6,896

Chestertown, MD Homes

Section Image
  • /43

    $262,500

    Sold May 29, 2025

    10705 Millbrook Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft
    • Built 1988

    Last Sold Summary

    • $125/SF
    • 87 Days On Market

    Current Estimated Value $382,758

    Last Listing Agent Edward Kowalski EXP Realty, LLC

    10705 Millbrook Dr, Chestertown, MD 21620
    • /22

      Est $496,866

      Not Listed For Sale

      7920 Carriage Ln, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 1,764 Sq Ft
      • Built 1976
      7920 Carriage Ln, Chestertown, MD 21620

      Last Sold Summary

      • 9% Above List Price
      • $257/SF
      • 21 Days On Market
      • Last Sold Price $454,000
      • Nov 17, 2023

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • /2

    $1,125,000

    Sold Jun 10, 2025

    101 Rivershore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,968 Sq Ft
    • Built 1950

    Last Sold Summary

    • $572/SF

    Current Estimated Value $985,539

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 Rivershore Rd, Chestertown, MD 21620
    • /34

      Est $499,602

      Not Listed For Sale

      209 E Campus Ave, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,397 Sq Ft
      • Built 1947
      209 E Campus Ave, Chestertown, MD 21620

      Last Sold Summary

      • 28% Above List Price
      • $163/SF
      • 145 Days On Market
      • Last Sold Price $390,000
      • Mar 01, 2024

      Last Listing Agent Sarah King Cross Street Realtors LLC

  • /3

    $13,000

    Sold Mar 24, 2026

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    • Land
    • 3,920 Sq Ft
    • $144,444 per Acre

    Last Sold Summary

    • 699 Days On Market

    Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
    • /64

      Est $1,495,560

      Not Listed For Sale

      9545 Chantilly Farm Ln, Chestertown, MD 21620

      • 3 Beds
      • 3.5 Baths
      • 2,200 Sq Ft
      • Built 1986
      9545 Chantilly Farm Ln, Chestertown, MD 21620

      Last Sold Summary

      • 13% Below List Price
      • $784/SF
      • 1 Day On Market
      • Last Sold Price $1,725,000
      • May 15, 2024

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /37

    $278,500

    Sold May 14, 2026

    107 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • Built 1974

    Last Sold Summary

    • 6% Below List Price
    • 11 Days On Market

    Current Estimated Value $296,318

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    107 Longfellow Dr, Chestertown, MD 21620
    • /44

      Est $652,610

      Not Listed For Sale

      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      • 3 Beds
      • 2 Baths
      • 2,240 Sq Ft
      • Built 1890
      5564 Quaker Neck Landing Rd, Chestertown, MD 21620

      Last Sold Summary

      • 19% Above List Price
      • $245/SF
      • 26 Days On Market
      • Last Sold Price $549,000
      • Jan 24, 2024

      Last Listing Agent Christopher McClary Gunther-McClary Real Estate

  • /18

    $375,000

    Sold Oct 10, 2025

    200 Fey Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1996

    Last Sold Summary

    • $239/SF
    • 19 Days On Market

    Current Estimated Value $385,058

    Last Listing Agent Erik Hoferer Long & Foster Real Estate, Inc.

    200 Fey Rd, Chestertown, MD 21620
    • /25

      Est $528,836

      Not Listed For Sale

      8500 Broad Neck Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,240 Sq Ft
      • Built 2014
      8500 Broad Neck Rd, Chestertown, MD 21620

      Last Sold Summary

      • 23% Above List Price
      • $192/SF
      • 42 Days On Market
      • Last Sold Price $430,000
      • Sep 11, 2024

      Last Listing Agent Ginny Dauses Coldwell Banker Waterman Realty

  • /23

    $296,337

    Sold Sep 30, 2025

    205 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft
    • Built 1955

    Last Sold Summary

    • $134/SF
    • 32 Days On Market

    Current Estimated Value $319,576

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, Chestertown, MD 21620
    • /44

      Est $435,738

      Not Listed For Sale

      208 Byford Dr, Chestertown, MD 21620

      • 3 Beds
      • 2.5 Baths
      • 2,045 Sq Ft
      • Built 1976
      208 Byford Dr, Chestertown, MD 21620

      Last Sold Summary

      • 19% Above List Price
      • $178/SF
      • 16 Days On Market
      • Last Sold Price $365,000
      • Jul 01, 2024

      Last Listing Agent Mary Fielding Coldwell Banker Chesapeake Real Estate Company

  • /35

    $510,184

    Sold May 29, 2025

    716 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $241/SF
    • 0 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    716 Aldora Dr, Chestertown, MD 21620
    • /24

      Est $540,787

      Not Listed For Sale

      247 Devon Dr, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 4,316 Sq Ft
      • Built 2006
      247 Devon Dr, Chestertown, MD 21620

      Last Sold Summary

      • 34% Above List Price
      • $94/SF
      • 36 Days On Market
      • Last Sold Price $405,000
      • Aug 23, 2023

      Last Listing Agent John Carroll Village Real Estate Company LLC

  • /49

    $960,000

    Sold Aug 27, 2025

    10715 Kasota Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,401 Sq Ft
    • Built 2005

    Last Sold Summary

    • $282/SF
    • 5 Days On Market

    Current Estimated Value $1,012,749

    Last Listing Agent Sarah King Cross Street Realtors LLC

    10715 Kasota Rd, Chestertown, MD 21620
    • /24

      Est $427,022

      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

      • 22% Above List Price
      • $142/SF
      • 85 Days On Market
      • Last Sold Price $350,000
      • Sep 27, 2024

