6,869

Chestertown, MD Homes

Section Image
    • 10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      10355 Bunting Rd, Chestertown, MD 21620
      /17

      Est $275,781 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft

      10355 Bunting Rd, Chestertown, MD 21620

      10355 Bunting Rd, Chestertown, MD 21620
  • 505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    /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 $361,191

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    505 N Kent St, Chestertown, MD 21620
    • 225 Richard Dr, Chestertown, MD 21620
      225 Richard Dr, Chestertown, MD 21620
      225 Richard Dr, Chestertown, MD 21620
      /38

      Est $593,769 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,749 Sq Ft

      225 Richard Dr, Chestertown, MD 21620

      225 Richard Dr, Chestertown, MD 21620
  • 409 Riverview Rd, Chestertown, MD 21620
    409 Riverview Rd, Chestertown, MD 21620
    409 Riverview Rd, Chestertown, MD 21620
    /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 $388,130

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    409 Riverview Rd, Chestertown, MD 21620
    • 23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      23240 Clarissa Rd, Chestertown, MD 21620
      /21

      Est $310,498 Not Listed For Sale

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

      23240 Clarissa Rd, Chestertown, MD 21620

      23240 Clarissa Rd, Chestertown, MD 21620
  • 100 Little Harbor Way, Chestertown, MD 21620
    100 Little Harbor Way, Chestertown, MD 21620
    /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 $683,785

    Last Listing Agent Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
    • 306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      306 Roosevelt Dr, Chestertown, MD 21620
      /20

      Est $261,407 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,152 Sq Ft

      306 Roosevelt Dr, Chestertown, MD 21620

      306 Roosevelt Dr, Chestertown, MD 21620
  • 221 Richard Dr, Chestertown, MD 21620
    221 Richard Dr, Chestertown, MD 21620
    221 Richard Dr, Chestertown, MD 21620
    /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

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $298,078 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft

      27370 Morgnec Rd, Chestertown, MD 21620

      27370 Morgnec Rd, Chestertown, MD 21620
  • 314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    314 Devon Dr, Chestertown, MD 21620
    /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 $490,964

    Last Listing Agent Heather Branham The Parker Group

    314 Devon Dr, 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 $566,500 Not Listed For Sale

      • 4 Beds
      • 2 Baths
      • 2,004 Sq Ft

      223 S Queen St, Chestertown, MD 21620

      223 S Queen St, Chestertown, MD 21620
  • 22153 1st Point Rd, Chestertown, MD 21620
    22153 1st Point Rd, Chestertown, MD 21620
    22153 1st Point Rd, Chestertown, MD 21620
    /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 $1,066,501

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
    • 1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      1005 Twin Ct, Chestertown, MD 21620
      /18

      Est $389,392 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,854 Sq Ft

      1005 Twin Ct, Chestertown, MD 21620

      1005 Twin Ct, Chestertown, MD 21620
  • 312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    312 Princess Anne Dr, Chestertown, MD 21620
    /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 $421,407

    Last Listing Agent Jim Davidson Coldwell Banker Waterman Realty

    312 Princess Anne Dr, 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 $305,297 Not Listed For Sale

      • 3 Beds
      • 1 Bath
      • 1,456 Sq Ft

      9769 Augustine Herman Hwy, Chestertown, MD 21620

      9769 Augustine Herman Hwy, Chestertown, MD 21620
  • 117 Primrose Rd, Chestertown, MD 21620
    117 Primrose Rd, Chestertown, MD 21620
    117 Primrose Rd, Chestertown, MD 21620
    /15

    $325,000 Sold Feb 27, 2025

    117 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,460 Sq Ft
    • Built 1972

    Last Sold Summary

    • $132/SF
    • 112 Days On Market

    Current Estimated Value $339,943

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    117 Primrose Rd, Chestertown, MD 21620
    • 106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      106 Devon Dr, Chestertown, MD 21620
      /43

      Est $413,559 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft

      106 Devon Dr, Chestertown, MD 21620

      106 Devon Dr, Chestertown, MD 21620
  • 10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    /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 $292,761

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10141 Flatland Rd, Chestertown, MD 21620
    • 212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      212 Rolling Rd, Chestertown, MD 21620
      /45

      Est $333,335 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,148 Sq Ft

      212 Rolling Rd, Chestertown, MD 21620

      212 Rolling Rd, Chestertown, MD 21620
  • 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 $304,731

    Last Listing Agent LAURIE KREIDER Realty ONE Group Unlimited

    7425 Wilkins Ln, Chestertown, MD 21620
    • 5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      5598 Langford Bay Rd, Chestertown, MD 21620
      /31

      Est $819,722 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,736 Sq Ft

      5598 Langford Bay Rd, Chestertown, MD 21620

      5598 Langford Bay Rd, Chestertown, MD 21620
  • 420 Cannon St, Chestertown, MD 21620
    420 Cannon St, Chestertown, MD 21620
    420 Cannon St, Chestertown, MD 21620
    /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 $352,085

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    420 Cannon St, Chestertown, MD 21620
    • 8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      8890 Fairlee Rd, Chestertown, MD 21620
      /26

      Est $316,918 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      8890 Fairlee Rd, Chestertown, MD 21620

