6,952

Homes in ZIP Code 21620

Section Image
    • 7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      /15

      Est $232,279

      Not Listed For Sale

      7509 Sunburst Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1989
      7509 Sunburst Ave, Chestertown, MD 21620

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Tiffany Dodson Samson Properties

  • 110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    /30

    $541,500

    Sold Jul 10, 2026

    110 S Queen St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,785 Sq Ft
    • Built 1914

    Last Sold Summary

    • 3% Above List Price
    • $303/SF
    • 17 Days On Market

    Current Estimated Value $512,724

    Last Listing Agent J.P. Graham Cross Street Realtors LLC

    110 S Queen St, 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 $479,720

      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

      Last Listing Agent Christine Leonard Redfin Corp

  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $244,000

    Sold Jul 27, 2026

    21217 Texas Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1952

    Last Sold Summary

    • 8% Below List Price
    • $268/SF
    • 83 Days On Market

    Current Estimated Value $242,218

    Last Listing Agent Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
    • 100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      /39

      Est $346,034

      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

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 1517 Dudley Corners Rd, Millington, MD 21651
    1517 Dudley Corners Rd, Millington, MD 21651
    1517 Dudley Corners Rd, Millington, MD 21651
    /40

    $220,000

    Sold May 18, 2026

    1517 Dudley Corners Rd, Millington, MD 21651

    • 6 Beds
    • 3 Baths
    • 2,948 Sq Ft
    • Built 1961

    Last Sold Summary

    • 34% Below List Price
    • $75/SF
    • 24 Days On Market

    Current Estimated Value $277,587

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    1517 Dudley Corners Rd, Millington, MD 21651
    • 100 Acorn Dr, Chestertown, MD 21620
      100 Acorn Dr, Chestertown, MD 21620
      100 Acorn Dr, Chestertown, MD 21620
      /27

      Est $296,322

      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

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 113 Pear Tree Point Rd, Chestertown, MD 21620
    113 Pear Tree Point Rd, Chestertown, MD 21620
    /2

    $175,000

    Sold Jun 05, 2026

    113 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • Built 1973

    Last Sold Summary

    • 30% Below List Price
    • $135/SF
    • 47 Days On Market

    Current Estimated Value $208,310

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    113 Pear Tree Point Rd, Chestertown, MD 21620
    • 204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      /54

      Est $403,966

      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

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 217 Philosophers Terrace, Chestertown, MD 21620
    217 Philosophers Terrace, Chestertown, MD 21620
    /2

    $370,000

    Sold May 01, 2026

    217 Philosophers Terrace, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • Built 1950

    Last Sold Summary

    • 14% Above List Price
    • $264/SF
    • 3 Days On Market

    Current Estimated Value $361,801

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    217 Philosophers Terrace, Chestertown, MD 21620
    • 898 Washington Ave, Chestertown, MD 21620
      898 Washington Ave, Chestertown, MD 21620
      898 Washington Ave, Chestertown, MD 21620
      /34

      Est $261,902

      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

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    /51

    $361,500

    Sold Dec 19, 2025

    517 High St, Chestertown, MD 21620

    • Studio
    • 1,728 Sq Ft
    • Built 1900

    Last Sold Summary

    • $209/SF
    • 51 Days On Market

    Current Estimated Value $374,510

    Last Listing Agent Kristie Midash L. C. Parker Real Estate

    517 High St, Chestertown, MD 21620
    • 307 Washington Ave, Chestertown, MD 21620
      307 Washington Ave, Chestertown, MD 21620
      307 Washington Ave, Chestertown, MD 21620
      /56

      Est $787,494

      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

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • 515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    /36

    $495,000

    Sold Apr 17, 2026

    515 N Kent St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • Built 1965

    Last Sold Summary

    • $223/SF
    • 1 Day On Market

    Current Estimated Value $493,279

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
    • 24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      24291 Chestertown Rd, Chestertown, MD 21620
      /24

      Est $370,074

      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

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • 0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    /2

    $75,000

    Sold Sep 26, 2025

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620

    • Land
    • 1.49 Acres
    • $50,336 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    • 425 High St, Chestertown, MD 21620
      425 High St, Chestertown, MD 21620
      425 High St, Chestertown, MD 21620
      /18

      Est $671,927

      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

      Last Listing Agent William Norris Select Land & Homes, LLC

  • 225 Duke of Kent St, Chestertown, MD 21620
    225 Duke of Kent St, Chestertown, MD 21620
    225 Duke of Kent St, Chestertown, MD 21620
    /34

    $395,000

    Sold Nov 10, 2025

    225 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2000

    Last Sold Summary

    • $214/SF
    • 16 Days On Market

    Current Estimated Value $400,574

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
    • 24095 Chestertown Rd, Chestertown, MD 21620
      24095 Chestertown Rd, Chestertown, MD 21620
      24095 Chestertown Rd, Chestertown, MD 21620
      /45

