221

Recently Sold Homes in 21620

Section Image
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /17

    $112,500

    Sold Jun 09, 2026

    21324 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1955

    Last Sold Summary

    • 26% Below List Price
    • $91/SF
    • 63 Days On Market

    Current Estimated Value $130,864

    Last Listing Agent JT Powell Coldwell Banker Realty - Washington

    21324 Persimmon Dr, 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
  • /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
  • /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
  • /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
  • /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 $1,578,443

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck 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 $4,272,972

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End 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
  • /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
  • /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
  • /40

    $220,000

    Sold May 18, 2026

    1517 Dudley Corners Rd, Millington, MD 21651

    • 6 Beds
    • 3 Baths
    • 2,948 Sq Ft
    • Built 1961

    Last Sold Summary

    • 34% Below List Price
    • $75/SF
    • 24 Days On Market

    Current Estimated Value $277,587

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    1517 Dudley Corners Rd, Millington, MD 21651
  • /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
  • /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
  • /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 $374,510

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

    517 High St, Chestertown, MD 21620
  • /49

    $460,000

    Sold Sep 03, 2026

    105 N Water St Unit 2, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,011 Sq Ft
    • Built 1900

    Last Sold Summary

    • 3% Below List Price
    • $455/SF
    • 22 Days On Market

    Last Listing Agent Missy Miller Aldave Northrop Realty

    105 N Water St Unit 2, 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 $493,279

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    515 N Kent St, 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
  • /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 $400,574

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
  • /24

    $141,000

    Sold Sep 03, 2026

    207 Lincoln Dr, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,152 Sq Ft
    • Built 1965

    Last Sold Summary

    • 4% Above List Price
    • $122/SF
    • 4 Days On Market

    Current Estimated Value $240,008

    Last Listing Agent Jennifer Cernik Monument Sotheby's International Realty

    207 Lincoln Dr, 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 $1,179,198

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, 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 $231,877

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    221 Dutchess Rd, Chestertown, MD 21620
  • /31

    $191,000

    Sold Oct 03, 2025

    21317 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,269 Sq Ft
    • Built 1955

    Last Sold Summary

    • $151/SF
    • 67 Days On Market

    Current Estimated Value $190,061

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
  • /20

    $155,000

    Sold May 13, 2026

    132 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1949

    Last Sold Summary

    • 22% Below List Price
    • $170/SF
    • 74 Days On Market

    Current Estimated Value $156,409

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • /39

    $296,500

    Sold May 22, 2026

    108 Oak Leaf Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,867 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $159/SF
    • 18 Days On Market

    Current Estimated Value $299,380

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    108 Oak Leaf Dr, Chestertown, MD 21620
  • /67

    $424,000

    Sold Jan 30, 2026

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft
    • Built 2006

    Last Sold Summary

    • $188/SF
    • 159 Days On Market

    Current Estimated Value $443,019

    Last Listing Agent Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • /2

    $365,000

    Sold Jul 13, 2026

    23264 Clarissa Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 2021

    Last Sold Summary

    • $292/SF
    • 4 Days On Market

    Current Estimated Value $363,234

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    23264 Clarissa Rd, Chestertown, MD 21620
  • /88

    $335,320

    Sold Aug 18, 2026

    22481 Goose Hollow Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1984

    Last Sold Summary

    • 20% Above List Price
    • $259/SF
    • 22 Days On Market

    Current Estimated Value $309,473

    Last Listing Agent Tom Atwood Keller Williams Legacy

    22481 Goose Hollow Dr, Chestertown, MD 21620
  • /49

    $905,000

    Sold Nov 14, 2025

    10050 Forrest Ln, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1993

    Last Sold Summary

    • $497/SF
    • 4 Days On Market

    Current Estimated Value $902,217

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
  • /24

    $430,000

    Sold May 29, 2026

    201 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $271/SF
    • 23 Days On Market

    Current Estimated Value $438,767

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • /47

    $872,500

    Sold Nov 21, 2025

    10761 Kasota Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,582 Sq Ft
    • Built 2005

    Last Sold Summary

    • $338/SF
    • 32 Days On Market

    Current Estimated Value $799,853

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
  • /29

    $525,000

    Sold Jun 26, 2026

    1014 Twin Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,817 Sq Ft
    • Built 2017

    Last Sold Summary

    • 5% Above List Price
    • $289/SF
    • 0 Days On Market

    Current Estimated Value $503,112

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    1014 Twin Ct, Chestertown, MD 21620
  • /42

    $355,000

    Sold Oct 02, 2025

    127 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • Built 1963

    Last Sold Summary

    • $427/SF
    • 10 Days On Market

    Current Estimated Value $360,114

    Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

    127 Char Nor Manor Blvd, Chestertown, MD 21620
  • /90

    $585,000

    Sold Nov 13, 2025

    103 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft
    • Built 2008

    Last Sold Summary

    • $105/SF
    • 54 Days On Market

    Current Estimated Value $591,092

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 6

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