Recently Sold Chestertown, MD Homes

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  /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
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  /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
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  /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
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  /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 $307,296

  Last Listing Agent LAURIE KREIDER Realty ONE Group Unlimited

  7425 Wilkins Ln, Chestertown, MD 21620
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  /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
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  /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
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  /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 $345,625

  Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

  121 Primrose Rd, Chestertown, MD 21620
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  /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
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  $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

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