198

Recently Sold Chestertown, MD Homes

Section Image
  • 101 Metcalfe Rd, Chestertown, MD 21620
    101 Metcalfe Rd, Chestertown, MD 21620
    101 Metcalfe Rd, Chestertown, MD 21620
    /26

    $264,900 Sold Dec 05, 2025

    101 Metcalfe Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2025

    Last Sold Summary

    • $207/SF
    • 2 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    101 Metcalfe Rd, Chestertown, MD 21620
  • 109 Grant Ct, Chestertown, MD 21620
    109 Grant Ct, Chestertown, MD 21620
    109 Grant Ct, Chestertown, MD 21620
    /38

    $389,900 Sold Feb 06, 2025

    109 Grant Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2021

    Last Sold Summary

    • $290/SF
    • 40 Days On Market

    Current Estimated Value $395,582

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    109 Grant Ct, Chestertown, MD 21620
  • 125 Primrose Rd, Chestertown, MD 21620
    125 Primrose Rd, Chestertown, MD 21620
    125 Primrose Rd, Chestertown, MD 21620
    /48

    $350,000 Sold Dec 30, 2024

    125 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,102 Sq Ft
    • Built 1976

    Last Sold Summary

    • $167/SF
    • 50 Days On Market

    Current Estimated Value $358,677

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    125 Primrose Rd, Chestertown, MD 21620
  • 116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    116 Oak Leaf Dr, Chestertown, MD 21620
    /38

    $289,500 Sold May 05, 2025

    116 Oak Leaf Dr, Chestertown, MD 21620

    • 2 Beds
    • 4 Baths
    • 1,867 Sq Ft
    • Built 2004

    Last Sold Summary

    • $155/SF
    • 13 Days On Market

    Current Estimated Value $298,455

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    116 Oak Leaf Dr, Chestertown, MD 21620
  • 21363 Indiana Ave, Chestertown, MD 21620
    21363 Indiana Ave, Chestertown, MD 21620
    21363 Indiana Ave, Chestertown, MD 21620
    /24

    $280,000 Sold Aug 07, 2025

    21363 Indiana Ave, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 10 Days On Market

    Current Estimated Value $274,766

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 21620
  • 0 Elm Rd, Chestertown, MD 21620
    0 Elm Rd, Chestertown, MD 21620
    /2

    $14,000 Sold Sep 05, 2025

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 0.22 Acre
    • $63,636 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    0 Elm Rd, Chestertown, MD 21620
  • 517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    517 High St, Chestertown, MD 21620
    /51

    $361,500 Sold Dec 19, 2025

    517 High St, Chestertown, MD 21620

    • Studio
    • 1,728 Sq Ft
    • Built 1900

    Last Sold Summary

    • $209/SF
    • 51 Days On Market

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

    517 High St, Chestertown, MD 21620
  • 24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    24576 Langford Rd, Chestertown, MD 21620
    /60

    $725,000 Sold Aug 05, 2025

    24576 Langford Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft
    • Built 1989

    Last Sold Summary

    • $180/SF
    • 134 Days On Market

    Current Estimated Value $703,932

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
  • 0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
    /2

    $75,000 Sold Sep 26, 2025

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620

    • Land
    • 1.49 Acres
    • $50,336 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
  • 225 Duke of Kent St, Chestertown, MD 21620
    225 Duke of Kent St, Chestertown, MD 21620
    225 Duke of Kent St, Chestertown, MD 21620
    /34

    $395,000 Sold Nov 10, 2025

    225 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2000

    Last Sold Summary

    • $214/SF
    • 16 Days On Market

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
  • 23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    23393 Cacaway Farm Ln, Chestertown, MD 21620
    /45

    $1,150,000 Sold Dec 10, 2025

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft
    • Built 1990

    Last Sold Summary

    • $259/SF
    • 361 Days On Market

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
  • 21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    21317 Persimmon Dr, Chestertown, MD 21620
    /31

