6,886

Chestertown, MD Homes

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  • /2

    $119,500 Sold Jun 26, 2025

    205 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $118,317 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $122,426

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    205 River Rd, Chestertown, MD 21620
    • /45

      Est $331,194 Not Listed For Sale

      212 Rolling Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,148 Sq Ft
      • Built 1969
      212 Rolling Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $279/SF
      • 13 Days On Market

      Last Sold Price $320,000

      Last Listing Agent Roxana Tapia Long & Foster

  • /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 $871,795

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
    • /26

      Est $327,975 Not Listed For Sale

      8890 Fairlee Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 2017
      8890 Fairlee Rd, Chestertown, MD 21620

      Last Sold Summary

      • 20% Above List Price
      • $222/SF
      • 3 Days On Market

      Last Sold Price $273,250

      Last Listing Agent Joelle Dolch Cross Street Realtors LLC

  • /25

    $431,000 Sold Apr 22, 2025

    130 Sheaffer Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,766 Sq Ft
    • Built 1999

    Last Sold Summary

    • $244/SF
    • 1 Day On Market

    Current Estimated Value $449,082

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    130 Sheaffer Rd, Chestertown, MD 21620
    • /51

      Est $1,063,776 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

      • 23% Above List Price
      • $285/SF
      • 106 Days On Market

      Last Sold Price $865,000

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /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 $355,705

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

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

      Est $342,867 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

      • 5% Above List Price
      • $137/SF
      • 18 Days On Market

      Last Sold Price $325,000

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • /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 $581,684

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
    • /54

      Est $703,233 Not Listed For Sale

      25300 Foxchase Dr, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,832 Sq Ft
      • Built 1999
      25300 Foxchase Dr, Chestertown, MD 21620

      Last Sold Summary

      • 28% Above List Price
      • $194/SF
      • 5 Days On Market

      Last Sold Price $550,000

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /29

    $296,500 Sold Jul 25, 2025

    10670 Tintah Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1999

    Last Sold Summary

    • $211/SF
    • 11 Days On Market

    Current Estimated Value $299,890

    Last Listing Agent Bronwyn Scott Samson Properties

    10670 Tintah Rd, Chestertown, MD 21620
    • /24

      Est $314,859 Not Listed For Sale

      22974 Bay Shore Rd, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,440 Sq Ft
      • Built 1920
      22974 Bay Shore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $191/SF
      • 11 Days On Market

      Last Sold Price $275,000

      Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

  • /23

    $290,000 Sold Aug 13, 2025

    107 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 2005

    Last Sold Summary

    • $210/SF
    • 234 Days On Market

    Current Estimated Value $313,333

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
    • /59

      Est $1,566,870 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

      • 8% Above List Price
      • $383/SF
      • 4 Days On Market

      Last Sold Price $1,450,000

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /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 $682,811

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
    • /30

      Est $435,198 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

      • 9% Above List Price
      • $215/SF
      • 4 Days On Market

      Last Sold Price $398,000

      Last Listing Agent Carol Tinnin RE/MAX

  • /23

    $352,500 Sold Apr 30, 2025

    505 N Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,402 Sq Ft
    • Built 1985

    Last Sold Summary

    • $251/SF
    • 9 Days On Market

    Current Estimated Value $373,347

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    505 N Kent St, Chestertown, MD 21620
    • /52

      Est $666,982 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

      • 11% Above List Price
      • $221/SF
      • 4 Days On Market

      Last Sold Price $599,000

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • /29

    $380,000 Sold Mar 14, 2025

    409 Riverview Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • Built 1998

    Last Sold Summary

    • $211/SF
    • 118 Days On Market

    Current Estimated Value $397,665

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    409 Riverview Rd, Chestertown, MD 21620
    • /29

      Est $672,511 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

      • 12% Above List Price
      • $225/SF
      • 155 Days On Market

      Last Sold Price $600,000

      Last Listing Agent Paula Ruckelshaus Long & Foster

  • /2

    $680,000 Sold Aug 08, 2025

    100 Little Harbor Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 2015

    Last Sold Summary

    • $309/SF
    • 82 Days On Market

    Current Estimated Value $695,197

    Last Listing Agent Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
    • /24

      Est $418,358 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

      • 57% Above List Price
      • $128/SF
      • 3 Days On Market

      Last Sold Price $267,250

      Last Listing Agent Stacy Kendall Cross Street Realtors LLC

  • /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 $398,531

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
    • /29

      Est $911,784 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

      • 5% Above List Price
      • $466/SF
      • 25 Days On Market

      Last Sold Price $865,000

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • /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 $359,671

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
    • /37

      Est $373,351 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

      Last Listing Agent Brenda Fornos Taylor Properties

  • /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 $257,568

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620
    • /22

      Est $269,983 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

      • 14% Above List Price
      • $223/SF
      • 71 Days On Market

      Last Sold Price $237,000

      Last Listing Agent Robin Fithian Rock Hall Properties

  • /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 $1,106,683

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, Chestertown, MD 21620
    • /41

      Est $428,713 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

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /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 $510,760

    Last Listing Agent Heather Branham The Parker Group

    314 Devon Dr, Chestertown, MD 21620
    • /57

      Est $573,587 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

      • 34% Above List Price
      • $214/SF
      • 1 Day On Market

      Last Sold Price $427,000

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /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 $1,126,766

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
    • /45

      Est $498,230 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

      • 78% Above List Price
      • $150/SF
      • 22 Days On Market

      Last Sold Price $280,000

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • /87

    $440,000 Sold Mar 13, 2025

    312 Princess Anne Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 1,848 Sq Ft
    • Built 1987

    Last Sold Summary

    • $238/SF
    • 31 Days On Market

    Current Estimated Value $429,347

    Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

    312 Princess Anne Dr, Chestertown, MD 21620
    • /30

      Est $427,505 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

      • 11% Above List Price
      • $299/SF
      • 2 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /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 $773,685

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    109 S Water St, Chestertown, MD 21620
    • /43

      Est $246,089 Not Listed For Sale

      21217 Texas Ave, Chestertown, MD 21620

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft
      • Built 1952
      21217 Texas Ave, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $236/SF
      • 23 Days On Market

      Last Sold Price $215,000

      Last Listing Agent Terry Catalano RE/MAX

  • /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 $297,538

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10141 Flatland Rd, Chestertown, MD 21620
    • /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

Showing Results 481 - 520, Page 13 of 18

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