221

Recently Sold Homes in 21620

Section Image
  • /13

    $615,000

    Sold Aug 27, 2026

    103 Maple Ave, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 4,536 Sq Ft
    • Built 1890

    Last Sold Summary

    • $136/SF
    • 2 Days On Market

    Current Estimated Value $628,355

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    103 Maple Ave, Chestertown, MD 21620
  • /28

    $195,000

    Sold Jul 31, 2026

    139 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1991

    Last Sold Summary

    • 13% Below List Price
    • $162/SF
    • 94 Days On Market

    Current Estimated Value $199,052

    Last Listing Agent Barbara McCaffrey Redfin Corp

    139 Prospect St, Chestertown, MD 21620
  • /34

    $665,000

    Sold Mar 30, 2026

    118 Little Harbor Way Unit 201, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 1% Below List Price
    • $416/SF
    • 8 Days On Market

    Current Estimated Value $639,167

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    118 Little Harbor Way Unit 201, Chestertown, MD 21620
  • /59

    $775,000

    Sold Nov 08, 2025

    8293 Brices Mill Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,836 Sq Ft
    • Built 1900

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Current Estimated Value $778,951

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
  • /2

    $11,000

    Sold Feb 19, 2026

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620

    • Land
    • 2 Acres
    • $5,500 per Acre

    Last Sold Summary

    • 806 Days On Market

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    0 Caulks Field Rd Unit MDKE2002846, Chestertown, MD 21620
  • /19

    $259,900

    Sold May 18, 2026

    107 Metcalfe Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • $217/SF
    • 41 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    107 Metcalfe Rd, Chestertown, MD 21620
  • /23

    $135,000

    Sold Jun 12, 2026

    127 Wood Duck Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,666 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Below List Price
    • $81/SF
    • 7 Days On Market

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    127 Wood Duck Ln, Chestertown, MD 21620
  • /51

    $380,000

    Sold Aug 18, 2026

    107 Flying Cloud Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,534 Sq Ft
    • Built 2023

    Last Sold Summary

    • 4% Below List Price
    • $150/SF
    • 64 Days On Market

    Current Estimated Value $389,447

    Last Listing Agent Cynthia Gardner CENTURY 21 New Millennium

    107 Flying Cloud Dr, Chestertown, MD 21620
  • /47

    $359,000

    Sold Feb 03, 2026

    8833 Georgetown Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • Built 1900

    Last Sold Summary

    • $221/SF
    • 76 Days On Market

    Current Estimated Value $347,894

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown Rd, Chestertown, MD 21620
  • /41

    $324,000

    Sold Aug 14, 2026

    102 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft
    • Built 2023

    Last Sold Summary

    • 5% Below List Price
    • $171/SF
    • 62 Days On Market

    Current Estimated Value $334,973

    Last Listing Agent Dan Foster Long & Foster Real Estate, Inc.

    102 Flying Cloud Dr, Chestertown, MD 21620
  • /32

    $700,000

    Sold Oct 22, 2025

    26889 Morgnec Rd, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,966 Sq Ft
    • Built 1966

    Last Sold Summary

    • $356/SF
    • 156 Days On Market

    Current Estimated Value $723,673

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • /7

    $80,000

    Sold Dec 22, 2025

    5700 Johnsontown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft
    • Built 1900

    Last Sold Summary

    • $70/SF
    • 107 Days On Market

    Current Estimated Value $110,666

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
  • /20

    $125,000

    Sold Mar 02, 2026

    423 Calvert St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1992

    Last Sold Summary

    • $110/SF
    • 112 Days On Market

    Current Estimated Value $179,564

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620
  • /41

    $465,000

    Sold Aug 14, 2026

    311 Devon Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,504 Sq Ft
    • Built 2007

    Last Sold Summary

    • $133/SF
    • 216 Days On Market

    Current Estimated Value $495,143

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    311 Devon Dr, Chestertown, MD 21620
  • /19