      8890 Fairlee Rd, Chestertown, MD 21620
  • 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
    • 109 N Water St, Chestertown, MD 21620
      109 N Water St, Chestertown, MD 21620
      109 N Water St, Chestertown, MD 21620
      /51

      Est $1,046,460 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 3,030 Sq Ft

      109 N Water St, Chestertown, MD 21620

      109 N Water St, Chestertown, MD 21620
  • 23315 Sandpiper Rd, Chestertown, MD 21620
    23315 Sandpiper Rd, Chestertown, MD 21620
    23315 Sandpiper Rd, Chestertown, MD 21620
    /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 $303,102

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    23315 Sandpiper Rd, Chestertown, MD 21620
    • 25300 Foxchase Dr, Chestertown, MD 21620
      25300 Foxchase Dr, Chestertown, MD 21620
      25300 Foxchase Dr, Chestertown, MD 21620
      /54

      Est $684,648 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,832 Sq Ft

      25300 Foxchase Dr, Chestertown, MD 21620

      25300 Foxchase Dr, Chestertown, MD 21620
    • 22974 Bay Shore Rd, Chestertown, MD 21620
      22974 Bay Shore Rd, Chestertown, MD 21620
      22974 Bay Shore Rd, Chestertown, MD 21620
      /24

      Est $312,819 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,440 Sq Ft

      22974 Bay Shore Rd, Chestertown, MD 21620

      22974 Bay Shore Rd, Chestertown, MD 21620
    • 1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      1 Reed Ct, Chestertown, MD 21620
      /30

      Est $433,307 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,854 Sq Ft

      1 Reed Ct, Chestertown, MD 21620

      1 Reed Ct, Chestertown, MD 21620
    • 8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      8623 Orchard Dr, Chestertown, MD 21620
      /52

      Est $636,502 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,708 Sq Ft

      8623 Orchard Dr, Chestertown, MD 21620

      8623 Orchard Dr, Chestertown, MD 21620
    • 23795 Lands End Rd, Chestertown, MD 21620
      23795 Lands End Rd, Chestertown, MD 21620
      23795 Lands End Rd, Chestertown, MD 21620
      /24

      Est $364,210 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 2,088 Sq Ft

      23795 Lands End Rd, Chestertown, MD 21620

      23795 Lands End Rd, Chestertown, MD 21620
    • 123 High St, Chestertown, MD 21620
      123 High St, Chestertown, MD 21620
      123 High St, Chestertown, MD 21620
      /29

      Est $904,206 Not Listed For Sale

      • 3 Beds
      • 3 Baths
      • 1,855 Sq Ft

      123 High St, Chestertown, MD 21620

      123 High St, Chestertown, MD 21620
    • 9062 Fairlee Rd, Chestertown, MD 21620
      9062 Fairlee Rd, Chestertown, MD 21620
      9062 Fairlee Rd, Chestertown, MD 21620
      /37

      Est $373,004 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft

      9062 Fairlee Rd, Chestertown, MD 21620

      9062 Fairlee Rd, Chestertown, MD 21620
    • 21239 Kansas Ave, Chestertown, MD 21620
      21239 Kansas Ave, Chestertown, MD 21620
      21239 Kansas Ave, Chestertown, MD 21620
      /22

      Est $257,062 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 1,064 Sq Ft

      21239 Kansas Ave, Chestertown, MD 21620

      21239 Kansas Ave, Chestertown, MD 21620
    • 214 Richard Dr, Chestertown, MD 21620
      214 Richard Dr, Chestertown, MD 21620
      214 Richard Dr, Chestertown, MD 21620
      /41

      Est $409,207 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,723 Sq Ft

      214 Richard Dr, Chestertown, MD 21620

      214 Richard Dr, Chestertown, MD 21620
    • 412 High St, Chestertown, MD 21620
      412 High St, Chestertown, MD 21620
      412 High St, Chestertown, MD 21620
      /45

      Est $473,586 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,867 Sq Ft

      412 High St, Chestertown, MD 21620

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

      Est $402,894 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,288 Sq Ft

      529 Cannon St, Chestertown, MD 21620

      529 Cannon St, Chestertown, MD 21620
    • 25731 Collins Ave, Chestertown, MD 21620
      25731 Collins Ave, Chestertown, MD 21620
      25731 Collins Ave, Chestertown, MD 21620
      /53

      Est $848,890 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,751 Sq Ft

      25731 Collins Ave, Chestertown, MD 21620

      25731 Collins Ave, Chestertown, MD 21620
    • 21217 Texas Ave, Chestertown, MD 21620
      21217 Texas Ave, Chestertown, MD 21620
      21217 Texas Ave, Chestertown, MD 21620
      /43

      Est $228,941 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 912 Sq Ft

      21217 Texas Ave, Chestertown, MD 21620

      21217 Texas Ave, Chestertown, MD 21620
    • 813 S Meadowview Dr, Chestertown, MD 21620
      813 S Meadowview Dr, Chestertown, MD 21620
      813 S Meadowview Dr, Chestertown, MD 21620
      /35

      Est $423,550 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,509 Sq Ft

      813 S Meadowview Dr, Chestertown, MD 21620

      813 S Meadowview Dr, Chestertown, MD 21620

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