6,896

Chestertown, MD Homes

Section Image
  • /45

    $485,000

    Sold Jul 18, 2025

    314 Devon Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,420 Sq Ft
    • Built 2010

    Last Sold Summary

    • $142/SF
    • 79 Days On Market

    Current Estimated Value $529,031

    Last Listing Agent Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
    • /29

      Est $868,600

      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

      • $466/SF
      • 25 Days On Market
      • Last Sold Price $865,000
      • Aug 30, 2024

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • /87

    $1,062,800

    Sold Jun 27, 2025

    22153 1st Point Rd, Chestertown, MD 21620

    • 5 Beds
    • 6 Baths
    • 3,078 Sq Ft
    • Built 1975

    Last Sold Summary

    • $345/SF
    • 37 Days On Market

    Current Estimated Value $1,125,093

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
    • /37

      Est $372,970

      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

      • 11% Above List Price
      • $249/SF
      • 47 Days On Market
      • Last Sold Price $335,000
      • May 28, 2024

      Last Listing Agent Brenda Fornos Taylor Properties

  • /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 $436,924

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    104 Garland Ave, Chestertown, MD 21620
    • /44

      Est $598,537

      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

      • 7% Above List Price
      • $233/SF
      • 115 Days On Market
      • Last Sold Price $560,000
      • Apr 21, 2025

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /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 $658,504

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    109 S Water St, Chestertown, MD 21620
    • /22

      Est $274,360

      Not Listed For Sale

      21239 Kansas Ave, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,064 Sq Ft
      • Built 1900
      21239 Kansas Ave, Chestertown, MD 21620

      Last Sold Summary

      • 16% Above List Price
      • $223/SF
      • 71 Days On Market
      • Last Sold Price $237,000
      • Jul 13, 2023

      Last Listing Agent Robin Fithian Rock Hall Properties

  • /5

    $285,000

    Sold Jul 08, 2025

    10141 Flatland Rd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 2,142 Sq Ft
    • Built 1900

    Last Sold Summary

    • $133/SF
    • 8 Days On Market

    Current Estimated Value $307,916

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10141 Flatland Rd, Chestertown, MD 21620
    • /41

      Est $429,921

      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

      • 9% Above List Price
      • $229/SF
      • 1 Day On Market
      • Last Sold Price $395,000
      • May 23, 2024

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /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 $308,448

    Last Listing Agent LAURIE KREIDER Realty ONE Group Unlimited

    7425 Wilkins Ln, Chestertown, MD 21620
    • /57

      Est $483,337

      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

      • 13% Above List Price
      • $214/SF
      • 1 Day On Market
      • Last Sold Price $427,000
      • Jan 29, 2025

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /39

    $350,000

    Sold Jul 18, 2025

    420 Cannon St, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft
    • Built 1900

    Last Sold Summary

    • $324/SF
    • 29 Days On Market

    Current Estimated Value $348,726

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    420 Cannon St, Chestertown, MD 21620
    • /45

      Est $494,317

      Not Listed For Sale

      412 High St, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,867 Sq Ft
      • Built 1920
      412 High St, Chestertown, MD 21620

      Last Sold Summary

      • 77% Above List Price
      • $150/SF
      • 22 Days On Market
      • Last Sold Price $280,000
      • May 19, 2023

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • /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
    • /22

      Est $153,906

      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

      • 43% Above List Price
      • $116/SF
      • 13 Days On Market
      • Last Sold Price $107,500
      • Jan 10, 2025

      Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

  • /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 $337,095

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    121 Primrose Rd, Chestertown, MD 21620
    • /30

      Est $419,949

      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

      • 9% Above List Price
      • $299/SF
      • 2 Days On Market
      • Last Sold Price $385,000
      • Apr 30, 2024

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /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 $349,434

    Last Listing Agent William Norris Select Land & Homes, LLC

    25195 Lovers Ln, Chestertown, MD 21620
    • /35

      Est $454,140

      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

      • 12% Above List Price
      • $269/SF
      • 3 Days On Market
      • Last Sold Price $406,000
      • Nov 07, 2024

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /37

    $295,000

    Sold May 29, 2025

    23315 Sandpiper Rd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,272 Sq Ft
    • Built 1973

    Last Sold Summary

    • $232/SF
    • 120 Days On Market

    Current Estimated Value $309,215

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    23315 Sandpiper Rd, Chestertown, MD 21620
    • /31

      Est $294,349

      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

      • 5% Above List Price
      • $233/SF
      • 4 Days On Market
      • Last Sold Price $280,000
      • Apr 17, 2024

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

    • /50

      Est $375,509

      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

      • 19% Above List Price
      • $175/SF
      • 96 Days On Market
      • Last Sold Price $315,000
      • Apr 16, 2024

      Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    • /41

      Est $410,892

      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

      • 13% Above List Price
      • $204/SF
      • 12 Days On Market
      • Last Sold Price $365,000
      • Aug 13, 2024

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    • /48

      Est $277,769

      Not Listed For Sale

      9020 Cumberland St, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,150 Sq Ft
      • Built 1949
      9020 Cumberland St, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $226/SF
      • 263 Days On Market
      • Last Sold Price $260,000
      • Oct 18, 2024

