6,890

Chestertown, MD Homes

Section Image
  • 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 $247,476

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $290,802

      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

  • 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 $810,718

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, 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 $584,937

      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

  • 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
    • 9769 Augustine Herman Hwy, Chestertown, MD 21620
      9769 Augustine Herman Hwy, Chestertown, MD 21620
      9769 Augustine Herman Hwy, Chestertown, MD 21620
      /46

      Est $313,339

      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

  • 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 $445,081

    Last Listing Agent Crystal Smith RE/MAX Executive

    118 Grant Ct, Chestertown, MD 21620
    • 202 Glen St, Chestertown, MD 21620
      202 Glen St, Chestertown, MD 21620
      202 Glen St, Chestertown, MD 21620
      /37

      Est $293,287

      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

  • 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 $464,845

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    104 Garland Ave, Chestertown, MD 21620
    • 201 Pondview Ct, Chestertown, MD 21620
      201 Pondview Ct, Chestertown, MD 21620
      201 Pondview Ct, Chestertown, MD 21620
      /37

      Est $556,257

      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

  • 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
    • 106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      /43

      Est $412,437

      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

  • 7761 Broad Neck Rd, Chestertown, MD 21620
    7761 Broad Neck Rd, Chestertown, MD 21620
    /2

    $1,550,000

    Sold Jun 29, 2026

    7761 Broad Neck Rd, Chestertown, MD 21620

    • 5 Beds
    • 2.5 Baths
    • 2,700 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Above List Price
    • $574/SF
    • 0 Days On Market

    Current Estimated Value $1,067,850

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7761 Broad Neck Rd, Chestertown, MD 21620
    • 26865 Mallard Rd, Chestertown, MD 21620
      26865 Mallard Rd, Chestertown, MD 21620
      26865 Mallard Rd, Chestertown, MD 21620
      /49

      Est $959,542

      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

  • 7425 Wilkins Ln, Chestertown, MD 21620
    7425 Wilkins Ln, Chestertown, MD 21620
    7425 Wilkins Ln, Chestertown, MD 21620
    /29

    $315,000

    Sold Aug 29, 2025

    7425 Wilkins Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,341 Sq Ft
    • Built 1962

    Last Sold Summary

    • $235/SF
    • 6 Days On Market

    Current Estimated Value $301,708

    Last Listing Agent LAURIE KREIDER Realty ONE Group Unlimited

    7425 Wilkins Ln, Chestertown, MD 21620
    • 109 N Water St, Chestertown, MD 21620
      109 N Water St, Chestertown, MD 21620
      109 N Water St, Chestertown, MD 21620
      /51

      Est $996,172

      Not Listed For Sale

      109 N Water St, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 3,030 Sq Ft
      • Built 1739
      109 N Water St, Chestertown, MD 21620

      Last Sold Summary

      • 106 Days On Market

  • 136 Truslow Farm Ln, Chestertown, MD 21620
    136 Truslow Farm Ln, Chestertown, MD 21620
    136 Truslow Farm Ln, Chestertown, MD 21620
    /12

    $560,000

    Sold Oct 31, 2025

    136 Truslow Farm Ln, Chestertown, MD 21620

    • Land
    • 3.01 Acres
    • $186,047 per Acre

    Last Sold Summary

    • 111 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    136 Truslow Farm Ln, Chestertown, MD 21620
    • 10061 Flatland Rd, Chestertown, MD 21620
      10061 Flatland Rd, Chestertown, MD 21620
      10061 Flatland Rd, Chestertown, MD 21620
      /21

      Est $332,597

      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

  • 121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    121 Primrose Rd, Chestertown, MD 21620
    /22

    $325,000

    Sold Mar 18, 2026

    121 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,034 Sq Ft
    • Built 1971

    Last Sold Summary

    • 19% Below List Price
    • $160/SF
    • 90 Days On Market

    Current Estimated Value $342,731

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    121 Primrose Rd, 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

  • 25195 Lovers Ln, Chestertown, MD 21620
    25195 Lovers Ln, Chestertown, MD 21620
    /2

    $350,000

    Sold Dec 15, 2025

    25195 Lovers Ln, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 1,002 Sq Ft
    • Built 1980

    Last Sold Summary

    • $349/SF

    Current Estimated Value $347,208

    Last Listing Agent William Norris Select Land & Homes, LLC

    25195 Lovers Ln, Chestertown, MD 21620
    • 1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      /30

      Est $400,670

      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

    • 8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      /52

      Est $655,586

      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

    • 110 Birch Run Rd, Chestertown, MD 21620
      110 Birch Run Rd, Chestertown, MD 21620
      110 Birch Run Rd, Chestertown, MD 21620
      /29

      Est $654,298

      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

    • 209 N Queen St, Chestertown, MD 21620
      209 N Queen St, Chestertown, MD 21620
      209 N Queen St, Chestertown, MD 21620
      /63