    $300,000

    Sold Sep 26, 2025

    925 Round Top Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1977

    Last Sold Summary

    • $284/SF
    • 50 Days On Market

    Current Estimated Value $302,290

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
  • /41

    $330,000

    Sold Mar 31, 2026

    129 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,170 Sq Ft
    • Built 1985

    Last Sold Summary

    • $282/SF
    • 41 Days On Market

    Current Estimated Value $326,773

    Last Listing Agent Roger Boyce Chesapeake Real Estate Associates, LLC

    129 Parma Rd, Chestertown, MD 21620
  • /2

    $325,000

    Sold Jun 17, 2026

    202 Valley Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,427 Sq Ft
    • Built 1956

    Last Sold Summary

    • $228/SF
    • 0 Days On Market

    Current Estimated Value $327,383

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    202 Valley Rd, Chestertown, MD 21620
  • /47

    $700,000

    Sold Dec 04, 2025

    8951 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,735 Sq Ft
    • Built 2014

    Last Sold Summary

    • $187/SF
    • 2 Days On Market

    Current Estimated Value $714,866

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620
  • /12

    $50,000

    Sold Apr 29, 2026

    144 Char Nor Manor Blvd, Chestertown, MD 21620

    • Land
    • 22,651 Sq Ft
    • $96,154 per Acre

    Last Sold Summary

    • 9% Below List Price
    • 6 Days On Market

    Current Estimated Value $53,291

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

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

    $35,000

    Sold Mar 20, 2026

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 14,374 Sq Ft
    • $106,061 per Acre

    Last Sold Summary

    • 756 Days On Market

    Last Listing Agent Vaughn Hogans The Hogans Agency

    0 Elm Rd, Chestertown, MD 21620
  • /2

    $180,000

    Sold Mar 27, 2026

    9925 Flatland Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,368 Sq Ft
    • Built 1900

    Last Sold Summary

    • 26% Above List Price
    • $132/SF

    Current Estimated Value $186,516

    Last Listing Agent Jordan Larigan LPT Realty, LLC

    9925 Flatland Rd, Chestertown, MD 21620
  • /6

    $55,000

    Sold Aug 21, 2026

    110 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,210 Sq Ft
    • Built 1900

    Last Sold Summary

    • 54% Below List Price
    • $25/SF
    • 65 Days On Market

    Current Estimated Value $109,211

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    110 Prospect St, Chestertown, MD 21620
  • /35

    $413,300

    Sold Dec 05, 2025

    600 Rosin Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1976

    Last Sold Summary

    • $318/SF
    • 34 Days On Market

    Current Estimated Value $410,371

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
  • /49

    $392,500

    Sold Jan 28, 2026

    108 Primrose Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,722 Sq Ft
    • Built 1976

    Last Sold Summary

    • 5% Above List Price
    • $228/SF
    • 76 Days On Market

    Current Estimated Value $397,209

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    108 Primrose Rd, Chestertown, MD 21620
  • /2

    $512,500

    Sold Apr 08, 2026

    206 Flyway Ln, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • Built 1996

    Last Sold Summary

    • 3% Above List Price
    • $171/SF
    • 5 Days On Market

    Current Estimated Value $512,056

    Last Listing Agent Kristin Lewis Integrity Real Estate

    206 Flyway Ln, Chestertown, MD 21620
  • /39

    $375,000

    Sold Jan 08, 2026

    7653 Broad Neck Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 1,790 Sq Ft
    • Built 1987

    Last Sold Summary

    • $209/SF
    • 41 Days On Market

    Current Estimated Value $402,578

    Last Listing Agent Brian Petzold Benson & Mangold, LLC

    7653 Broad Neck Rd, Chestertown, MD 21620
  • /47

    $800,000

    Sold Feb 20, 2026

    4671 Cliffs City Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,783 Sq Ft
    • Built 1967

    Last Sold Summary

    • $449/SF

    Current Estimated Value $801,589

    Last Listing Agent John Rolfes Cummings & Co. Realtors

    4671 Cliffs City Rd, Chestertown, MD 21620
  • /27

    $376,000

    Sold May 19, 2026

    136 Hilltop Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • Built 1995

    Last Sold Summary

    • 3% Above List Price
    • $263/SF
    • 5 Days On Market

    Current Estimated Value $375,249

    Last Listing Agent Joie White Northrop Realty

    136 Hilltop Dr, Chestertown, MD 21620
  • /9

    $75,000

    Sold Dec 08, 2025

    109 2nd St, Chestertown, MD 21620

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 49 Days On Market

    Current Estimated Value $128,913

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
  • /67

    $490,000

    Sold May 08, 2026

    100 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 3,799 Sq Ft
    • Built 2008

