6,890

Chestertown, MD Homes

Section Image
  • 21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    /31

    $191,000

    Sold Oct 03, 2025

    21317 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,269 Sq Ft
    • Built 1955

    Last Sold Summary

    • $151/SF
    • 67 Days On Market

    Current Estimated Value $187,860

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
    • 811 S Meadowview Dr, Chestertown, MD 21620
      811 S Meadowview Dr, Chestertown, MD 21620
      811 S Meadowview Dr, Chestertown, MD 21620
      /45

      Est $472,091

      Not Listed For Sale

      811 S Meadowview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,064 Sq Ft
      • Built 2002
      811 S Meadowview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

  • 132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    132 Prospect St, Chestertown, MD 21620
    /20

    $155,000

    Sold May 13, 2026

    132 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1949

    Last Sold Summary

    • 22% Below List Price
    • $170/SF
    • 74 Days On Market

    Current Estimated Value $168,726

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
    • 100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      /39

      Est $340,850

      Not Listed For Sale

      100 Malone Ave, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,444 Sq Ft
      • Built 1967
      100 Malone Ave, Chestertown, MD 21620

      Last Sold Summary

      • 94 Days On Market

  • 108 Oak Leaf Dr, Chestertown, MD 21620
    108 Oak Leaf Dr, Chestertown, MD 21620
    108 Oak Leaf Dr, Chestertown, MD 21620
    /39

    $296,500

    Sold May 22, 2026

    108 Oak Leaf Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,867 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $159/SF
    • 18 Days On Market

    Current Estimated Value $296,665

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    108 Oak Leaf Dr, Chestertown, MD 21620
    • 100 Acorn Dr, Chestertown, MD 21620
      100 Acorn Dr, Chestertown, MD 21620
      100 Acorn Dr, Chestertown, MD 21620
      /27

      Est $300,299

      Not Listed For Sale

      100 Acorn Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,930 Sq Ft
      • Built 2004
      100 Acorn Dr, Chestertown, MD 21620

      Last Sold Summary

      • 164 Days On Market

  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /67

    $424,000

    Sold Jan 30, 2026

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft
    • Built 2006

    Last Sold Summary

    • $188/SF
    • 159 Days On Market

    Current Estimated Value $442,721

    Last Listing Agent Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
    • 204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      /54

      Est $411,341

      Not Listed For Sale

      204 Richard Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft
      • Built 1972
      204 Richard Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

  • 23264 Clarissa Rd, Chestertown, MD 21620
    23264 Clarissa Rd, Chestertown, MD 21620
    /2

    $365,000

    Sold Jul 13, 2026

    23264 Clarissa Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 2021

    Last Sold Summary

    • $292/SF
    • 4 Days On Market

    Current Estimated Value $363,234

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    23264 Clarissa Rd, Chestertown, MD 21620
    • 898 Washington Ave, Chestertown, MD 21620
      898 Washington Ave, Chestertown, MD 21620
      898 Washington Ave, Chestertown, MD 21620
      /34

      Est $254,496

      Not Listed For Sale

      898 Washington Ave, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,384 Sq Ft
      • Built 1967
      898 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

  • 10050 Forrest Ln, Chestertown, MD 21620
    10050 Forrest Ln, Chestertown, MD 21620
    10050 Forrest Ln, Chestertown, MD 21620
    /49

    $905,000

    Sold Nov 14, 2025

    10050 Forrest Ln, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1993

    Last Sold Summary

    • $497/SF
    • 4 Days On Market

    Current Estimated Value $895,107

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
    • 307 Washington Ave, Chestertown, MD 21620
      307 Washington Ave, Chestertown, MD 21620
      307 Washington Ave, Chestertown, MD 21620
      /56

      Est $787,943

      Not Listed For Sale

      307 Washington Ave, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,355 Sq Ft
      • Built 1936
      307 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 130 Days On Market

  • 201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    201 Birch Run Rd, Chestertown, MD 21620
    /24

    $430,000

    Sold May 29, 2026

    201 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $271/SF
    • 23 Days On Market

    Current Estimated Value $435,004

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
    • 24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      /24

      Est $355,259

      Not Listed For Sale

      24291 Chestertown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1962
      24291 Chestertown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 64 Days On Market

