207

Recently Sold Homes in 21620

Section Image
  • 109 Edmore Rd, Chestertown, MD 21620
    109 Edmore Rd, Chestertown, MD 21620
    109 Edmore Rd, Chestertown, MD 21620
    /24

    $344,900 Sold Jun 25, 2025

    109 Edmore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1993

    Last Sold Summary

    • $257/SF
    • 24 Days On Market

    Current Estimated Value $350,782

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
  • 114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    114 Darden Rd, Chestertown, MD 21620
    /33

    $270,000 Sold Aug 25, 2025

    114 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1978

    Last Sold Summary

    • $256/SF
    • 72 Days On Market

    Current Estimated Value $279,833

    Last Listing Agent Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
  • 110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    110 Philosophers Terrace, Chestertown, MD 21620
    /22

    $175,000 Sold Jul 25, 2025

    110 Philosophers Terrace, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft
    • Built 1955

    Last Sold Summary

    • $195/SF
    • 85 Days On Market

    Current Estimated Value $202,904

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
  • 206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    206 Valley Rd, Chestertown, MD 21620
    /37

    $590,000 Sold Jan 12, 2026

    206 Valley Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft
    • Built 1957

    Last Sold Summary

    • $206/SF
    • 27 Days On Market

    Current Estimated Value $597,376

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
  • 206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    206 Silver Heel Dr, Chestertown, MD 21620
    /36

    $375,000 Sold Aug 13, 2025

    206 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,302 Sq Ft
    • Built 2022

    Last Sold Summary

    • $163/SF
    • 1 Day On Market

    Last Listing Agent TJ Bennett Samson Properties

    206 Silver Heel Dr, Chestertown, MD 21620
  • 7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    7961 Quaker Neck Rd, Chestertown, MD 21620
    /93

    $1,550,000 Sold Nov 07, 2025

    7961 Quaker Neck Rd, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft
    • Built 1952

    Last Sold Summary

    • $372/SF
    • 150 Days On Market

    Current Estimated Value $1,522,222

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
  • 23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    23620 Lands End Rd, Chestertown, MD 21620
    /77

    $4,221,800 Sold Nov 24, 2025

    23620 Lands End Rd, Chestertown, MD 21620

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft
    • Built 2001

    Last Sold Summary

    • $429/SF
    • 219 Days On Market

    Current Estimated Value $4,199,087

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • 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
  • 217 Philosophers Terrace, Chestertown, MD 21620
    217 Philosophers Terrace, Chestertown, MD 21620
    /2

    $370,000 Sold May 01, 2026

    217 Philosophers Terrace, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • Built 1950

    Last Sold Summary

    • 14% Above List Price
    • $264/SF
    • 3 Days On Market

    Current Estimated Value $363,243

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    217 Philosophers Terrace, 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
    • 9,583 Sq Ft
    • $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
  • 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 $277,950

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, 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

    Current Estimated Value $368,255

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

    517 High St, Chestertown, MD 21620
  • 515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    515 N Kent St, Chestertown, MD 21620
    /36

    $495,000 Sold Apr 17, 2026

    515 N Kent St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • Built 1965

    Last Sold Summary

    • $223/SF
    • 1 Day On Market

    Current Estimated Value $489,071

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    515 N Kent 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 $735,196

    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

    Current Estimated Value $405,173

    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

    Current Estimated Value $1,085,728

    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

    Current Estimated Value $189,885

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
  • 165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    165 Char Nor Manor Blvd, Chestertown, MD 21620
    /67

    $424,000 Sold Jan 30, 2026

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft
    • Built 2006

    Last Sold Summary

    • $188/SF
    • 159 Days On Market

    Current Estimated Value $445,046

    Last Listing Agent Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, 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 $501,928

    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

    Current Estimated Value $904,566

    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 $518,136

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    205 River 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

    Current Estimated Value $906,818

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota 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

    Current Estimated Value $360,567

    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

    Current Estimated Value $586,276

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
  • 10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    10751 Millbrook Dr, Chestertown, MD 21620
    /50

    $350,000 Sold Mar 27, 2026

    10751 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft
    • Built 1975

    Last Sold Summary

    • $180/SF
    • 175 Days On Market

    Current Estimated Value $351,182

    Last Listing Agent Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, 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 $303,030

    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 $316,474

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
  • 200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    200 Washington Ave, Chestertown, MD 21620
    /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 $687,187

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, 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 $380,872

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

    10705 Millbrook Dr, 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 $695,262

    Last Listing Agent Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
  • 112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    112 Metcalf Rd, Chestertown, MD 21620
    /54

    $250,000 Sold Apr 10, 2026

    112 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2023

    Last Sold Summary

    • $195/SF
    • 36 Days On Market

    Current Estimated Value $250,379

    Last Listing Agent April Heim Rosendale Realty

    112 Metcalf Rd, 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

    Current Estimated Value $402,765

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
  • 303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    303 E Campus Ave, Chestertown, MD 21620
    /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 $354,816

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
  • 7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    7521 Pine Ave, Chestertown, MD 21620
    /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 $249,390

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620
  • 206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    206 Cannon St, Chestertown, MD 21620
    /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 $1,100,039

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, 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 $515,988

    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 $1,145,443

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    22153 1st Point Rd, Chestertown, MD 21620
  • 104 Garland Ave, Chestertown, MD 21620
    104 Garland Ave, Chestertown, MD 21620
    104 Garland Ave, Chestertown, MD 21620
    /34

    $480,000 Sold Apr 17, 2026

    104 Garland Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft
    • Built 2005

    Last Sold Summary

    • 9% Above List Price
    • $277/SF
    • 9 Days On Market

    Current Estimated Value $410,197

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    104 Garland Ave, Chestertown, MD 21620
  • 109 S Water St, Chestertown, MD 21620
    109 S Water St, Chestertown, MD 21620
    109 S Water St, Chestertown, MD 21620
    /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 $738,295

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    109 S Water St, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 6

Maryland Kent County Chestertown 21620

Recently Sold Real Estate & Homes in 21620

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