      Last Listing Agent Christopher Buss Weichert Corporate

  • /8

    $360,000

    Sold Jun 27, 2025

    200 Hoffman Ln, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1957

    Last Sold Summary

    • $319/SF
    • 15 Days On Market

    Current Estimated Value $423,556

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    200 Hoffman Ln, Chestertown, MD 21620
    • /22

      Est $225,388

      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

      • 7% Above List Price
      • $197/SF
      • 3 Days On Market
      • Last Sold Price $210,000
      • Apr 19, 2024

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • /32

    $645,000

    Sold Jul 31, 2025

    7682 Waterview Ln, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,240 Sq Ft
    • Built 1989

    Last Sold Summary

    • $288/SF
    • 2 Days On Market

    Current Estimated Value $664,528

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7682 Waterview Ln, Chestertown, MD 21620
    • /21

      Est $219,204

      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

      • 12% Above List Price
      • $183/SF
      • 3 Days On Market
      • Last Sold Price $195,000
      • Apr 19, 2024

      Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

  • /10

    $65,000

    Sold Aug 11, 2025

    9020 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 2.36 Acres
    • $27,542 per Acre

    Last Sold Summary

    • 54 Days On Market

    Current Estimated Value $65,609

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    9020 Georgetown Rd, Chestertown, MD 21620
    • /72

      Est $894,895

      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

      • 20% Above List Price
      • $199/SF
      • 10 Days On Market
      • Last Sold Price $745,000
      • Dec 29, 2023

      Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

  • /5

    $15,000

    Sold May 15, 2026

    23698 L Rd, Chestertown, MD 21620

    • Land
    • 2.6 Acres
    • $5,769 per Acre

    Last Sold Summary

    • 48% Below List Price
    • 127 Days On Market

    Current Estimated Value $102,242

    Last Listing Agent Joe Howerton Taylor Properties

    23698 L Rd, Chestertown, MD 21620
    • /12

      Est $794,782

      Not Listed For Sale

      8042 Brices Mill Rd, Chestertown, MD 21620

      • 4 Beds
      • 2.5 Baths
      • 2,430 Sq Ft
      • Built 1990
      8042 Brices Mill Rd, Chestertown, MD 21620

      Last Sold Summary

      • 9% Below List Price
      • $358/SF
      • 23 Days On Market
      • Last Sold Price $870,000
      • May 24, 2023

      Last Listing Agent William Norris Select Land & Homes, LLC

  • /37

    $525,000

    Sold Jun 30, 2025

    201 Pondview Ct, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,016 Sq Ft
    • Built 2001

    Last Sold Summary

    • $174/SF
    • 2 Days On Market

    Current Estimated Value $571,832

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    201 Pondview Ct, Chestertown, MD 21620
    • /20

      Est $339,372

      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

      • $253/SF
      • 3 Days On Market
      • Last Sold Price $340,000
      • May 03, 2024

      Last Listing Agent Beth Green Doug Ashley Realtors, LLC

  • /40

    $750,000

    Sold May 22, 2025

    5594 Langford Bay Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft
    • Built 1956

    Last Sold Summary

    • $446/SF
    • 0 Days On Market

    Current Estimated Value $821,984

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, Chestertown, MD 21620
    • /17

      Est $298,055

      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

      • 30% Above List Price
      • $186/SF
      • 88 Days On Market
      • Last Sold Price $229,900
      • Jan 04, 2024

      Last Listing Agent Matthew Altizer ANR Realty, LLC

  • /46

    $425,000

    Sold Nov 17, 2025

    201 Boundary Ave, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1968

    Last Sold Summary

    • $137/SF
    • 59 Days On Market

    Current Estimated Value $441,978

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
    • /25

      Est $371,938

      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

      • 18% Above List Price
      • $201/SF
      • 7 Days On Market
      • Last Sold Price $315,000
      • Aug 16, 2023

      Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

  • /32

    $360,000

    Sold Jun 12, 2025

    216 Silver Heel Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2022

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $368,718

    Last Listing Agent Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620
    • /28

      Est $911,931

      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

      • 8% Above List Price
      • $511/SF
      • 98 Days On Market
      • Last Sold Price $848,000
      • Aug 28, 2024

      Last Listing Agent John Burke Gunther-McClary Real Estate

  • /21

    $255,000

    Sold Jan 16, 2026

    318 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1966

    Last Sold Summary

    • $266/SF
    • 58 Days On Market

    Current Estimated Value $255,650

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, Chestertown, MD 21620
    • /28

      Est $290,858

      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

      • 6% Above List Price
      • $220/SF
      • 62 Days On Market
      • Last Sold Price $275,000
      • Feb 09, 2024

      Last Listing Agent Sarah King Cross Street Realtors LLC

  • /73

    $850,000

    Sold Dec 19, 2025

    492 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 3,720 Sq Ft
    • Built 2001

    Last Sold Summary

    • $228/SF
    • 27 Days On Market

    Current Estimated Value $888,362

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
    • /27

      Est $317,188

      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

      • 18% Above List Price
      • $219/SF
      • 70 Days On Market
      • Last Sold Price $269,900
      • Sep 20, 2024

      Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

  • /26

    $235,000

    Sold Aug 07, 2025

    118 Tuxedo Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 121 Days On Market

    Current Estimated Value $253,306

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo Rd, Chestertown, MD 21620
    • /8

      Est $461,833

      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

      • 15% Above List Price
      • $214/SF
      • 0 Days On Market
      • Last Sold Price $400,000
      • Sep 25, 2023

      Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

  • /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
    • /51

      Est $384,554

      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

      • 4% Above List Price
      • $285/SF
      • 10 Days On Market
      • Last Sold Price $370,000
      • May 08, 2025

      Last Listing Agent Crystal Smith RE/MAX

Showing Results 401 - 440, Page 11 of 18

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