6,886

Chestertown, MD Homes

Section Image
    • /35

      Est $443,203 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

      • 9% Above List Price
      • $269/SF
      • 3 Days On Market

      Last Sold Price $406,000

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /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 $348,964

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    420 Cannon St, Chestertown, MD 21620
    • /31

      Est $286,926 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

      • 2% Above List Price
      • $233/SF
      • 4 Days On Market

      Last Sold Price $280,000

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

  • /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
    • /50

      Est $365,084 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

      • 16% Above List Price
      • $175/SF
      • 96 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Joseph Ciganek 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 $342,468

    Last Listing Agent William Norris Select Land & Homes, LLC

    25195 Lovers Ln, Chestertown, MD 21620
    • /41

      Est $411,703 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

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • /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 $311,739

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    23315 Sandpiper Rd, Chestertown, MD 21620
    • /48

      Est $272,790 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

      • 5% Above List Price
      • $226/SF
      • 263 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    • /57

      Est $856,388 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

      • 16% Above List Price
      • $487/SF
      • 8 Days On Market

      Last Sold Price $740,000

      Last Listing Agent Tammy Studebaker EXP Realty, LLC

    • /22

      Est $535,875 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

      • 9% Above List Price
      • $236/SF
      • 129 Days On Market

      Last Sold Price $492,000

      Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    • /33

      Est $327,326 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

      • 17% Above List Price
      • $211/SF
      • 9 Days On Market

      Last Sold Price $279,900

      Last Listing Agent David Moore Real Broker, LLC

    • /20

      Est $329,000 Not Listed For Sale

      8220 Airy Hill Rd, Chestertown, MD 21620

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

      Last Sold Summary

      • 9% Below List Price
      • $304/SF
      • 94 Days On Market

      Last Sold Price $360,000

      Last Listing Agent Sarah King Cross Street Realtors LLC

    • /23

      Est $251,725 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

      • 9% Above List Price
      • $181/SF
      • 12 Days On Market

      Last Sold Price $232,000

      Last Listing Agent Jordan Larigan LPT Realty, LLC

    • /41

      Est $465,092 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

      • 24% Above List Price
      • $177/SF
      • 1 Day On Market

      Last Sold Price $375,000

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    • /85

      Est $1,832,317 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

      • 8% Below List Price
      • $509/SF
      • 3 Days On Market

      Last Sold Price $2,000,000

      Last Listing Agent Richard Budden Coldwell Banker Chesapeake Real Estate Company

    • /13

      Est $439,775 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

      • 26% Above List Price
      • $163/SF
      • 12 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Aaron Butler Real Estate Consultants

    • /24

      Est $336,389 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

      • 12% Above List Price
      • $233/SF
      • 30 Days On Market

      Last Sold Price $299,900

      Last Listing Agent Lona Todd Taylor Properties

    • /19

      Est $277,071 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

      • 14% Above List Price
      • $213/SF
      • 1 Day On Market

      Last Sold Price $242,500

      Last Listing Agent Lori Sample EXIT Preferred Realty

    • /11

      Est $175,237 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

      • 33% Above List Price
      • $163/SF
      • 4 Days On Market

      Last Sold Price $132,000

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • /73

      Est $641,632 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

      • 5% Below List Price
      • $281/SF
      • 27 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    • /37

      Est $643,737 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

      • 3% Above List Price
      • $351/SF
      • 81 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    • /13

      Est $324,357 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

      • 39% Above List Price
      • $146/SF
      • 6 Days On Market

      Last Sold Price $234,000

      Last Listing Agent Shannon Thayer Douglas Realty, LLC

    • /19

      Est $235,993 Not Listed For Sale

      6292 Broad Neck Rd, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 1,150 Sq Ft
      • Built 1900
      6292 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 178% Above List Price
      • $74/SF
      • 18 Days On Market

      Last Sold Price $85,000

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    • /68

      Est $1,294,989 Not Listed For Sale

      22770 Fairgale Farm Ln, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,535 Sq Ft
      • Built 1999
      22770 Fairgale Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $503/SF
      • 98 Days On Market

      Last Sold Price $1,275,000

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    • /32

      Est $349,955 Not Listed For Sale

      22939 Bay Shore Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,505 Sq Ft
      • Built 1999
      22939 Bay Shore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $215/SF
      • 3 Days On Market