    Last Sold Summary

    • $129/SF
    • 182 Days On Market

    Current Estimated Value $509,121

    Last Listing Agent Lauren Matera LPT Realty, LLC

    100 Adela Way, Chestertown, MD 21620
  • /19

    $249,000

    Sold Jun 12, 2026

    112 Elm St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,356 Sq Ft
    • Built 1955

    Last Sold Summary

    • 8% Below List Price
    • $184/SF
    • 14 Days On Market

    Current Estimated Value $260,184

    Last Listing Agent Brian Whitaker Coldwell Banker Waterman Realty

    112 Elm St, Chestertown, MD 21620
  • /66

    $868,000

    Sold Oct 15, 2025

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2001

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Current Estimated Value $878,399

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
  • /59

    $392,500

    Sold Oct 30, 2025

    128 Edmore Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft
    • Built 1976

    Last Sold Summary

    • $153/SF
    • 180 Days On Market

    Current Estimated Value $398,940

    Last Listing Agent Lauren Matera LPT Realty, LLC

    128 Edmore Rd, Chestertown, MD 21620
  • /34

    $508,954

    Sold Dec 04, 2025

    730 Aldora Dr Unit 114, Chestertown, MD 21620

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

    Last Sold Summary

    • $198/SF
    • 10 Days On Market

    Last Listing Agent Mrs. Terri E Hill Builder Solutions Realty

    730 Aldora Dr Unit 114, Chestertown, MD 21620
  • /36

    $379,000

    Sold Jan 30, 2026

    104 Iris Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft
    • Built 2006

    Last Sold Summary

    • $223/SF
    • 11 Days On Market

    Current Estimated Value $376,808

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    104 Iris Rd, Chestertown, MD 21620
  • /27

    $290,000

    Sold Jan 16, 2026

    107 Malone Ave, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,200 Sq Ft
    • Built 1962

    Last Sold Summary

    • $242/SF
    • 69 Days On Market

    Current Estimated Value $291,904

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    107 Malone Ave, Chestertown, MD 21620
  • /36

    $270,000

    Sold Feb 19, 2026

    24339 Chestertown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1964

    Last Sold Summary

    • $281/SF
    • 4 Days On Market

    Current Estimated Value $266,107

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    24339 Chestertown Rd, Chestertown, MD 21620
  • /2

    $3,000,000

    Sold Aug 14, 2026

    25440 Learman Rd, Chestertown, MD 21620

    • 3 Beds
    • 4 Baths
    • 3,142 Sq Ft
    • Built 1955

    Last Sold Summary

    • $955/SF
    • 14 Days On Market

    Current Estimated Value $2,159,136

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    25440 Learman Rd, Chestertown, MD 21620
  • /2

    $332,000

    Sold Apr 10, 2026

    23055 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,628 Sq Ft
    • Built 1948

    Last Sold Summary

    • 1% Above List Price
    • $204/SF
    • 5 Days On Market

    Current Estimated Value $326,724

    Last Listing Agent Deborah Callahan Benson & Mangold, LLC

    23055 Old Fairlee Rd, Chestertown, MD 21620
  • /47

    $330,000

    Sold Sep 14, 2026

    8312 Broad Neck Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 3,292 Sq Ft
    • Built 1976

    Last Sold Summary

    • 13% Below List Price
    • $100/SF
    • 14 Days On Market

    Current Estimated Value $419,018

    Last Listing Agent Darrel Reel Pearson Smith Realty, LLC

    8312 Broad Neck Rd, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 6

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