6,952

Homes in ZIP Code 21620

Section Image
    • 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

  • 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 $799,853

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
    • 27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      27325 Preston Ln, Chestertown, MD 21620
      /45

      Est $526,820

      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

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • 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 $503,112

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    1014 Twin Ct, 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 $316,894

      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

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 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 $360,114

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

    127 Char Nor Manor Blvd, Chestertown, MD 21620
    • 23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      /21

      Est $318,703

      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

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

  • 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 $591,092

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
    • 306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      /20

      Est $271,574

      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

      Last Listing Agent Theresa Stewart Patterson-Schwartz Real Estate

  • 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 $352,798

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

    10751 Millbrook Dr, Chestertown, MD 21620
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $297,976

      Not Listed For Sale

      27370 Morgnec Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1969
      27370 Morgnec Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • 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 $717,269

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10087 John Carvill Rd, Chestertown, MD 21620
    • 223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      223 S Queen St, Chestertown, MD 21620
      /47

      Est $592,871

      Not Listed For Sale

      223 S Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 2006
      223 S Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 166 Days On Market

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • 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 $670,710

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
    • 9769 Augustine Herman Hwy, Chestertown, MD 21620
      9769 Augustine Herman Hwy, Chestertown, MD 21620
      9769 Augustine Herman Hwy, Chestertown, MD 21620
      /46

      Est $315,117

      Not Listed For Sale

      9769 Augustine Herman Hwy, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,456 Sq Ft
      • Built 1961
      9769 Augustine Herman Hwy, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Rosella Hunter Remax Vision

  • 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 $250,714

    Last Listing Agent April Heim Rosendale Realty

    112 Metcalf Rd, Chestertown, MD 21620
    • 202 Glen St, Chestertown, MD 21620
      202 Glen St, Chestertown, MD 21620
      202 Glen St, Chestertown, MD 21620
      /37

      Est $290,449

      Not Listed For Sale

      202 Glen St, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,252 Sq Ft
      • Built 1966
      202 Glen St, Chestertown, MD 21620

      Last Sold Summary

      • 104 Days On Market

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

  • 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
    • 201 Pondview Ct, Chestertown, MD 21620
      201 Pondview Ct, Chestertown, MD 21620
      201 Pondview Ct, Chestertown, MD 21620
      /37

      Est $563,564

      Not Listed For Sale

      201 Pondview Ct, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 3,016 Sq Ft
      • Built 2001
      201 Pondview Ct, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • 7903 Radcliffe Rd, Chestertown, MD 21620
    7903 Radcliffe Rd, Chestertown, MD 21620
    7903 Radcliffe Rd, Chestertown, MD 21620
    /79

    $705,000

    Sold Aug 19, 2026

    7903 Radcliffe Rd, Chestertown, MD 21620

    • 3 Beds
    • 4 Baths
    • 4,037 Sq Ft
    • Built 1988

    Last Sold Summary

    • 13% Above List Price
    • $175/SF
    • 3 Days On Market

    Current Estimated Value $723,239

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    7903 Radcliffe Rd, Chestertown, MD 21620
    • 106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      /43

      Est $420,386

      Not Listed For Sale

      106 Devon Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 2001
      106 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 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 $365,872

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
    • 26865 Mallard Rd, Chestertown, MD 21620
      26865 Mallard Rd, Chestertown, MD 21620
      26865 Mallard Rd, Chestertown, MD 21620
      /49

      Est $996,925

      Not Listed For Sale

      26865 Mallard Rd, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 3,355 Sq Ft
      • Built 1963
      26865 Mallard Rd, Chestertown, MD 21620

      Last Sold Summary

      • 182 Days On Market

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • 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 $427,300

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

    215 Fairview Dr, Chestertown, MD 21620
    • 10061 Flatland Rd, Chestertown, MD 21620
      10061 Flatland Rd, Chestertown, MD 21620
      10061 Flatland Rd, Chestertown, MD 21620
      /21

      Est $322,961

      Not Listed For Sale

      10061 Flatland Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 2,376 Sq Ft
      • Built 1969
      10061 Flatland Rd, Chestertown, MD 21620

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $185,000

    Sold Aug 10, 2026

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    • Land
    • 1.95 Acres
    • $94,872 per Acre

    Last Sold Summary

    • 13% Below List Price
    • 675 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    Lot 9 Prestwick Dr, Chestertown, MD 21620
    • 10262 John Carvill Rd, Chestertown, MD 21620
      10262 John Carvill Rd, Chestertown, MD 21620
      10262 John Carvill Rd, Chestertown, MD 21620
      /59

      Est $1,522,008

      Not Listed For Sale

      10262 John Carvill Rd, Chestertown, MD 21620

      • 5 Beds
      • 2 Baths
      • 3,788 Sq Ft
      • Built 1953
      10262 John Carvill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • 7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    /24