      Est $297,227

      Not Listed For Sale

      24095 Chestertown Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,104 Sq Ft
      • Built 1972
      24095 Chestertown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 87 Days On Market

      Last Listing Agent Lona Todd Taylor Properties

  • 207 Lincoln Dr, Chestertown, MD 21620
    207 Lincoln Dr, Chestertown, MD 21620
    207 Lincoln Dr, Chestertown, MD 21620
    /24

    $141,000

    Sold Sep 03, 2026

    207 Lincoln Dr, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,152 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Above List Price
    • $122/SF
    • 4 Days On Market

    Current Estimated Value $240,008

    Last Listing Agent Jennifer Cernik Monument Sotheby's International Realty

    207 Lincoln Dr, Chestertown, MD 21620
    • 100 Foxview Ct, Chestertown, MD 21620
      100 Foxview Ct, Chestertown, MD 21620
      100 Foxview Ct, Chestertown, MD 21620
      /41

      Est $469,052

      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

      Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

  • 23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    /45

    $1,150,000

    Sold Dec 10, 2025

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft
    • Built 1990

    Last Sold Summary

    • $259/SF
    • 361 Days On Market

    Current Estimated Value $1,144,916

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
    • 306 Mayfair Dr, Chestertown, MD 21620
      306 Mayfair Dr, Chestertown, MD 21620
      306 Mayfair Dr, Chestertown, MD 21620
      /56

      Est $478,536

      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

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 221 Dutchess Rd, Chestertown, MD 21620
    221 Dutchess Rd, Chestertown, MD 21620
    /2

    $228,000

    Sold Jul 13, 2026

    221 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,260 Sq Ft
    • Built 1974

    Last Sold Summary

    • $101/SF
    • 0 Days On Market

    Current Estimated Value $231,877

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    221 Dutchess Rd, 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 $298,617

      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

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • 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 $190,061

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
    • 10575 Hyala Ct, Chestertown, MD 21620
      10575 Hyala Ct, Chestertown, MD 21620
      10575 Hyala Ct, Chestertown, MD 21620
      /22

      Est $357,843

      Not Listed For Sale

      10575 Hyala Ct, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,978 Sq Ft
      • Built 2003
      10575 Hyala Ct, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Laura Anthony Benson & Mangold, LLC

  • 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 $156,409

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    132 Prospect St, 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 $300,183

      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

      Last Listing Agent Krystal Zellner Crown Homes Real Estate

  • 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 $299,380

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    108 Oak Leaf Dr, Chestertown, MD 21620
    • 307 Cedar St, Chestertown, MD 21620
      307 Cedar St, Chestertown, MD 21620
      307 Cedar St, Chestertown, MD 21620
      /24

      Est $297,682

      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

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • 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 $443,019

    Last Listing Agent Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
    • 10624 Millbrook Dr, Chestertown, MD 21620
      10624 Millbrook Dr, Chestertown, MD 21620
      10624 Millbrook Dr, Chestertown, MD 21620
      /20

      Est $239,518

      Not Listed For Sale

      10624 Millbrook Dr, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,000 Sq Ft
      • Built 1988
      10624 Millbrook Dr, Chestertown, MD 21620

      Last Sold Summary

      • 17 Days On Market

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

  • 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
    • 109 Birch Run Rd, Chestertown, MD 21620
      109 Birch Run Rd, Chestertown, MD 21620
      109 Birch Run Rd, Chestertown, MD 21620
      /54

      Est $447,955

      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

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    22481 Goose Hollow Dr, Chestertown, MD 21620
    /88

    $335,320

    Sold Aug 18, 2026

    22481 Goose Hollow Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1984

    Last Sold Summary

    • 20% Above List Price
    • $259/SF
    • 22 Days On Market

    Current Estimated Value $309,473

    Last Listing Agent Tom Atwood Keller Williams Legacy

    22481 Goose Hollow Dr, Chestertown, MD 21620
    • 23530 Clarissa Rd, Chestertown, MD 21620
      23530 Clarissa Rd, Chestertown, MD 21620
      23530 Clarissa Rd, Chestertown, MD 21620
      /32

      Est $363,929

      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

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • 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 $902,217

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
    • 24581 Willow Oak Ln, Chestertown, MD 21620
      24581 Willow Oak Ln, Chestertown, MD 21620
      24581 Willow Oak Ln, Chestertown, MD 21620
      /5

      Not Listed For Sale

      24581 Willow Oak Ln, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 2007
      24581 Willow Oak Ln, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • 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 $438,767

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620

Showing Results 481 - 520, Page 13 of 18

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