    $191,000 Sold Oct 03, 2025

    21317 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,269 Sq Ft
    • Built 1955

    Last Sold Summary

    • $151/SF
    • 67 Days On Market

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
  • 101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    101 S Mill St, Chestertown, MD 21620
    /22

    $490,000 Sold May 21, 2025

    101 S Mill St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft
    • Built 1900

    Last Sold Summary

    • $332/SF
    • 14 Days On Market

    Current Estimated Value $490,562

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • 10050 Forrest Ln, Chestertown, MD 21620
    10050 Forrest Ln, Chestertown, MD 21620
    10050 Forrest Ln, Chestertown, MD 21620
    /49

    $905,000 Sold Nov 14, 2025

    10050 Forrest Ln, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1993

    Last Sold Summary

    • $497/SF
    • 4 Days On Market

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /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 $123,526

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    205 River Rd, Chestertown, MD 21620
  • 106 Silver Heel Rd, Chestertown, MD 21620
    106 Silver Heel Rd, Chestertown, MD 21620
    106 Silver Heel Rd, Chestertown, MD 21620
    /43

    $355,000 Sold Jan 10, 2025

    106 Silver Heel Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,672 Sq Ft
    • Built 2023

    Last Sold Summary

    • $212/SF
    • 0 Days On Market

    Current Estimated Value $365,820

    Last Listing Agent Chuck Zepp EXP Realty, LLC

    106 Silver Heel Rd, Chestertown, MD 21620
  • 10761 Kasota Rd, Chestertown, MD 21620
    10761 Kasota Rd, Chestertown, MD 21620
    10761 Kasota Rd, Chestertown, MD 21620
    /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

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
  • 313 S Queen St, Chestertown, MD 21620
    313 S Queen St, Chestertown, MD 21620
    313 S Queen St, Chestertown, MD 21620
    /57

    $427,000 Sold Jan 29, 2025

    313 S Queen St, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 1,995 Sq Ft
    • Built 1997

    Last Sold Summary

    • $214/SF
    • 1 Day On Market

    Current Estimated Value $459,907

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    313 S Queen St, Chestertown, MD 21620
  • 130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    /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 $440,372

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    130 Sheaffer Rd, Chestertown, MD 21620
  • 127 Char Nor Manor Blvd, Chestertown, MD 21620
    127 Char Nor Manor Blvd, Chestertown, MD 21620
    127 Char Nor Manor Blvd, Chestertown, MD 21620
    /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

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

    127 Char Nor Manor Blvd, Chestertown, MD 21620
  • 103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    103 Adela Way, Chestertown, MD 21620
    /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

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
  • 10670 Tintah Rd, Chestertown, MD 21620
    10670 Tintah Rd, Chestertown, MD 21620
    10670 Tintah Rd, Chestertown, MD 21620
    /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 $297,694

    Last Listing Agent Bronwyn Scott Samson Properties

    10670 Tintah Rd, Chestertown, MD 21620
  • 107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    107 Dutchess Rd, Chestertown, MD 21620
    /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 $307,597

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess 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
  • 10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    10705 Millbrook Dr, Chestertown, MD 21620
    /73

    $380,000 Sold Jul 30, 2025

    10705 Millbrook Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft
    • Built 1988

    Last Sold Summary

    • $180/SF
    • 11 Days On Market

    Current Estimated Value $374,044

    Last Listing Agent Adam Murphy RE/MAX Realty Centre, Inc.

    10705 Millbrook 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 25195 Lovers Ln, Chestertown, MD 21620
    25195 Lovers Ln, Chestertown, MD 21620
    /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

    Last Listing Agent William Norris Select Land & Homes, LLC

    25195 Lovers Ln, 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

Showing Results 161 - 198, Page 5 of 5

Maryland Kent County Chestertown

Recently Sold Real Estate & Homes in Chestertown, MD

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