6,817

Chestertown, MD Homes

Section Image
  • 25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    25800 Collins Ave, Chestertown, MD 21620
    /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 $469,191

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
    • 10175 John Carvill Rd, Chestertown, MD 21620
      10175 John Carvill Rd, Chestertown, MD 21620
      10175 John Carvill Rd, Chestertown, MD 21620
      /72

      Est $641,207

      Not Listed For Sale

      10175 John Carvill Rd, Chestertown, MD 21620

      • 5 Beds
      • 3.5 Baths
      • 3,155 Sq Ft
      • Built 1994
      10175 John Carvill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 11 Days On Market

      Last Listing Agent Hayley Norris Select Land & Homes, LLC

  • 23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    23065 Old Fairlee Rd, Chestertown, MD 21620
    /10

    $145,000

    Sold Oct 14, 2025

    23065 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1957

    Last Sold Summary

    • $123/SF
    • 5 Days On Market

    Current Estimated Value $159,425

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    23065 Old Fairlee Rd, Chestertown, MD 21620
    • 5772 Johnsontown Rd, Chestertown, MD 21620
      5772 Johnsontown Rd, Chestertown, MD 21620
      5772 Johnsontown Rd, Chestertown, MD 21620
      /20

      Est $268,452

      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

      Last Listing Agent Beth Green Doug Ashley Realtors, LLC

  • 100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    100 Prospect St, Chestertown, MD 21620
    /21

    $215,000

    Sold Jul 21, 2026

    100 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft
    • Built 1953

    Last Sold Summary

    • $157/SF
    • 5 Days On Market

    Current Estimated Value $212,252

    Last Listing Agent David Moore Real Broker, LLC

    100 Prospect St, Chestertown, MD 21620
    • 10755 Glenola Rd, Chestertown, MD 21620
      10755 Glenola Rd, Chestertown, MD 21620
      10755 Glenola Rd, Chestertown, MD 21620
      /17

      Est $276,680

      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

      Last Listing Agent Matthew Altizer ANR Realty, LLC

  • 1904 Pondtown Rd, Chestertown, MD 21620
    1904 Pondtown Rd, Chestertown, MD 21620
    1904 Pondtown Rd, Chestertown, MD 21620
    /11

    $247,500

    Sold Aug 10, 2026

    1904 Pondtown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,967 Sq Ft
    • Built 1972

    Last Sold Summary

    • 7% Below List Price
    • $126/SF
    • 51 Days On Market

    Current Estimated Value $268,375

    Last Listing Agent Lonnie Gilmore Keller Williams Flagship

    1904 Pondtown Rd, 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 $834,699

      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

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • 9816 Fairlee Rd, Chestertown, MD 21620
    9816 Fairlee Rd, Chestertown, MD 21620
    9816 Fairlee Rd, Chestertown, MD 21620
    /48

    $535,000

    Sold Jul 10, 2026

    9816 Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft
    • Built 1970

    Last Sold Summary

    • $329/SF
    • 13 Days On Market

    Current Estimated Value $527,177

    Last Listing Agent Scott Hogan Long & Foster Real Estate, Inc.

    9816 Fairlee Rd, Chestertown, MD 21620
    • 310 Hilltop Ln, Chestertown, MD 21620
      310 Hilltop Ln, Chestertown, MD 21620
      310 Hilltop Ln, Chestertown, MD 21620
      /18

      Est $214,067

      Not Listed For Sale

      310 Hilltop Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,216 Sq Ft
      • Built 2005
      310 Hilltop Ln, Chestertown, MD 21620

      Last Sold Summary

      • 24 Days On Market

      Last Listing Agent Clint Evans Cross Street Realtors LLC

  • 126 Metcalf Rd, Chestertown, MD 21620
    126 Metcalf Rd, Chestertown, MD 21620
    126 Metcalf Rd, Chestertown, MD 21620
    /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 $234,479

    Last Listing Agent Brenda Fornos Taylor Properties

    126 Metcalf Rd, 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 $293,023

      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

      Last Listing Agent Sarah King Cross Street Realtors LLC

  • 205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    205 River Rd, Chestertown, MD 21620
    /68