      Last Sold Price $324,000

      Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    • /82

      Est $1,361,649 Not Listed For Sale

      22956 Fairgale Farm Ln, Chestertown, MD 21620

      • 5 Beds
      • 4.5 Baths
      • 6,459 Sq Ft
      • Built 2000
      22956 Fairgale Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 13% Above List Price
      • $186/SF
      • 119 Days On Market

      Last Sold Price $1,200,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    • /33

      Est $367,110 Not Listed For Sale

      23055 Parsons Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,473 Sq Ft
      • Built 1965
      23055 Parsons Rd, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $223/SF
      • 35 Days On Market

      Last Sold Price $329,000

      Last Listing Agent Sharon Clark Clark & Co Realty, LLC

    • /32

      Est $369,884 Not Listed For Sale

      24349 Chestertown Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,327 Sq Ft
      • Built 1962
      24349 Chestertown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13% Above List Price
      • $246/SF
      • 2 Days On Market

      Last Sold Price $326,100

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    • /13

      Est $240,028 Not Listed For Sale

      8842 Fairlee Rd, Chestertown, MD 21620

      • Built 1960
      8842 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $175/SF
      • 7 Days On Market

      Last Sold Price $221,000

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    • /7

      Est $106,967 Not Listed For Sale

      23060 Old Fairlee Rd, Chestertown, MD 21620

      • Studio
      • 1,040 Sq Ft
      • Built 1900
      23060 Old Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 138% Above List Price
      • $43/SF
      • 210 Days On Market

      Last Sold Price $45,000

      Last Listing Agent Julia Hilfiker Gunther-McClary Real Estate

    • /23

      Est $325,722 Not Listed For Sale

      9096 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,104 Sq Ft
      • Built 1900
      9096 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Below List Price
      • $322/SF
      • 4 Days On Market

      Last Sold Price $355,500

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • /17

      Est $269,869 Not Listed For Sale

      8899 Georgetown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 966 Sq Ft
      • Built 1968
      8899 Georgetown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $243/SF
      • 75 Days On Market

      Last Sold Price $235,000

      Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    • /8

      Not Listed For Sale

      22532 Tolchester Beach Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,696 Sq Ft
      • Built 1920
      22532 Tolchester Beach Rd, Chestertown, MD 21620

      Last Sold Summary

      • 156% Above List Price
      • $44/SF
      • 35 Days On Market

      Last Sold Price $74,900

      Last Listing Agent Matthew Altizer ANR Realty, LLC

    • /34

      Est $517,975 Not Listed For Sale

      9816 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,624 Sq Ft
      • Built 1970
      9816 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 4% Above List Price
      • $307/SF
      • 39 Days On Market

      Last Sold Price $499,000

      Last Listing Agent Jennifer Thomas RE/MAX

    • /28

      Est $400,817 Not Listed For Sale

      10630 Club Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,844 Sq Ft
      • Built 1963
      10630 Club Rd, Chestertown, MD 21620

      Last Sold Summary

      • 25% Above List Price
      • $174/SF
      • 6 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Beth Green Doug Ashley Realtors, LLC

    • /44

      Est $276,960 Not Listed For Sale

      8970 Cumberland St, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1945
      8970 Cumberland St, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $225/SF
      • 4 Days On Market

      Last Sold Price $240,000

      Last Listing Agent Jonathan Scheffenacker Redfin Corp

    • /13

      Est $328,044 Not Listed For Sale

      8900 Fairlee Rd, Chestertown, MD 21620

      • Studio
      • 2,188 Sq Ft
      • Built 1900
      8900 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 55% Above List Price
      • $97/SF
      • 76 Days On Market

      Last Sold Price $212,000

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    • /21

      Est $274,060 Not Listed For Sale

      23073 Parsons Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,792 Sq Ft
      • Built 1900
      23073 Parsons Rd, Chestertown, MD 21620

      Last Sold Summary

      • 25% Above List Price
      • $123/SF
      • 47 Days On Market

      Last Sold Price $220,000

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

    • /29

      Est $304,854 Not Listed For Sale

      21199 Iowa Ave, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,566 Sq Ft
      • Built 2003
      21199 Iowa Ave, Chestertown, MD 21620

      Last Sold Summary

      • 12% Below List Price
      • $220/SF
      • 28 Days On Market

      Last Sold Price $345,000

      Last Listing Agent Thomas Huston Real Broker LLC

Showing Results 521 - 560, Page 14 of 18

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