6,890

Chestertown, MD Homes

Section Image
  • 304 Hadaway Dr, Chestertown, MD 21620
    304 Hadaway Dr, Chestertown, MD 21620
    /2

    $300,000

    Sold Jul 30, 2026

    304 Hadaway Dr, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1960

    Last Sold Summary

    • 9% Below List Price
    • $226/SF
    • 48 Days On Market

    Current Estimated Value $310,066

    Last Listing Agent Dawn Kane Redfin Corporation

    304 Hadaway Dr, Chestertown, MD 21620
    • 213 Devon Dr, Chestertown, MD 21620
      213 Devon Dr, Chestertown, MD 21620
      213 Devon Dr, Chestertown, MD 21620
      /24

      Est $405,335

      Not Listed For Sale

      213 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,472 Sq Ft
      • Built 2005
      213 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 85 Days On Market

  • 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 $272,338

    Last Listing Agent Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
    • 614 High St, Chestertown, MD 21620
      614 High St, Chestertown, MD 21620
      614 High St, Chestertown, MD 21620
      /22

      Est $207,255

      Not Listed For Sale

      614 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1920
      614 High St, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 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 $594,782

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, Chestertown, MD 21620
    • 612 High St, Chestertown, MD 21620
      612 High St, Chestertown, MD 21620
      612 High St, Chestertown, MD 21620
      /21

      Est $200,405

      Not Listed For Sale

      612 High St, Chestertown, MD 21620

      • 2 Beds
      • 1.5 Baths
      • 1,064 Sq Ft
      • Built 1920
      612 High St, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 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
    • 7996 Aldan Dr, Chestertown, MD 21620
      7996 Aldan Dr, Chestertown, MD 21620
      7996 Aldan Dr, Chestertown, MD 21620
      /72

      Est $869,376

      Not Listed For Sale

      7996 Aldan Dr, Chestertown, MD 21620

      • 4 Beds
      • 3.5 Baths
      • 3,743 Sq Ft
      • Built 2001
      7996 Aldan Dr, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • 154 Longfellow Dr, Chestertown, MD 21620
    154 Longfellow Dr, Chestertown, MD 21620
    /2

    $300,000

    Sold May 27, 2026

    154 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $213/SF
    • 32 Days On Market

    Current Estimated Value $299,190

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    154 Longfellow Dr, Chestertown, MD 21620
    • 7988 Aldan Dr, Chestertown, MD 21620
      7988 Aldan Dr, Chestertown, MD 21620
      7988 Aldan Dr, Chestertown, MD 21620
      /56

      Est $788,217

      Not Listed For Sale

      7988 Aldan Dr, Chestertown, MD 21620

      • 5 Beds
      • 3 Baths
      • 3,394 Sq Ft
      • Built 2000
      7988 Aldan Dr, Chestertown, MD 21620

      Last Sold Summary

      • 2 Days On Market

  • 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 $1,559,248

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
    • 5772 Johnsontown Rd, Chestertown, MD 21620
      5772 Johnsontown Rd, Chestertown, MD 21620
      5772 Johnsontown Rd, Chestertown, MD 21620
      /20

      Est $283,933

      Not Listed For Sale

      5772 Johnsontown Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,344 Sq Ft
      • Built 2002
      5772 Johnsontown Rd, Chestertown, MD 21620

      Last Sold Summary

      • 3 Days On Market

  • 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 $4,186,004

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
    • 10755 Glenola Rd, Chestertown, MD 21620
      10755 Glenola Rd, Chestertown, MD 21620
      10755 Glenola Rd, Chestertown, MD 21620
      /17

      Est $281,203

      Not Listed For Sale

      10755 Glenola Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,237 Sq Ft
      • Built 1997
      10755 Glenola Rd, Chestertown, MD 21620

      Last Sold Summary

      • 88 Days On Market

  • 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
    • 8550 Caulks Field Rd, Chestertown, MD 21620
      8550 Caulks Field Rd, Chestertown, MD 21620
      8550 Caulks Field Rd, Chestertown, MD 21620
      /25

      Est $340,859

      Not Listed For Sale

      8550 Caulks Field Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,568 Sq Ft
      • Built 2006
      8550 Caulks Field Rd, Chestertown, MD 21620

      Last Sold Summary

      • 7 Days On Market

  • 110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    110 S Queen St, Chestertown, MD 21620
    /30

    $541,500

    Sold Jul 10, 2026

    110 S Queen St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,785 Sq Ft
    • Built 1914

    Last Sold Summary

    • 3% Above List Price
    • $303/SF
    • 17 Days On Market

    Current Estimated Value $607,959

    Last Listing Agent J.P. Graham Cross Street Realtors LLC

    110 S Queen St, Chestertown, MD 21620
    • 8049 Quaker Neck Rd, Chestertown, MD 21620
      8049 Quaker Neck Rd, Chestertown, MD 21620
      8049 Quaker Neck Rd, Chestertown, MD 21620
      /28

