6,896

Chestertown, MD Homes

Section Image
  • /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 $1,091,007

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
    • /25

      Est $340,710

      Not Listed For Sale

      8489 Broad Neck Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,464 Sq Ft
      • Built 1960
      8489 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 14% Above List Price
      • $205/SF
      • 10 Days On Market
      • Last Sold Price $299,900
      • Nov 01, 2024

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /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
    • /17

      Est $281,930

      Not Listed For Sale

      10355 Bunting Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 2002
      10355 Bunting Rd, Chestertown, MD 21620

      Last Sold Summary

      • 31% Above List Price
      • $172/SF
      • 23 Days On Market
      • Last Sold Price $215,000
      • Aug 14, 2023

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /20

    $155,000

    Sold May 13, 2026

    132 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1949

    Last Sold Summary

    • 22% Below List Price
    • $170/SF
    • 74 Days On Market

    Current Estimated Value $169,423

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
    • /21

      Est $319,252

      Not Listed For Sale

      23240 Clarissa Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,404 Sq Ft
      • Built 1999
      23240 Clarissa Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $207/SF
      • 5 Days On Market
      • Last Sold Price $290,000
      • Nov 01, 2023

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

  • /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
    • /20

      Est $280,780

      Not Listed For Sale

      306 Roosevelt Dr, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,152 Sq Ft
      • Built 1966
      306 Roosevelt Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $217/SF
      • 2 Days On Market
      • Last Sold Price $250,000
      • Feb 29, 2024

      Last Listing Agent Theresa Stewart Patterson-Schwartz Real Estate

  • /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 $499,134

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
    • /23

      Est $325,302

      Not Listed For Sale

      27370 Morgnec Rd, Chestertown, MD 21620

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft
      • Built 1969
      27370 Morgnec Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $298/SF
      • 12 Days On Market
      • Last Sold Price $300,000
      • Apr 24, 2024

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • /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 $906,970

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
    • /47

      Est $587,620

      Not Listed For Sale

      223 S Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,004 Sq Ft
      • Built 2006
      223 S Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $267/SF
      • 166 Days On Market
      • Last Sold Price $535,000
      • Nov 30, 2023

      Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

  • /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 $909,077

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
    • /46

      Est $328,412

      Not Listed For Sale

      9769 Augustine Herman Hwy, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,456 Sq Ft
      • Built 1961
      9769 Augustine Herman Hwy, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $192/SF
      • 5 Days On Market
      • Last Sold Price $279,000
      • Sep 27, 2024

      Last Listing Agent Rosella Hunter RE/MAX

  • /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 $362,388

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

    127 Char Nor Manor Blvd, Chestertown, MD 21620
    • /37

      Est $303,750

      Not Listed For Sale

      202 Glen St, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,252 Sq Ft
      • Built 1966
      202 Glen St, Chestertown, MD 21620

      Last Sold Summary

      • 5% Above List Price
      • $232/SF
      • 104 Days On Market
      • Last Sold Price $290,000
      • May 08, 2025

      Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

  • /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 $588,312

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
    • /43

      Est $417,116

      Not Listed For Sale

      106 Devon Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 2001
      106 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $226/SF
      • 3 Days On Market
      • Last Sold Price $385,000
      • Feb 15, 2024

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /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 $348,344

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

    10751 Millbrook Dr, Chestertown, MD 21620
    • /51

      Est $1,094,563

      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

      • 27% Above List Price
      • $285/SF
      • 106 Days On Market
      • Last Sold Price $865,000
      • Aug 11, 2023

      Last Listing Agent William Norris Select Land & Homes, 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 $303,030

    Last Listing Agent Bronwyn Scott Samson Properties

    10670 Tintah Rd, Chestertown, MD 21620
    • /21

      Est $342,927

      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

      • 6% Above List Price
      • $137/SF
      • 18 Days On Market
      • Last Sold Price $325,000
      • Mar 06, 2025

      Last Listing Agent Jo Ann Edwards The Hogans Agency

  • /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 $314,538

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
    • /54

      Est $719,132

      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

      • 31% Above List Price
      • $194/SF
      • 5 Days On Market
      • Last Sold Price $550,000
      • Jun 20, 2023

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /63

    $695,000

    Sold May 18, 2026

    10087 John Carvill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1983

    Last Sold Summary

    • $444/SF
    • 8 Days On Market

    Current Estimated Value $655,379

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10087 John Carvill Rd, Chestertown, MD 21620
    • /24

      Est $318,380

      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

      • 16% Above List Price
      • $191/SF
      • 11 Days On Market
      • Last Sold Price $275,000
      • May 31, 2023

      Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

  • /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 $648,101

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
    • /59

      Est $1,559,243

      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
      • Dec 20, 2024

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /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 $696,734

    Last Listing Agent Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
    • /30

      Est $435,501

      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
      • Jun 28, 2024

      Last Listing Agent Carol Tinnin RE/MAX

  • /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 $247,958

    Last Listing Agent April Heim Rosendale Realty

    112 Metcalf Rd, Chestertown, MD 21620
    • /52

      Est $664,561

      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
      • Dec 11, 2023

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • /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 $410,834

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
    • /29

      Est $712,448

      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

      • 19% Above List Price
      • $225/SF
      • 155 Days On Market
      • Last Sold Price $600,000
      • Feb 06, 2025

      Last Listing Agent Paula Ruckelshaus Long & Foster

  • /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 $361,405

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
    • /63

      Est $645,524

      Not Listed For Sale

      209 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,328 Sq Ft
      • Built 1885
      209 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 21% Above List Price
      • $230/SF
      • 10 Days On Market
      • Last Sold Price $535,000
      • Mar 13, 2025

      Last Listing Agent Andrea Alderdice Long & Foster

  • /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
    • /53

      Est $440,662

      Not Listed For Sale

      25740 Collins Ave, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,389 Sq Ft
      • Built 1956
      25740 Collins Ave, Chestertown, MD 21620

      Last Sold Summary

      • 18% Above List Price
      • $111/SF
      • 29 Days On Market
      • Last Sold Price $375,000
      • Apr 16, 2025

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /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 $803,041

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, Chestertown, MD 21620
    • /24

      Est $322,034

      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

      • 20% Above List Price
      • $128/SF
      • 3 Days On Market
      • Last Sold Price $267,250
      • Jul 01, 2024

      Last Listing Agent Stacy Kendall Cross Street Realtors LLC

Showing Results 481 - 520, Page 13 of 18

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