Chestertown, Maryland

Homes for Sale

+1(888) 897-9225
Newest Listings
  1. New

    $824,900

    • 5 bed
    • 4 bath
    • 4353 SqFt
    8999 ORCHARD DR
    Orchard Hill
    Coldwell Banker Chesapeake Real Estate Company

    4 days on neighborhoods.com

  2. $259,900

    • 3 bed
    • 2 bath
    • 1280 SqFt
    115 METCALF RD
    Real Broker, LLC - Chester

    6 days on neighborhoods.com

  3. $325,000

    • 4 bed
    • 2 bath
    • 2198 SqFt
    200 MANOR AVE
    TTR Sotheby's International Realty

    9 days on neighborhoods.com

  4. $264,900

    • 3 bed
    • 2 bath
    121 METCALF RD
    Real Broker, LLC - Chester

    13 days on neighborhoods.com

  5. $199,000

    • 2 bed
    • 1 bath
    • 1232 SqFt
    21324 PERSIMMON DR
    Benson & Mangold, LLC

    16 days on neighborhoods.com

  6. $335,000

    • 3 bed
    • 2 bath
    • 1412 SqFt
    10720 FORESTON RD
    Compass

    17 days on neighborhoods.com

  7. $155,000

    • 3 bed
    • 2 bath
    • 1192 SqFt
    409 CALVERT ST
    Historic Chestertown
    Chesapeake Real Estate Associates, LLC

    19 days on neighborhoods.com

  8. $885,000

    • 5 bed
    • 4 bath
    • 2639 SqFt
    7680 COUNTRY CLUB LN
    Gunther-McClary Real Estate

    23 days on neighborhoods.com

  9. $344,000

    • 3 bed
    • 2 bath
    • 1216 SqFt
    9126 FAIRLEE RD
    Chesapeake Real Estate Associates, LLC

    26 days on neighborhoods.com

  10. $325,000

    • 3 bed
    • 1 bath
    • 1000 SqFt
    896 WASHINGTON AVE
    Coldwell Banker Chesapeake Real Estate Company

    1 month on neighborhoods.com

  11. $299,900

    • 3 bed
    • 1 bath
    • 1248 SqFt
    517 ROUND TOP RD
    Keller Williams Flagship

    1 month on neighborhoods.com

  12. $239,900

    • 3 bed
    • 2 bath
    • 1280 SqFt
    104 CONLEY DR
    Chester Arms
    Cummings & Co. Realtors

    1 month on neighborhoods.com

  13. $90,000

    • 2 bed
    • 1 bath
    • 1296 SqFt
    234 N COLLEGE AVE
    Cummings & Co Realtors

    1 month on neighborhoods.com

  14. $275,000

    • 3 bed
    • 3 bath
    • 1900 SqFt
    104 ACORN DR
    Cross Street Realtors LLC

    1 month on neighborhoods.com

  15. $468,000

    • 3 bed
    • 2 bath
    • 3262 SqFt
    25750 COLLINS AVE
    Country Club Estates
    Doug Ashley Realtors, LLC

    1 month on neighborhoods.com

  16. $69,900

    • 3 bed
    • 2 bath
    • 2210 SqFt
    110 PROSPECT ST
    ANR Realty, LLC

    1 month on neighborhoods.com

  17. $429,900

    • 4 bed
    • 3 bath
    • 2160 SqFt
    10781 FERMOY RD
    Chesapeake Landing
    Real Broker, LLC - Chester

    1 month on neighborhoods.com

  18. $380,000

    • 4 bed
    • 2 bath
    • 1277 SqFt
    213 BYFORD DR
    Doug Ashley Realtors, LLC

    1 month on neighborhoods.com

  19. $265,000

    • 3 bed
    • 1 bath
    • 1967 SqFt
    1904 PONDTOWN RD
    Keller Williams Flagship

    1 month on neighborhoods.com

  20. $350,000

    • 2 bed
    • 3 bath
    • 1518 SqFt
    522 HIGH ST
    Benson & Mangold, LLC

    1 month on neighborhoods.com

  21. $1,650,000

    • 9 bed
    • 7 bath
    • 4776 SqFt
    8796 MARYLAND PKWY
    Coldwell Banker Chesapeake Real Estate Company

    1 month on neighborhoods.com

  22. $275,000

    • 3 bed
    • 1 bath
    • 1248 SqFt
    956 WASHINGTON AVE
    Doug Ashley Realtors, LLC

    2 months on neighborhoods.com

  23. $1,450,000

    • 4 bed
    • 5 bath
    • 4257 SqFt
    22470 FAIRGALE FARM LN
    Fairgale Properties
    Gunther-McClary Real Estate

    2 months on neighborhoods.com

  24. $320,000

    • 3 bed
    • 2 bath
    • 1232 SqFt
    8706 ELM RD
    Tolchester Estates
    Doug Ashley Realtors, LLC

    3 months on neighborhoods.com

  25. $365,000

    • 3 bed
    • 2 bath
    • 1120 SqFt
    240 MERGANSER DR
    Chesapeake Real Estate Associates, LLC

    3 months on neighborhoods.com

  26. $898,000

    • 3 bed
    • 4 bath
    • 2172 SqFt
    226 S WATER ST
    Gunther-McClary Real Estate

    3 months on neighborhoods.com

  27. $550,000

    • 5 bed
    • 4 bath
    • 3816 SqFt
    103 SUTTON WAY
    Coventry Farms
    TTR Sotheby's International Realty

    3 months on neighborhoods.com

  28. $519,900

    • 3 bed
    • 3 bath
    • 2268 SqFt
    101 COLEMAN DR
    Skipper Lands
    Coldwell Banker Chesapeake Real Estate Company

    4 months on neighborhoods.com

  29. $829,000

    • 3 bed
    • 4 bath
    • 2472 SqFt
    106 QUEEN ST
    Chesapeake Real Estate Associates, LLC

    4 months on neighborhoods.com

  30. $1,395,000

    • 4 bed
    • 4 bath
    • 3383 SqFt
    8276 BROAD NECK RD
    Coldwell Banker Chesapeake Real Estate Company

    4 months on neighborhoods.com

Viewing 1-30 of 51

The City of Chestertown: Overview

Chestertown is a city in Maryland.

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