    $235,000

    Sold Jan 20, 2026

    7521 Pine Ave, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1969

    Last Sold Summary

    • $226/SF
    • 12 Days On Market

    Current Estimated Value $246,818

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620
    • 1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      /30

      Est $412,941

      Not Listed For Sale

      1 Reed Ct, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 1,854 Sq Ft
      • Built 1988
      1 Reed Ct, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Carol Tinnin RE/MAX Leading Edge

  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /9

    $800,000

    Sold Jan 15, 2026

    206 Cannon St, Chestertown, MD 21620

    • Land
    • 1.56 Acres
    • $512,821 per Acre

    Last Sold Summary

    • 635 Days On Market

    Current Estimated Value $832,169

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, Chestertown, MD 21620
    • 8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      /52

      Est $648,422

      Not Listed For Sale

      8623 Orchard Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,708 Sq Ft
      • Built 1994
      8623 Orchard Dr, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • 206 Burchard Sawmill Rd, Chestertown, MD 21620
    206 Burchard Sawmill Rd, Chestertown, MD 21620
    /2

    $9,000

    Sold Jul 08, 2026

    206 Burchard Sawmill Rd, Chestertown, MD 21620

    • Land
    • 1.05 Acres
    • $8,571 per Acre

    Last Sold Summary

    • 69% Below List Price
    • 96 Days On Market

    Last Listing Agent Norman Domingo XRealty.NET LLC

    206 Burchard Sawmill Rd, Chestertown, MD 21620
    • 110 Birch Run Rd, Chestertown, MD 21620
      110 Birch Run Rd, Chestertown, MD 21620
      110 Birch Run Rd, Chestertown, MD 21620
      /29

      Est $654,039

      Not Listed For Sale

      110 Birch Run Rd, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,672 Sq Ft
      • Built 2007
      110 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 155 Days On Market

      Last Listing Agent Paula Ruckelshaus Long & Foster Real Estate, Inc.

  • 118 Grant Ct, Chestertown, MD 21620
    118 Grant Ct, Chestertown, MD 21620
    118 Grant Ct, Chestertown, MD 21620
    /37

    $460,000

    Sold Jun 29, 2026

    118 Grant Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft
    • Built 2020

    Last Sold Summary

    • 1% Above List Price
    • $276/SF
    • 2 Days On Market

    Current Estimated Value $456,207

    Last Listing Agent Crystal Smith RE/MAX Executive

    118 Grant Ct, Chestertown, MD 21620
    • 209 N Queen St, Chestertown, MD 21620
      209 N Queen St, Chestertown, MD 21620
      209 N Queen St, Chestertown, MD 21620
      /63

      Est $613,506

      Not Listed For Sale

      209 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,328 Sq Ft
      • Built 1885
      209 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

      Last Listing Agent Andrea Alderdice Long & Foster Real Estate, Inc.

  • 21146 Montana Ave, Chestertown, MD 21620
    21146 Montana Ave, Chestertown, MD 21620
    21146 Montana Ave, Chestertown, MD 21620
    /56

    $290,000

    Sold Sep 11, 2026

    21146 Montana Ave, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Built 1990

    Last Sold Summary

    • $193/SF
    • 12 Days On Market

    Current Estimated Value $309,529

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    21146 Montana Ave, Chestertown, MD 21620
    • 25740 Collins Ave, Chestertown, MD 21620
      25740 Collins Ave, Chestertown, MD 21620
      25740 Collins Ave, Chestertown, MD 21620
      /53

      Est $456,531

      Not Listed For Sale

      25740 Collins Ave, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,389 Sq Ft
      • Built 1956
      25740 Collins Ave, Chestertown, MD 21620

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 104 Garland Ave, Chestertown, MD 21620
    104 Garland Ave, Chestertown, MD 21620
    104 Garland Ave, Chestertown, MD 21620
    /34

    $480,000

    Sold Apr 17, 2026

    104 Garland Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft
    • Built 2005

    Last Sold Summary

    • 9% Above List Price
    • $277/SF
    • 9 Days On Market

    Current Estimated Value $470,899

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    104 Garland Ave, Chestertown, MD 21620
    • 420 Cannon St, Chestertown, MD 21620
      420 Cannon St, Chestertown, MD 21620
      420 Cannon St, Chestertown, MD 21620
      /39

      Est $341,116

      Not Listed For Sale

      420 Cannon St, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,080 Sq Ft
      • Built 1900
      420 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 29 Days On Market

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • 109 S Water St, Chestertown, MD 21620
    109 S Water St, Chestertown, MD 21620
    109 S Water St, Chestertown, MD 21620
    /69

    $650,000

    Sold Feb 27, 2026

    109 S Water St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1900

    Last Sold Summary

    • $315/SF
    • 1 Day On Market

    Current Estimated Value $661,586

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    109 S Water St, Chestertown, MD 21620

Showing Results 521 - 560, Page 14 of 18

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