    $855,000

    Sold Jun 24, 2026

    205 River Rd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Below List Price
    • $297/SF
    • 6 Days On Market

    Current Estimated Value $744,029

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    205 River Rd, Chestertown, MD 21620
    • 10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      10572 Klamath Rd, Chestertown, MD 21620
      /27

      Est $294,563

      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

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    10165 John Carvill Rd, Chestertown, MD 21620
    /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 $576,047

    Last Listing Agent Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
    • 219 Philosophers Terrace, Chestertown, MD 21620
      219 Philosophers Terrace, Chestertown, MD 21620
      219 Philosophers Terrace, Chestertown, MD 21620
      /8

      Est $434,255

      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

      Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

  • 201 Radcliffe Dr, Chestertown, MD 21620
    201 Radcliffe Dr, Chestertown, MD 21620
    201 Radcliffe Dr, Chestertown, MD 21620
    /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 $792,172

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620
    • 8605 Camp Rd, Chestertown, MD 21620
      8605 Camp Rd, Chestertown, MD 21620
      8605 Camp Rd, Chestertown, MD 21620
      /51

      Est $378,861

      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

      Last Listing Agent Crystal Smith RE/MAX Executive

  • 109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    109 Metcalfe Rd, Chestertown, MD 21620
    /28

    $264,900

    Sold May 26, 2026

    109 Metcalfe Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2025

    Last Sold Summary

    • $207/SF
    • 124 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    109 Metcalfe Rd, Chestertown, MD 21620
    • 10724 Foreston Rd, Chestertown, MD 21620
      10724 Foreston Rd, Chestertown, MD 21620
      10724 Foreston Rd, Chestertown, MD 21620
      /35

      Est $370,674

      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

      Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

  • 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
    • 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

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

  • 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 $600,979

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley 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 $727,522

      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

      Last Listing Agent Lynn Hilfiker Gunther-McClary Real Estate

  • 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 $299,935

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    154 Longfellow Dr, 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 $579,625

      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

      Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

  • 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
    • 217 Birch Run Rd, Chestertown, MD 21620
      217 Birch Run Rd, Chestertown, MD 21620
      217 Birch Run Rd, Chestertown, MD 21620
      /50

      Est $529,020

      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

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • 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
    • 7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      7509 Sunburst Ave, Chestertown, MD 21620
      /15

      Est $232,279

      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

      Last Listing Agent Tiffany Dodson Samson Properties

  • 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
    • 811 S Meadowview Dr, Chestertown, MD 21620
      811 S Meadowview Dr, Chestertown, MD 21620
      811 S Meadowview Dr, Chestertown, MD 21620
      /45

      Est $479,720

      Not Listed For Sale

      811 S Meadowview Dr, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,064 Sq Ft
      • Built 2002
      811 S Meadowview Dr, Chestertown, MD 21620

      Last Sold Summary

      • 4 Days On Market

      Last Listing Agent Christine Leonard Redfin Corp

  • 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 $512,724

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

    110 S Queen St, Chestertown, MD 21620
    • 100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      100 Malone Ave, Chestertown, MD 21620
      /39

      Est $346,034

      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

      • 94 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • 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
    • 100 Acorn Dr, Chestertown, MD 21620
      100 Acorn Dr, Chestertown, MD 21620
      100 Acorn Dr, Chestertown, MD 21620
      /27

      Est $296,322

      Not Listed For Sale

      100 Acorn Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,930 Sq Ft
      • Built 2004
      100 Acorn Dr, Chestertown, MD 21620

      Last Sold Summary

      • 164 Days On Market

      Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  • 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 $208,310

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    113 Pear Tree Point Rd, Chestertown, MD 21620
    • 204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      204 Richard Dr, Chestertown, MD 21620
      /54

      Est $403,966

      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

      • 7 Days On Market

      Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

  • 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 $361,801

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    217 Philosophers Terrace, Chestertown, MD 21620
    • 898 Washington Ave, Chestertown, MD 21620
      898 Washington Ave, Chestertown, MD 21620
      898 Washington Ave, Chestertown, MD 21620
      /34

      Est $261,902

      Not Listed For Sale

      898 Washington Ave, Chestertown, MD 21620

      • 2 Beds
      • 2 Baths
      • 1,384 Sq Ft
      • Built 1967
      898 Washington Ave, Chestertown, MD 21620

      Last Sold Summary

      • 5 Days On Market

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

Showing Results 441 - 480, Page 12 of 18

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