      Est $822,632

      Not Listed For Sale

      8049 Quaker Neck Rd, Chestertown, MD 21620

      • 4 Beds
      • 2 Baths
      • 1,660 Sq Ft
      • Built 1945
      8049 Quaker Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 98 Days On Market

  • 21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    21217 Texas Ave, Chestertown, MD 21620
    /20

    $244,000

    Sold Jul 27, 2026

    21217 Texas Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1952

    Last Sold Summary

    • 8% Below List Price
    • $268/SF
    • 83 Days On Market

    Current Estimated Value $242,218

    Last Listing Agent Terry Catalano RE/MAX Leading Edge

    21217 Texas Ave, Chestertown, MD 21620
    • 403 E Campus Ave, Chestertown, MD 21620
      403 E Campus Ave, Chestertown, MD 21620
      403 E Campus Ave, Chestertown, MD 21620
      /28

      Est $303,248

      Not Listed For Sale

      403 E Campus Ave, Chestertown, MD 21620

      • 3 Beds
      • 1 Bath
      • 1,248 Sq Ft
      • Built 1947
      403 E Campus Ave, Chestertown, MD 21620

      Last Sold Summary

      • 62 Days On Market

  • 113 Pear Tree Point Rd, Chestertown, MD 21620
    113 Pear Tree Point Rd, Chestertown, MD 21620
    /2

    $175,000

    Sold Jun 05, 2026

    113 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • Built 1973

    Last Sold Summary

    • 30% Below List Price
    • $135/SF
    • 47 Days On Market

    Current Estimated Value $252,020

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    113 Pear Tree Point Rd, Chestertown, MD 21620
    • 10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      /27

      Est $306,424

      Not Listed For Sale

      10572 Klamath Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft
      • Built 1996
      10572 Klamath Rd, Chestertown, MD 21620

      Last Sold Summary

      • 70 Days On Market

  • 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 $359,287

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    217 Philosophers Terrace, Chestertown, MD 21620
    • 219 Philosophers Terrace, Chestertown, MD 21620
      219 Philosophers Terrace, Chestertown, MD 21620
      219 Philosophers Terrace, Chestertown, MD 21620
      /8

      Est $431,107

      Not Listed For Sale

      219 Philosophers Terrace, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,872 Sq Ft
      • Built 1932
      219 Philosophers Terrace, Chestertown, MD 21620

      Last Sold Summary

      • 0 Days On Market

  • 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 $269,726

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 21620
    • 8605 Camp Rd, Chestertown, MD 21620
      8605 Camp Rd, Chestertown, MD 21620
      8605 Camp Rd, Chestertown, MD 21620
      /51

      Est $374,739

      Not Listed For Sale

      8605 Camp Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft
      • Built 1968
      8605 Camp Rd, Chestertown, MD 21620

      Last Sold Summary

      • 10 Days On Market

  • 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 $375,604

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

    517 High St, Chestertown, MD 21620
    • 10724 Foreston Rd, Chestertown, MD 21620
      10724 Foreston Rd, Chestertown, MD 21620
      10724 Foreston Rd, Chestertown, MD 21620
      /35

      Est $369,856

      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

      • 3 Days On Market

  • 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 $496,405

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    515 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

      Est $375,864

      Not Listed For Sale

      10705 Millbrook Dr, Chestertown, MD 21620

      • 4 Beds
      • 3 Baths
      • 2,106 Sq Ft
      • Built 1988
      10705 Millbrook Dr, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

  • 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 $712,672

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
    • 112 S Mill St, Chestertown, MD 21620
      112 S Mill St, Chestertown, MD 21620
      112 S Mill St, Chestertown, MD 21620
      /34

      Est $767,581

      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

      • 49 Days On Market

  • 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
    • 209 Birch Run Rd, Chestertown, MD 21620
      209 Birch Run Rd, Chestertown, MD 21620
      209 Birch Run Rd, Chestertown, MD 21620
      /25

      Est $578,953

      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

      • 3 Days On Market

  • 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 $398,706

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
    • 203 Leeds Ct, Chestertown, MD 21620
      203 Leeds Ct, Chestertown, MD 21620
      203 Leeds Ct, Chestertown, MD 21620
      /41

      Est $475,378

      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

      • 5 Days On Market

  • 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 $1,144,916

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
    • 217 Birch Run Rd, Chestertown, MD 21620
      217 Birch Run Rd, Chestertown, MD 21620
      217 Birch Run Rd, Chestertown, MD 21620
      /50

      Est $526,220

      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

      • 35 Days On Market

  • 221 Dutchess Rd, Chestertown, MD 21620
    221 Dutchess Rd, Chestertown, MD 21620
    /2

    $228,000

    Sold Jul 13, 2026

    221 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,260 Sq Ft
    • Built 1974

    Last Sold Summary

    • $101/SF
    • 0 Days On Market

    Current Estimated Value $304,898

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    221 Dutchess Rd, Chestertown, MD 21620
    • 7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      /15

      Est $241,721

      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

      • 6 Days On Market

Showing Results 441 - 480, Page 12 of 18

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