  • 10761 Kasota Rd, Chestertown, MD 21620
    10761 Kasota Rd, Chestertown, MD 21620
    10761 Kasota Rd, Chestertown, MD 21620
    /47

    $872,500

    Sold Nov 21, 2025

    10761 Kasota Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,582 Sq Ft
    • Built 2005

    Last Sold Summary

    • $338/SF
    • 32 Days On Market

    Current Estimated Value $799,913

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
    • 425 High St, Chestertown, MD 21620
      425 High St, Chestertown, MD 21620
      425 High St, Chestertown, MD 21620
      /18

      Est $692,678

      Not Listed For Sale

      425 High St, Chestertown, MD 21620

      • Studio
      • 3,114 Sq Ft
      • Built 1920
      425 High St, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • 1014 Twin Ct, Chestertown, MD 21620
    1014 Twin Ct, Chestertown, MD 21620
    1014 Twin Ct, Chestertown, MD 21620
    /29

    $525,000

    Sold Jun 26, 2026

    1014 Twin Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,817 Sq Ft
    • Built 2017

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 0 Days On Market

    Current Estimated Value $494,966

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    1014 Twin Ct, Chestertown, MD 21620
    • 100 Foxview Ct, Chestertown, MD 21620
      100 Foxview Ct, Chestertown, MD 21620
      100 Foxview Ct, Chestertown, MD 21620
      /41

      Est $464,951

      Not Listed For Sale

      100 Foxview Ct, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,000 Sq Ft
      • Built 1999
      100 Foxview Ct, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

  • 127 Char Nor Manor Blvd, Chestertown, MD 21620
    127 Char Nor Manor Blvd, Chestertown, MD 21620
    127 Char Nor Manor Blvd, Chestertown, MD 21620
    /42

    $355,000

    Sold Oct 02, 2025

    127 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • Built 1963

    Last Sold Summary

    • $427/SF
    • 10 Days On Market

    Current Estimated Value $355,311

    Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

    127 Char Nor Manor Blvd, Chestertown, MD 21620
    • 306 Mayfair Dr, Chestertown, MD 21620
      306 Mayfair Dr, Chestertown, MD 21620
      306 Mayfair Dr, Chestertown, MD 21620
      /56

      Est $484,690

      Not Listed For Sale

      306 Mayfair Dr, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 1995
      306 Mayfair Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    /90

    $585,000

    Sold Nov 13, 2025

    103 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft
    • Built 2008

    Last Sold Summary

    • $105/SF
    • 54 Days On Market

    Current Estimated Value $576,244

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
    • 116 Oak Leaf Dr, Chestertown, MD 21620
      116 Oak Leaf Dr, Chestertown, MD 21620
      116 Oak Leaf Dr, Chestertown, MD 21620
      /38

      Est $300,214

      Not Listed For Sale

      116 Oak Leaf Dr, Chestertown, MD 21620

      • 2 Beds
      • 4 Baths
      • 1,867 Sq Ft
      • Built 2004
      116 Oak Leaf Dr, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

  • 10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    /50

    $350,000

    Sold Mar 27, 2026

    10751 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft
    • Built 1975

    Last Sold Summary

    • $180/SF
    • 175 Days On Market

    Current Estimated Value $360,119

    Last Listing Agent Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, Chestertown, MD 21620
    • 104 Oak Leaf Dr, Chestertown, MD 21620
      104 Oak Leaf Dr, Chestertown, MD 21620
      104 Oak Leaf Dr, Chestertown, MD 21620
      /17

      Est $302,377

      Not Listed For Sale

      104 Oak Leaf Dr, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 1,840 Sq Ft
      • Built 2003
      104 Oak Leaf Dr, Chestertown, MD 21620

      Last Sold Summary

      • 38 Days On Market

  • 107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    /23

    $290,000

    Sold Aug 13, 2025

    107 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 2005

    Last Sold Summary

    • $210/SF
    • 234 Days On Market

    Current Estimated Value $306,357

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
    • 307 Cedar St, Chestertown, MD 21620
      307 Cedar St, Chestertown, MD 21620
      307 Cedar St, Chestertown, MD 21620
      /24

