6,870

Chestertown, MD Homes

Section Image
    • 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
    • 110 Island Lark Way, Chestertown, MD 21620
      110 Island Lark Way, Chestertown, MD 21620
      110 Island Lark Way, Chestertown, MD 21620
      /27

      Est $277,984 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
    • 108 Island Lark Way, Chestertown, MD 21620
      108 Island Lark Way, Chestertown, MD 21620
      108 Island Lark Way, Chestertown, MD 21620
      /27

      Est $287,152 Not Listed For Sale

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

      108 Island Lark Way, Chestertown, MD 21620

      108 Island Lark Way, Chestertown, MD 21620
    • 103 Flying Cloud Dr, Chestertown, MD 21620
      103 Flying Cloud Dr, Chestertown, MD 21620
      103 Flying Cloud Dr, Chestertown, MD 21620
      /28

      Est $341,963 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 $390,807 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 $390,918 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 $344,331 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 $351,818 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
    • 106 Flying Cloud Dr, Chestertown, MD 21620
      106 Flying Cloud Dr, Chestertown, MD 21620
      106 Flying Cloud Dr, Chestertown, MD 21620
      /42

      Est $351,325 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 $388,048 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 $348,255 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 $388,217 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 $356,295 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 $343,479 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 $354,097 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 $343,028 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 $344,420 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 $372,554 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 $333,658 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 $343,698 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 $371,835 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 $336,494 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 $352,168 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 $379,245 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 $374,386 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 $351,783 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 $371,707 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 $354,158 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 $175,014 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
    • 207 Pondview Ct, Chestertown, MD 21620
      207 Pondview Ct, Chestertown, MD 21620
      207 Pondview Ct, Chestertown, MD 21620
      /57

      Est $576,748 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 2,878 Sq Ft

      207 Pondview Ct, Chestertown, MD 21620

      207 Pondview Ct, Chestertown, MD 21620
    • 807 S Meadowview Dr, Chestertown, MD 21620
      807 S Meadowview Dr, Chestertown, MD 21620
      807 S Meadowview Dr, Chestertown, MD 21620
      /22

      Est $494,424 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,464 Sq Ft

      807 S Meadowview Dr, Chestertown, MD 21620

      807 S Meadowview Dr, Chestertown, MD 21620
    • 8757 Orchard Dr, Chestertown, MD 21620
      8757 Orchard Dr, Chestertown, MD 21620
      8757 Orchard Dr, Chestertown, MD 21620
      /49

      Est $515,662 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 2,210 Sq Ft

      8757 Orchard Dr, Chestertown, MD 21620

      8757 Orchard Dr, Chestertown, MD 21620
    • 511 High St, Chestertown, MD 21620
      511 High St, Chestertown, MD 21620
      511 High St, Chestertown, MD 21620
      /25

      Est $381,580 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 $310,992 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 $647,283 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
    • 129 Manor Ave, Chestertown, MD 21620
      129 Manor Ave, Chestertown, MD 21620
      129 Manor Ave, Chestertown, MD 21620
      /32

      Est $272,510 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 960 Sq Ft

      129 Manor Ave, Chestertown, MD 21620

      129 Manor Ave, 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 $495,655 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
    • 214 Calvert St, Chestertown, MD 21620
      214 Calvert St, Chestertown, MD 21620
      214 Calvert St, Chestertown, MD 21620
      /24

      Est $267,212 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

      Not Listed For Sale

      • Studio
      • 2,848 Sq Ft

      835 High St, Chestertown, MD 21620

      835 High St, Chestertown, MD 21620
    • 211 Byford Dr, Chestertown, MD 21620
      211 Byford Dr, Chestertown, MD 21620
      211 Byford Dr, Chestertown, MD 21620
      /31

      Est $412,886 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,616 Sq Ft

      211 Byford Dr, Chestertown, MD 21620

      211 Byford Dr, Chestertown, MD 21620

Showing Results 561 - 600, Page 15 of 18

Maryland Kent County Chestertown

Real Estate & Homes

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group