestertown, MD 21620
      108 Silver Heel Rd, Chestertown, MD 21620
      /35

      Est $345,407 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,869 Sq Ft

      108 Silver Heel Rd, Chestertown, MD 21620

      108 Silver Heel Rd, Chestertown, MD 21620
    • 104 Silver Heel Rd, Chestertown, MD 21620
      104 Silver Heel Rd, Chestertown, MD 21620
      104 Silver Heel Rd, Chestertown, MD 21620
      /33

      Est $365,466 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,540 Sq Ft

      104 Silver Heel Rd, Chestertown, MD 21620

      104 Silver Heel Rd, Chestertown, MD 21620
    • 100 Silver Heel Rd, Chestertown, MD 21620
      100 Silver Heel Rd, Chestertown, MD 21620
      100 Silver Heel Rd, Chestertown, MD 21620
      /42

      Est $351,685 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,849 Sq Ft

      100 Silver Heel Rd, Chestertown, MD 21620

      100 Silver Heel Rd, Chestertown, MD 21620
    • 407 Calvert St, Chestertown, MD 21620
      407 Calvert St, Chestertown, MD 21620
      407 Calvert St, Chestertown, MD 21620
      /23

      Est $172,154 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,136 Sq Ft

      407 Calvert St, Chestertown, MD 21620

      407 Calvert St, Chestertown, MD 21620
    • 110 Elm St, Chestertown, MD 21620
      110 Elm St, Chestertown, MD 21620
      110 Elm St, Chestertown, MD 21620
      /20

      Est $358,400 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,267 Sq Ft

      110 Elm St, Chestertown, MD 21620

      110 Elm St, Chestertown, MD 21620
    • 511 High St, Chestertown, MD 21620
      511 High St, Chestertown, MD 21620
      511 High St, Chestertown, MD 21620
      /25

      Est $383,863 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,286 Sq Ft

      511 High St, Chestertown, MD 21620

      511 High St, Chestertown, MD 21620
    • 532 High St, Chestertown, MD 21620
      532 High St, Chestertown, MD 21620
      532 High St, Chestertown, MD 21620
      /29

      Est $306,703 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,186 Sq Ft

      532 High St, Chestertown, MD 21620

      532 High St, Chestertown, MD 21620
    • 118 N Queen St, Chestertown, MD 21620
      118 N Queen St, Chestertown, MD 21620
      118 N Queen St, Chestertown, MD 21620
      /57

      Est $607,388 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,202 Sq Ft

      118 N Queen St, Chestertown, MD 21620

      118 N Queen St, Chestertown, MD 21620
    • 526 N Kent St, Chestertown, MD 21620
      526 N Kent St, Chestertown, MD 21620
      526 N Kent St, Chestertown, MD 21620
      /50

      Est $482,324 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,120 Sq Ft

      526 N Kent St, Chestertown, MD 21620

      526 N Kent St, Chestertown, MD 21620
    • 106 S Queen St, Chestertown, MD 21620
      106 S Queen St, Chestertown, MD 21620
      106 S Queen St, Chestertown, MD 21620
      /40

      Est $809,049 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,296 Sq Ft

      106 S Queen St, Chestertown, MD 21620

      106 S Queen St, Chestertown, MD 21620
    • 214 Calvert St, Chestertown, MD 21620
      214 Calvert St, Chestertown, MD 21620
      214 Calvert St, Chestertown, MD 21620
      /24

      Est $240,780 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,408 Sq Ft

      214 Calvert St, Chestertown, MD 21620

      214 Calvert St, Chestertown, MD 21620
    • 835 High St, Chestertown, MD 21620
      835 High St, Chestertown, MD 21620
      835 High St, Chestertown, MD 21620
      /17

      Est $413,094 Not Listed For Sale

      • Studio
      • 2,848 Sq Ft

      835 High St, Chestertown, MD 21620

      835 High St, Chestertown, MD 21620
    • 213 Byford Dr, Chestertown, MD 21620
      213 Byford Dr, Chestertown, MD 21620
      213 Byford Dr, Chestertown, MD 21620
      /37

      Est $372,504 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 1,277 Sq Ft

      213 Byford Dr, Chestertown, MD 21620

      213 Byford Dr, Chestertown, MD 21620
    • 527 High St, Chestertown, MD 21620
      527 High St, Chestertown, MD 21620
      527 High St, Chestertown, MD 21620
      /33

      Est $351,950 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,124 Sq Ft

      527 High St, Chestertown, MD 21620

      527 High St, Chestertown, MD 21620
    • 410 Cannon St, Chestertown, MD 21620
      410 Cannon St, Chestertown, MD 21620
      410 Cannon St, Chestertown, MD 21620
      /23

      Est $283,904 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,584 Sq Ft

      410 Cannon St, Chestertown, MD 21620

      410 Cannon St, Chestertown, MD 21620
    • 101 School Rd, Chestertown, MD 21620
      101 School Rd, Chestertown, MD 21620
      101 School Rd, Chestertown, MD 21620
      /39

      Est $346,056 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,424 Sq Ft

      101 School Rd, Chestertown, MD 21620

      101 School Rd, Chestertown, MD 21620
    • 109 S College Ave, Chestertown, MD 21620
      109 S College Ave, Chestertown, MD 21620
      109 S College Ave, Chestertown, MD 21620
      /24

      Est $227,907 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,216 Sq Ft

      109 S College Ave, Chestertown, MD 21620

      109 S College Ave, Chestertown, MD 21620

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