      Est $301,269

      Not Listed For Sale

      307 Cedar St, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft
      • Built 1962
      307 Cedar St, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 10087 John Carvill Rd, Chestertown, MD 21620
    10087 John Carvill Rd, Chestertown, MD 21620
    10087 John Carvill Rd, Chestertown, MD 21620
    /63

    $695,000

    Sold May 18, 2026

    10087 John Carvill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1983

    Last Sold Summary

    • $444/SF
    • 8 Days On Market

    Current Estimated Value $711,243

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10087 John Carvill Rd, Chestertown, MD 21620
    • 109 Birch Run Rd, Chestertown, MD 21620
      109 Birch Run Rd, Chestertown, MD 21620
      109 Birch Run Rd, Chestertown, MD 21620
      /54

      Est $454,214

      Not Listed For Sale

      109 Birch Run Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,428 Sq Ft
      • Built 1978
      109 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /35

    $650,000

    Sold Mar 10, 2026

    200 Washington Ave, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft
    • Built 1900

    Last Sold Summary

    • $223/SF
    • 105 Days On Market

    Current Estimated Value $673,196

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
    • 23530 Clarissa Rd, Chestertown, MD 21620
      23530 Clarissa Rd, Chestertown, MD 21620
      23530 Clarissa Rd, Chestertown, MD 21620
      /32

      Est $355,091

      Not Listed For Sale

      23530 Clarissa Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft
      • Built 1993
      23530 Clarissa Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 100 Little Harbor Way, Chestertown, MD 21620
    100 Little Harbor Way, Chestertown, MD 21620
    /2

    $680,000

    Sold Aug 08, 2025

    100 Little Harbor Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 2015

    Last Sold Summary

    • $309/SF
    • 82 Days On Market

    Current Estimated Value $703,754

    Last Listing Agent Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
    • 27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      /45

      Est $535,605

      Not Listed For Sale

      27325 Preston Ln, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,824 Sq Ft
      • Built 2000
      27325 Preston Ln, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /54

    $250,000

    Sold Apr 10, 2026

    112 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2023

    Last Sold Summary

    • $195/SF
    • 36 Days On Market

    Current Estimated Value $253,437

    Last Listing Agent April Heim Rosendale Realty

    112 Metcalf Rd, Chestertown, MD 21620
    • 8489 Broad Neck Rd, Chestertown, MD 21620
      8489 Broad Neck Rd, Chestertown, MD 21620
      8489 Broad Neck Rd, Chestertown, MD 21620
      /25

      Est $323,723

      Not Listed For Sale

      8489 Broad Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft
      • Built 1960
      8489 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • 221 Richard Dr, Chestertown, MD 21620
    221 Richard Dr, Chestertown, MD 21620
    221 Richard Dr, Chestertown, MD 21620
    /41

    $398,000

    Sold Oct 24, 2025

    221 Richard Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,711 Sq Ft
    • Built 1972

    Last Sold Summary

    • $233/SF
    • 3 Days On Market

    Current Estimated Value $403,551

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
    • 10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      /17

      Est $281,339

      Not Listed For Sale

      10355 Bunting Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 2002
      10355 Bunting Rd, Chestertown, MD 21620

      Last Sold Summary

      • 23 Days On Market

  • 303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    /32

    $364,000

    Sold Jan 16, 2026

    303 E Campus Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft
    • Built 1963

    Last Sold Summary

    • $238/SF
    • 11 Days On Market

    Current Estimated Value $361,577

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
    • 23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      /21

      Est $315,679

      Not Listed For Sale

      23240 Clarissa Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23240 Clarissa Rd, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

  • 215 Fairview Dr, Chestertown, MD 21620
    215 Fairview Dr, Chestertown, MD 21620
    215 Fairview Dr, Chestertown, MD 21620
    /57

    $435,000

    Sold Jul 16, 2026

    215 Fairview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,784 Sq Ft
    • Built 2004

    Last Sold Summary

    • 2% Above List Price
    • $244/SF
    • 3 Days On Market

    Current Estimated Value $426,701

    Last Listing Agent Mary Julie Long & Foster Real Estate, Inc.

    215 Fairview Dr, Chestertown, MD 21620
    • 306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      /20

      Est $269,742

      Not Listed For Sale

      306 Roosevelt Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,152 Sq Ft
      • Built 1966
      306 Roosevelt Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

Showing Results 481 - 520, Page 13 of 18

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