221

Recently Sold Homes in 21620

Section Image
  • /29

    $330,000

    Sold Apr 03, 2026

    23110 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,805 Sq Ft
    • Built 1938

    Last Sold Summary

    • $183/SF
    • 174 Days On Market

    Current Estimated Value $321,904

    Last Listing Agent Thomas Huston Real Broker LLC

    23110 Old Fairlee Rd, Chestertown, MD 21620
  • /6

    $5,000

    Sold Jan 08, 2026

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620

    • Land
    • 18,295 Sq Ft
    • $11,905 per Acre

    Last Sold Summary

    • 230 Days On Market

    Last Listing Agent Andrew Meikle Doug Ashley Realtors, LLC

    0 Lot 24 & 25 Buck Neck Rd Unit MDKE2004828, Chestertown, MD 21620
  • /47

    $355,000

    Sold May 26, 2026

    349 & 351 High St, Chestertown, MD 21620

    • Studio
    • 3,664 Sq Ft
    • Built 1900

    Last Sold Summary

    • $97/SF
    • 496 Days On Market

    Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    349 & 351 High St, Chestertown, MD 21620
  • /25

    $334,000

    Sold Apr 06, 2026

    8750 Georgetown Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 2014

    Last Sold Summary

    • $176/SF
    • 134 Days On Market

    Current Estimated Value $345,868

    Last Listing Agent Mikeshia Lindsey Chesapeake Real Estate Associates, LLC

    8750 Georgetown Rd, Chestertown, MD 21620
  • /49

    $552,000

    Sold Apr 17, 2026

    216 Blakefield Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $230/SF
    • 94 Days On Market

    Current Estimated Value $553,966

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    216 Blakefield Dr, Chestertown, MD 21620
  • /15

    $555,000

    Sold Jan 12, 2026

    26933 Mallard Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 1956

    Last Sold Summary

    • $347/SF
    • 77 Days On Market

    Current Estimated Value $569,669

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    26933 Mallard Rd, Chestertown, MD 21620
  • /31

    $310,000

    Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Current Estimated Value $314,902

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
  • /72

    $1,200,000

    Sold Aug 14, 2026

    202 Royston Shores Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 1968

    Last Sold Summary

    • $524/SF
    • 16 Days On Market

    Current Estimated Value $1,175,998

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    202 Royston Shores Rd, Chestertown, MD 21620
  • /18

    $620,000

    Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Current Estimated Value $636,337

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
  • /12

    $146,000

    Sold Sep 08, 2026

    7224 Rock Hall Rd, Rock Hall, MD 21661

    • Land
    • 2.15 Acres
    • $67,907 per Acre

    Last Sold Summary

    • 320 Days On Market

    Current Estimated Value $156,729

    Last Listing Agent Cindy Genther Rock Hall Properties Real Estate

    7224 Rock Hall Rd, Rock Hall, MD 21661
  • /41

    $740,000

    Sold Jan 15, 2026

    10230 John Carvill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,350 Sq Ft
    • Built 1775

    Last Sold Summary

    • $315/SF
    • 30 Days On Market

    Current Estimated Value $759,066

    Last Listing Agent Robert G. Shannahan Shoreline Realty

    10230 John Carvill Rd, Chestertown, MD 21620
  • /2

    $325,000

    Sold Jan 30, 2026

    303 Cedar St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,577 Sq Ft
    • Built 1985

    Last Sold Summary

    • 3% Below List Price
    • $126/SF
    • 4 Days On Market

    Current Estimated Value $357,407

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    303 Cedar St, Chestertown, MD 21620
  • /40

    $293,000

    Sold Jun 08, 2026

    301 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Built 1966

    Last Sold Summary

    • 5% Below List Price
    • $254/SF
    • 54 Days On Market

    Current Estimated Value $293,876

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    301 Lincoln Dr, Chestertown, MD 21620
  • /2

    $339,900

    Sold Apr 21, 2026

    103 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2023

    Last Sold Summary

    • $197/SF
    • 0 Days On Market

    Current Estimated Value $339,854

    Last Listing Agent Laura Snyder American Premier Realty, LLC

    103 Flying Cloud Dr, Chestertown, MD 21620
  • /42

    $316,000

    Sold Sep 01, 2026

    10720 Foreston Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft
    • Built 1963

    Last Sold Summary

    • 6% Below List Price
    • $224/SF
    • 31 Days On Market

    Current Estimated Value $324,514

    Last Listing Agent Kathleen Eder Compass

    10720 Foreston Rd, Chestertown, MD 21620
  • /32

    $365,000

    Sold May 29, 2026

    2032 Pondtown Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • Built 2007

    Last Sold Summary

    • 12% Above List Price
    • $326/SF
    • 9 Days On Market

    Current Estimated Value $349,305

    Last Listing Agent Joie White Northrop Realty

    2032 Pondtown Rd, Chestertown, MD 21620
  • /38

    $349,000

    Sold Oct 16, 2025

    111 Cee Jay Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2021

    Last Sold Summary

    • $249/SF
    • 10 Days On Market

    Current Estimated Value $357,065

    Last Listing Agent Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
  • /28

    $205,000

    Sold Jul 02, 2026

    21363 Lynn Ln, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,314 Sq Ft
    • Built 1955

    Last Sold Summary

    • $156/SF
    • 5 Days On Market

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    21363 Lynn Ln, Chestertown, MD 21620
  • /39

    $500,000

    Sold Sep 01, 2026

    101 S Mill St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,476 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $339/SF
    • 36 Days On Market

    Current Estimated Value $506,699

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 S Mill St, Chestertown, MD 21620
  • /29

    $433,000

    Sold Sep 01, 2026

    222 Mount Vernon Ave, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,656 Sq Ft
    • Built 1916

    Last Sold Summary

    • $261/SF
    • 273 Days On Market

    Current Estimated Value $418,024

    Last Listing Agent Kellie Gough McLendon Long & Foster Real Estate, Inc.

