6,886

Chestertown, MD Homes

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  • /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 $276,987

    Last Listing Agent Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
    • /41

      Est $482,637 Not Listed For Sale

      100 Foxview Ct, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,000 Sq Ft
      • Built 1999
      100 Foxview Ct, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $145/SF
      • 7 Days On Market

      Last Sold Price $435,000

      Last Listing Agent Sarah Ulrick Rock Hall Properties

  • /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 $187,586

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
    • /56

      Est $492,685 Not Listed For Sale

      306 Mayfair Dr, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,784 Sq Ft
      • Built 1995
      306 Mayfair Dr, Chestertown, MD 21620

      Last Sold Summary

      • 17% Above List Price
      • $151/SF
      • 2 Days On Market

      Last Sold Price $419,900

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /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 $592,045

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
    • /73

      Est $272,159 Not Listed For Sale

      22954 Bay Shore Rd, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 2,336 Sq Ft
      • Built 1881
      22954 Bay Shore Rd, Chestertown, MD 21620

      Last Sold Summary

      • 43% Above List Price
      • $81/SF
      • 294 Days On Market

      Last Sold Price $190,000

      Last Listing Agent Colleen Minahan Long & Foster

  • /16

    $195,000 Sold Apr 11, 2025

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1955

    Last Sold Summary

    • $144/SF
    • 0 Days On Market

    Current Estimated Value $203,826

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    • /32

      Est $282,072 Not Listed For Sale

      8891 Georgetown Rd, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 1,600 Sq Ft
      • Built 1900
      8891 Georgetown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 33% Above List Price
      • $133/SF
      • 8 Days On Market

      Last Sold Price $212,619

      Last Listing Agent Carlos Contreras Caprika Realty

  • /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
    • /17

      Est $316,634 Not Listed For Sale

      104 Oak Leaf Dr, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 1,840 Sq Ft
      • Built 2003
      104 Oak Leaf Dr, Chestertown, MD 21620

      Last Sold Summary

      • 12% Above List Price
      • $154/SF
      • 38 Days On Market

      Last Sold Price $283,000

      Last Listing Agent Krystal Zellner Crown Homes Real Estate

  • /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
    • /24

      Est $317,686 Not Listed For Sale

      307 Cedar St, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,472 Sq Ft
      • Built 1962
      307 Cedar St, Chestertown, MD 21620

      Last Sold Summary

      • 25% Above List Price
      • $173/SF
      • 1 Day On Market

      Last Sold Price $255,000

      Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

  • /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
    • /54

      Est $479,483 Not Listed For Sale

      109 Birch Run Rd, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,428 Sq Ft
      • Built 1978
      109 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $315/SF

      Last Sold Price $450,000

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /44

    $560,000 Sold Apr 21, 2025

    7938 Radcliffe Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,408 Sq Ft
    • Built 1976

    Last Sold Summary

    • $233/SF
    • 115 Days On Market

    Current Estimated Value $592,776

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7938 Radcliffe Rd, Chestertown, MD 21620
    • /32

      Est $377,034 Not Listed For Sale

      23530 Clarissa Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,812 Sq Ft
      • Built 1993
      23530 Clarissa Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $190/SF
      • 3 Days On Market

      Last Sold Price $345,000

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • /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
    • /5

      Not Listed For Sale

      24581 Willow Oak Ln, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,352 Sq Ft
      • Built 2007
      24581 Willow Oak Ln, Chestertown, MD 21620

      Last Sold Summary

      • $107/SF
      • 4 Days On Market

      Last Sold Price $145,000

      Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  • /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 $309,757

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    116 Oak Leaf Dr, Chestertown, MD 21620
    • /45

      Est $567,009 Not Listed For Sale

      27325 Preston Ln, Chestertown, MD 21620

      • 3 Beds
      • 3 Baths
      • 2,824 Sq Ft
      • Built 2000
      27325 Preston Ln, Chestertown, MD 21620

      Last Sold Summary

      • 24% Above List Price
      • $161/SF
      • 1 Day On Market

      Last Sold Price $456,000

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

  • /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 $274,723

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 21620
    • /25

      Est $329,088 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

      • 10% Above List Price
      • $205/SF
      • 10 Days On Market

      Last Sold Price $299,900

      Last Listing Agent Jody Baker Cross Street Realtors LLC

  • /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 $365,026

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

    517 High St, Chestertown, MD 21620
    • /17

      Est $283,732 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

      • 32% Above List Price
      • $172/SF
      • 23 Days On Market

      Last Sold Price $215,000

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /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 $724,333

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
    • /38

      Est $633,553 Not Listed For Sale

      225 Richard Dr, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,749 Sq Ft
      • Built 1977
      225 Richard Dr, Chestertown, MD 21620

      Last Sold Summary

      • 23% Above List Price
      • $188/SF
      • 7 Days On Market

      Last Sold Price $517,000

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /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
    • /21

      Est $321,311 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

      • 11% Above List Price
      • $207/SF
      • 5 Days On Market

      Last Sold Price $290,000

      Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

  • /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 $394,464

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
    • /20

      Est $274,150 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

      • 10% Above List Price
      • $217/SF
      • 2 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Theresa Stewart Patterson-Schwartz Real Estate

  • /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 $1,098,681

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
    • /23

      Est $316,162 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

      • 5% Above List Price
      • $298/SF
      • 12 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Andrew Meikle Doug Ashley 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 $189,715

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
    • /47

      Est $588,470 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

      Last Listing Agent Grace Crockett Doug Ashley Realtors, 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 $422,829

    Last Listing Agent Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
    • /18

      Est $392,602 Not Listed For Sale

      1005 Twin Ct, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,854 Sq Ft
      • Built 2002
      1005 Twin Ct, Chestertown, MD 21620

      Last Sold Summary

      • 6% Above List Price
      • $200/SF
      • 144 Days On Market

      Last Sold Price $370,000

      Last Listing Agent Scott Saunders Coldwell Banker Waterman Realty

  • /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 $506,474

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
    • /46

      Est $316,863 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

      • 14% Above List Price
      • $192/SF
      • 5 Days On Market

      Last Sold Price $279,000

      Last Listing Agent Rosella Hunter RE/MAX

  • /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 $894,933

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
    • /43

      Est $447,705 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

      • 16% Above List Price
      • $226/SF
      • 3 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

Showing Results 441 - 480, Page 12 of 18

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