6,896

Chestertown, MD Homes

Section Image
  • /31

    $435,000

    Sold Nov 03, 2025

    25800 Collins Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft
    • Built 1960

    Last Sold Summary

    • $201/SF
    • 22 Days On Market

    Current Estimated Value $478,212

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
    • /35

      Est $394,656

      Not Listed For Sale

      10724 Foreston Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1995
      10724 Foreston Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11% Above List Price
      • $190/SF
      • 3 Days On Market
      • Last Sold Price $355,675
      • Feb 28, 2025

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • /25

    $230,000

    Sold Nov 20, 2025

    126 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $202/SF
    • 21 Days On Market

    Current Estimated Value $235,805

    Last Listing Agent Brenda Fornos Taylor Properties

    126 Metcalf Rd, Chestertown, MD 21620
    • /34

      Est $735,307

      Not Listed For Sale

      112 S Mill St, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,683 Sq Ft
      • Built 1840
      112 S Mill St, Chestertown, MD 21620

      Last Sold Summary

      • 3% Above List Price
      • $266/SF
      • 49 Days On Market
      • Last Sold Price $713,000
      • Nov 07, 2023

      Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

  • /20

    $525,000

    Sold Oct 17, 2025

    10165 John Carvill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,774 Sq Ft
    • Built 1987

    Last Sold Summary

    • $189/SF
    • 28 Days On Market

    Current Estimated Value $581,949

    Last Listing Agent Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
    • /25

      Est $638,242

      Not Listed For Sale

      209 Birch Run Rd, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,488 Sq Ft
      • Built 1980
      209 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 13% Above List Price
      • $227/SF
      • 3 Days On Market
      • Last Sold Price $565,000
      • Nov 18, 2024

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • /19

    $335,000

    Sold Aug 08, 2025

    10578 Tonopah Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $223/SF
    • 17 Days On Market

    Current Estimated Value $337,102

    Last Listing Agent David Moore Real Broker, LLC

    10578 Tonopah Rd, Chestertown, MD 21620
    • /41

      Est $502,912

      Not Listed For Sale

      203 Leeds Ct, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,422 Sq Ft
      • Built 2005
      203 Leeds Ct, Chestertown, MD 21620

      Last Sold Summary

      • 27% Above List Price
      • $164/SF
      • 5 Days On Market
      • Last Sold Price $397,000
      • Jul 27, 2023

      Last Listing Agent Andrew Pallante Compass

  • /36

    $795,000

    Sold Nov 07, 2025

    201 Radcliffe Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,736 Sq Ft
    • Built 2011

    Last Sold Summary

    • $291/SF
    • 4 Days On Market

    Current Estimated Value $792,806

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620
    • /50

      Est $578,424

      Not Listed For Sale

      217 Birch Run Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,208 Sq Ft
      • Built 1984
      217 Birch Run Rd, Chestertown, MD 21620

      Last Sold Summary

      • 15% Above List Price
      • $227/SF
      • 35 Days On Market
      • Last Sold Price $501,000
      • Nov 14, 2024

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /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 $351,713

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
    • /15

      Est $252,213

      Not Listed For Sale

      7509 Sunburst Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,026 Sq Ft
      • Built 1989
      7509 Sunburst Ave, Chestertown, MD 21620

      Last Sold Summary

      • 10% Above List Price
      • $224/SF
      • 6 Days On Market
      • Last Sold Price $230,000
      • Apr 10, 2024

      Last Listing Agent Tiffany Dodson Samson Properties

  • /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 $280,007

    Last Listing Agent Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
    • /39

      Est $361,671

      Not Listed For Sale

      100 Malone Ave, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 2,444 Sq Ft
      • Built 1967
      100 Malone Ave, Chestertown, MD 21620

      Last Sold Summary

      • 26% Above List Price
      • $118/SF
      • 94 Days On Market
      • Last Sold Price $287,500
      • Dec 06, 2023

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /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 $202,983