      Est $598,682

      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

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

      Est $469,092

      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

    • 23795 Lands End Rd, Chestertown, MD 21620
      23795 Lands End Rd, Chestertown, MD 21620
      23795 Lands End Rd, Chestertown, MD 21620
      /24

      Est $331,629

      Not Listed For Sale

      23795 Lands End Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,088 Sq Ft
      • Built 1927
      23795 Lands End Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

    • 123 High St, Chestertown, MD 21620
      123 High St, Chestertown, MD 21620
      123 High St, Chestertown, MD 21620
      /29

      Est $857,272

      Not Listed For Sale

      123 High St, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,855 Sq Ft
      • Built 1870
      123 High St, Chestertown, MD 21620

      Last Sold Summary

      • 25 Days On Market

    • 9062 Fairlee Rd, Chestertown, MD 21620
      9062 Fairlee Rd, Chestertown, MD 21620
      9062 Fairlee Rd, Chestertown, MD 21620
      /37

      Est $369,081

      Not Listed For Sale

      9062 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 1990
      9062 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 47 Days On Market

    • 7938 Radcliffe Rd, Chestertown, MD 21620
      7938 Radcliffe Rd, Chestertown, MD 21620
      7938 Radcliffe Rd, Chestertown, MD 21620
      /44

      Est $581,947

      Not Listed For Sale

      7938 Radcliffe Rd, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 2,408 Sq Ft
      • Built 1976
      7938 Radcliffe Rd, Chestertown, MD 21620

      Last Sold Summary

      • 115 Days On Market

    • 5594 Langford Bay Rd, Chestertown, MD 21620
      5594 Langford Bay Rd, Chestertown, MD 21620
      5594 Langford Bay Rd, Chestertown, MD 21620
      /40

      Est $768,521

      Not Listed For Sale

      5594 Langford Bay Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,682 Sq Ft
      • Built 1956
      5594 Langford Bay Rd, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

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

      Est $389,330

      Not Listed For Sale

      214 Richard Dr, Chestertown, MD 21620

      • 2 Beds
      • 2.5 Baths
      • 1,723 Sq Ft
      • Built 1974
      214 Richard Dr, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

    • 313 S Queen St, Chestertown, MD 21620
      313 S Queen St, Chestertown, MD 21620
      313 S Queen St, Chestertown, MD 21620
      /57

      Est $448,707

      Not Listed For Sale

      313 S Queen St, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 1,995 Sq Ft
      • Built 1997
      313 S Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 1 Day On Market

    • 7121 Quaker Neck Rd, Chestertown, MD 21620
      7121 Quaker Neck Rd, Chestertown, MD 21620
      7121 Quaker Neck Rd, Chestertown, MD 21620
      /22

      Est $127,038

      Not Listed For Sale

      7121 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 930 Sq Ft
      • Built 1959
      7121 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13 Days On Market

    • 529 Cannon St, Chestertown, MD 21620
      529 Cannon St, Chestertown, MD 21620
      529 Cannon St, Chestertown, MD 21620
      /30

      Est $405,355

      Not Listed For Sale

      529 Cannon St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 1900
      529 Cannon St, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

    • 813 S Meadowview Dr, Chestertown, MD 21620
      813 S Meadowview Dr, Chestertown, MD 21620
      813 S Meadowview Dr, Chestertown, MD 21620
      /35

      Est $411,056

      Not Listed For Sale

      813 S Meadowview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,509 Sq Ft
      • Built 2002
      813 S Meadowview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

    • 703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      703 High St, Chestertown, MD 21620
      /31

      Est $249,269

      Not Listed For Sale

      703 High St, Chestertown, MD 21620

      • 4 Beds
      • 1.5 Baths
      • 1,200 Sq Ft
      • Built 1951
      703 High St, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

    • 1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      1006 Twin Ct, Chestertown, MD 21620
      /50

      Est $377,272

      Not Listed For Sale

      1006 Twin Ct, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,800 Sq Ft
      • Built 1989
      1006 Twin Ct, Chestertown, MD 21620

      Last Sold Summary

      • 96 Days On Market

    • 23120 Club Terrace, Chestertown, MD 21620
      23120 Club Terrace, Chestertown, MD 21620
      23120 Club Terrace, Chestertown, MD 21620
      /41

      Est $388,370

      Not Listed For Sale

      23120 Club Terrace, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,789 Sq Ft
      • Built 1969
      23120 Club Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 12 Days On Market

    • 25285 Foxchase Dr, Chestertown, MD 21620
      25285 Foxchase Dr, Chestertown, MD 21620
      25285 Foxchase Dr, Chestertown, MD 21620
      /39

      Est $565,607

      Not Listed For Sale

      25285 Foxchase Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,010 Sq Ft
      • Built 1992
      25285 Foxchase Dr, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

Showing Results 521 - 560, Page 14 of 18

Maryland Kent County

Real Estate & Homes

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

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 © 2026 CoStar Group