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    • /57

      Est $843,142

      Not Listed For Sale

      9762 Vogeler Dr, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,521 Sq Ft
      • Built 1900
      9762 Vogeler Dr, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $487/SF
      • 8 Days On Market
      • Last Sold Price $740,000
      • Jan 30, 2024

      Last Listing Agent Tammy Studebaker EXP Realty, LLC

    • /22

      Est $544,732

      Not Listed For Sale

      8983 Orchard Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,084 Sq Ft
      • Built 1989
      8983 Orchard Dr, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $236/SF
      • 129 Days On Market
      • Last Sold Price $492,000
      • Aug 24, 2023

      Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    • /33

      Est $330,082

      Not Listed For Sale

      10589 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,326 Sq Ft
      • Built 1994
      10589 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $211/SF
      • 9 Days On Market
      • Last Sold Price $279,900
      • Jul 09, 2024

      Last Listing Agent David Moore Real Broker, LLC

    • /20

      Est $290,000

      Not Listed For Sale

      8220 Airy Hill Rd, Chestertown, MD 21620

      • Built 1920
      8220 Airy Hill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 19% Below List Price
      • $304/SF
      • 94 Days On Market
      • Last Sold Price $360,000
      • Jan 12, 2024

      Last Listing Agent Sarah King Cross Street Realtors LLC

    • /23

      Est $247,953

      Not Listed For Sale

      104 Conley Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,280 Sq Ft
      • Built 1979
      104 Conley Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $181/SF
      • 12 Days On Market
      • Last Sold Price $232,000
      • May 31, 2024

      Last Listing Agent Jordan Larigan LPT Realty, LLC

    • /41

      Est $467,148

      Not Listed For Sale

      8880 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 2,124 Sq Ft
      • Built 1920
      8880 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 25% Above List Price
      • $177/SF
      • 1 Day On Market
      • Last Sold Price $375,000
      • Jun 29, 2023

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    • /32

      Est $791,280

      Not Listed For Sale

      308 Landing Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,204 Sq Ft
      • Built 2017
      308 Landing Ln, Chestertown, MD 21620

      Last Sold Summary

      • 1% Above List Price
      • $355/SF
      • 10 Days On Market
      • Last Sold Price $782,500
      • May 09, 2025

      Last Listing Agent John Burke Gunther-McClary Real Estate

    • /85

      Est $1,905,867

      Not Listed For Sale

      6880 Pentridge Ln, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 3,931 Sq Ft
      • Built 1998
      6880 Pentridge Ln, Chestertown, MD 21620

      Last Sold Summary

      • 5% Below List Price
      • $509/SF
      • 3 Days On Market
      • Last Sold Price $2,000,000
      • Jun 28, 2023

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

    • /13

      Est $443,868

      Not Listed For Sale

      7671 Waterview Ln, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 2,153 Sq Ft
      • Built 1952
      7671 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 27% Above List Price
      • $163/SF
      • 12 Days On Market
      • Last Sold Price $350,000
      • Jun 26, 2024

      Last Listing Agent Aaron Butler Real Estate Consultants

    • /24

      Est $327,931

      Not Listed For Sale

      7500 Shortall St, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft
      • Built 2018
      7500 Shortall St, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $233/SF
      • 30 Days On Market
      • Last Sold Price $299,900
      • Jan 31, 2025

      Last Listing Agent Lona Todd Taylor Properties

    • /19

      Est $256,554

      Not Listed For Sale

      7519 Quaker Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,136 Sq Ft
      • Built 1956
      7519 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $213/SF
      • 1 Day On Market
      • Last Sold Price $242,500
      • Dec 29, 2023

      Last Listing Agent Lori Sample RE/MAX

    • /11

      Est $177,509

      Not Listed For Sale

      7413 Poplar Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 810 Sq Ft
      • Built 1962
      7413 Poplar Ave, Chestertown, MD 21620

      Last Sold Summary

      • 34% Above List Price
      • $163/SF
      • 4 Days On Market
      • Last Sold Price $132,000
      • Sep 06, 2023

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • /73

      Est $617,146

      Not Listed For Sale

      6270 Quaker Neck Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,400 Sq Ft
      • Built 2011
      6270 Quaker Neck Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9% Below List Price
      • $281/SF
      • 27 Days On Market
      • Last Sold Price $675,000
      • Nov 26, 2024

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    • /37

      Est $655,704

      Not Listed For Sale

      7775 Waterview Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 1937
      7775 Waterview Ln, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $351/SF
      • 81 Days On Market
      • Last Sold Price $625,000
      • Jan 02, 2025

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    • /13

      Est $333,425

      Not Listed For Sale

      24745 Langford Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,600 Sq Ft
      • Built 1961
      24745 Langford Rd, Chestertown, MD 21620

      Last Sold Summary

      • 42% Above List Price
      • $146/SF
      • 6 Days On Market
      • Last Sold Price $234,000
      • Aug 25, 2023

      Last Listing Agent Shannon Thayer Douglas Realty, LLC

Showing Results 521 - 560, Page 14 of 18

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