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
    • /54

      Est $409,514

      Not Listed For Sale

      204 Richard Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,540 Sq Ft
      • Built 1972
      204 Richard Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2% Below List Price
      • $273/SF
      • 7 Days On Market
      • Last Sold Price $420,000
      • Nov 17, 2023

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • /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 $610,514

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
    • /62

      Est $730,392

      Not Listed For Sale

      115 N Queen St, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 2,496 Sq Ft
      • Built 1900
      115 N Queen St, Chestertown, MD 21620

      Last Sold Summary

      • 4% Below List Price
      • $304/SF
      • 4 Days On Market
      • Last Sold Price $760,000
      • Jun 30, 2023

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • /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
    • /56

      Est $881,653

      Not Listed For Sale

      307 Washington Ave, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,355 Sq Ft
      • Built 1936
      307 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 2% Above List Price
      • $258/SF
      • 130 Days On Market
      • Last Sold Price $866,395
      • Nov 14, 2024

      Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

  • /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 $1,511,440

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
    • /24

      Est $381,898

      Not Listed For Sale

      24291 Chestertown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1962
      24291 Chestertown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 8% Above List Price
      • $231/SF
      • 64 Days On Market
      • Last Sold Price $355,000
      • Dec 02, 2024

      Last Listing Agent Joelle Dolch Cross Street Realtors 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 $4,231,262

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
    • /18

      Est $739,125

      Not Listed For Sale

      425 High St, Chestertown, MD 21620

      • Studio
      • 3,114 Sq Ft
      • Built 1920
      425 High St, Chestertown, MD 21620

      Last Sold Summary

      • 32% Above List Price
      • $180/SF
      • 10 Days On Market
      • Last Sold Price $560,000
      • Sep 08, 2023

      Last Listing Agent William Norris Select Land & Homes, 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
    • /41

      Est $503,730

      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

      • 16% Above List Price
      • $145/SF
      • 7 Days On Market
      • Last Sold Price $435,000
      • Oct 24, 2024

      Last Listing Agent Sarah Ulrick Rock Hall Properties

  • /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
    • /56

      Est $531,735

      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

      • 27% Above List Price
      • $151/SF
      • 2 Days On Market
      • Last Sold Price $419,900
      • Dec 11, 2023

      Last Listing Agent Peter Heller 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 $279,085

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 21620
    • /38

      Est $308,897

      Not Listed For Sale

      116 Oak Leaf Dr, Chestertown, MD 21620

      • 2 Beds
      • 4 Baths
      • 1,867 Sq Ft
      • Built 2004
      116 Oak Leaf Dr, Chestertown, MD 21620

      Last Sold Summary

      • 7% Above List Price
      • $155/SF
      • 13 Days On Market
      • Last Sold Price $289,500
      • May 05, 2025

      Last Listing Agent Grace Crockett Doug Ashley 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 $371,495

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

    517 High St, Chestertown, MD 21620
    • /17

      Est $320,238

      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

      • 13% Above List Price
      • $154/SF
      • 38 Days On Market
      • Last Sold Price $283,000
      • Feb 19, 2025

      Last Listing Agent Krystal Zellner Crown Homes Real Estate

  • /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
    • /24

      Est $331,073

      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

      • 30% Above List Price
      • $173/SF
      • 1 Day On Market
      • Last Sold Price $255,000
      • Sep 13, 2023

      Last Listing Agent Kaitlyn Collins Benson & Mangold, 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 $736,793

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
    • /54

      Est $479,262

      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
      • Sep 16, 2024

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • /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
    • /32

      Est $373,519

      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

      • 8% Above List Price
      • $190/SF
      • 3 Days On Market
      • Last Sold Price $345,000
      • Jun 25, 2024

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, 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 $407,662

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
    • /45

      Est $582,528

      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

      • 28% Above List Price
      • $161/SF
      • 1 Day On Market
      • Last Sold Price $456,000
      • Sep 05, 2023

      Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

Showing Results 441 - 480, Page 12 of 18

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