    222 Mount Vernon Ave, Chestertown, MD 21620
  • /31

    $215,000

    Sold Sep 26, 2025

    304 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft
    • Built 2005

    Last Sold Summary

    • $179/SF
    • 34 Days On Market

    Current Estimated Value $222,520

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
  • /20

    $320,000

    Sold Jul 08, 2026

    10584 Klamath Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    10584 Klamath Rd, Chestertown, MD 21620
  • /39

    $695,000

    Sold Nov 05, 2025

    110 S Mill St, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 7 Days On Market

    Current Estimated Value $688,935

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
  • /70

    $620,000

    Sold Apr 20, 2026

    11040 Kylie Ln, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,684 Sq Ft
    • Built 2000

    Last Sold Summary

    • $168/SF
    • 497 Days On Market

    Current Estimated Value $635,508

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    11040 Kylie Ln, Chestertown, MD 21620
  • /12

    $162,000

    Sold Nov 10, 2025

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620

    • Land
    • 5.34 Acres
    • $30,337 per Acre

    Last Sold Summary

    • 64 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
  • /73

    $435,000

    Sold Sep 30, 2025

    22570 Bay Shore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • Built 2003

    Last Sold Summary

    • $243/SF
    • 42 Days On Market

    Current Estimated Value $450,145

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
  • /32

    $415,000

    Sold Jan 07, 2026

    411 Greenwood Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,676 Sq Ft
    • Built 2003

    Last Sold Summary

    • $248/SF
    • 1 Day On Market

    Current Estimated Value $422,072

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    411 Greenwood Ave, Chestertown, MD 21620
  • /36

    $750,000

    Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
  • /63

    $1,350,000

    Sold Sep 22, 2025

    21082 Wyoming Ave, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,699 Sq Ft
    • Built 1965

    Last Sold Summary

    • $500/SF
    • 104 Days On Market

    Current Estimated Value $1,330,551

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21082 Wyoming Ave, Chestertown, MD 21620
  • /24

    $455,000

    Sold Oct 21, 2025

    224 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1978

    Last Sold Summary

    • $241/SF
    • 13 Days On Market

    Current Estimated Value $466,142

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    224 Valley Rd, Chestertown, MD 21620
  • /28

    $289,000

    Sold Aug 21, 2026

    517 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1960

    Last Sold Summary

    • 17% Below List Price
    • $232/SF
    • 41 Days On Market

    Current Estimated Value $307,743

    Last Listing Agent Barry Hess Keller Williams Flagship

    517 Round Top Rd, Chestertown, MD 21620
  • /31

    $250,000

    Sold Nov 11, 2025

    124 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,024 Sq Ft
    • Built 1967

    Last Sold Summary

    • $244/SF
    • 2 Days On Market

    Current Estimated Value $259,514

    Last Listing Agent Crystal Smith RE/MAX Executive

    124 Char Nor Manor Blvd, Chestertown, MD 21620
  • /8

    $75,000

    Sold Aug 13, 2026

    0 East St, Chestertown, MD 21620

    • Land
    • 20,908 Sq Ft
    • $156,250 per Acre

    Last Sold Summary

    • 50 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 East St, Chestertown, MD 21620
  • /19

    $354,900

    Sold Nov 10, 2025

    2010 Mcginnes Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,253 Sq Ft
    • Built 1962

    Last Sold Summary

    • $283/SF
    • 14 Days On Market

    Current Estimated Value $360,363

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    2010 Mcginnes Rd, Chestertown, MD 21620
  • /29

    $359,900

    Sold Nov 24, 2025

    221 Old Bridge Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • Built 1924

    Last Sold Summary

    • $194/SF
    • 26 Days On Market

    Current Estimated Value $364,289

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    221 Old Bridge Rd, Chestertown, MD 21620
  • /30

    $1,100,000

    Sold Jan 16, 2026

    300 Hickory Ln, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • Built 1940

    Last Sold Summary

    • $302/SF
    • 163 Days On Market

    Current Estimated Value $1,129,907

    Last Listing Agent John Burke Gunther-McClary Real Estate

    300 Hickory Ln, Chestertown, MD 21620
  • /2

    $1,650,000

    Sold Jun 30, 2026

    114 Chester View, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • Built 1960

    Last Sold Summary

    • $799/SF
    • 0 Days On Market

    Current Estimated Value $1,177,591

    Last Listing Agent Jack Boniface Cross Street Realtors LLC

    114 Chester View, Chestertown, MD 21620
  • /65

    $455,000

    Sold Apr 13, 2026

    206 Camelot Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,186 Sq Ft
    • Built 2009

    Last Sold Summary

    • 13% Below List Price
    • $208/SF
    • 30 Days On Market

    Current Estimated Value $464,468

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    206 Camelot Dr, Chestertown, MD 21620
  • /43

    $379,900

    Sold Jan 21, 2026

    112 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,615 Sq Ft
    • Built 2023

    Last Sold Summary

    • $145/SF
    • 27 Days On Market

    Current Estimated Value $391,610

    Last Listing Agent Federico Busacca EXP Realty, LLC

    112 Silver Heel Dr, Chestertown, MD 21620
  • /38

    $474,990

    Sold May 18, 2026

    728 Aldora Dr Unit 113, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • $185/SF
    • 286 Days On Market

    Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

    728 Aldora Dr Unit 113, Chestertown, MD 21620

Showing Results 81 - 120, Page 3 of 6

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