208

Recently Sold Homes in 21620

Section Image
  • 222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    222 Mount Vernon Ave, Chestertown, MD 21620
    /29

    $410,000 Sold Jul 08, 2025

    222 Mount Vernon Ave, Chestertown, MD 21620

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

    Last Sold Summary

    • $248/SF
    • 5 Days On Market

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    222 Mount Vernon Ave, Chestertown, MD 21620
  • 220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    220 Blakefield Dr, Chestertown, MD 21620
    /46

    $474,000 Sold Apr 03, 2025

    220 Blakefield Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2024

    Last Sold Summary

    • $249/SF
    • 84 Days On Market

    Current Estimated Value $496,066

    Last Listing Agent Brenda Fornos Taylor Properties

    220 Blakefield Dr, Chestertown, MD 21620
  • 907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    907 N Meadowview Dr, Chestertown, MD 21620
    /33

    $375,000 Sold Dec 01, 2025

    907 N Meadowview Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,842 Sq Ft
    • Built 2002

    Last Sold Summary

    • $204/SF
    • 83 Days On Market

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, 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

    $609,000 Sold Aug 27, 2025

    10175 John Carvill Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 3,155 Sq Ft
    • Built 1994

    Last Sold Summary

    • $193/SF
    • 11 Days On Market

    Current Estimated Value $612,376

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
  • 225 S Water St Unit 6, Chestertown, MD 21620
    225 S Water St Unit 6, Chestertown, MD 21620
    225 S Water St Unit 6, Chestertown, MD 21620
    /56

    $965,500 Sold Mar 21, 2025

    225 S Water St Unit 6, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • Built 2006

    Last Sold Summary

    • $345/SF
    • 14 Days On Market

    Current Estimated Value $990,721

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    225 S Water St Unit 6, Chestertown, MD 21620
  • 116 Fairview Dr, Chestertown, MD 21620
    116 Fairview Dr, Chestertown, MD 21620
    116 Fairview Dr, Chestertown, MD 21620
    /21

    $305,000 Sold Feb 27, 2025

    116 Fairview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,028 Sq Ft
    • Built 1976

    Last Sold Summary

    • $297/SF
    • 13 Days On Market

    Current Estimated Value $301,083

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    116 Fairview Dr, Chestertown, MD 21620
  • 6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    6744 Church Hill Rd, Chestertown, MD 21620
    /41

    $320,000 Sold Mar 26, 2025

    6744 Church Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,298 Sq Ft
    • Built 1964

    Last Sold Summary

    • $247/SF
    • 199 Days On Market

    Current Estimated Value $329,291

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    6744 Church Hill Rd, Chestertown, MD 21620
  • 209 N Water St, Chestertown, MD 21620
    209 N Water St, Chestertown, MD 21620
    /2

    $1,100,000 Sold Jun 30, 2025

    209 N Water St, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,909 Sq Ft
    • Built 1900

    Last Sold Summary

    • $378/SF
    • 0 Days On Market

    Current Estimated Value $1,148,911

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, Chestertown, MD 21620
  • 720 Aldora Dr Unit 109, Chestertown, MD 21620
    720 Aldora Dr Unit 109, Chestertown, MD 21620
    720 Aldora Dr Unit 109, Chestertown, MD 21620
    /35

    $479,495 Sold Apr 25, 2025

    720 Aldora Dr Unit 109, Chestertown, MD 21620

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

    Last Sold Summary

    • $226/SF
    • 0 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    720 Aldora Dr Unit 109, Chestertown, MD 21620
  • 7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    7483 Shortall St, Chestertown, MD 21620
    /26

    $287,500 Sold Dec 05, 2025

    7483 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 2003

    Last Sold Summary

    • $233/SF
    • 35 Days On Market

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
  • 23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    23628 Canvasback Rd, Chestertown, MD 21620
    /5

    $25,000 Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 0.34 Acre
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
  • 0 Millbrook Dr, Chestertown, MD 21620
    0 Millbrook Dr, Chestertown, MD 21620
    /2

    $9,500 Sold Aug 19, 2025

    0 Millbrook Dr, Chestertown, MD 21620

    • Land
    • 0.5 Acre
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Long & Foster Real Estate, Inc.

    0 Millbrook Dr, Chestertown, MD 21620
  • 0 None Unit MDKE2005014, Chestertown, MD 21620
    0 None Unit MDKE2005014, Chestertown, MD 21620
    /2

    $90,000 Sold May 30, 2025

    0 None Unit MDKE2005014, Chestertown, MD 21620

    • Land
    • 13.46 Acres
    • $6,686 per Acre

    Last Sold Summary

    • 0 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 None Unit MDKE2005014, Chestertown, MD 21620
  • 300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    300 Hilltop Ln, Chestertown, MD 21620
    /20

    $220,000 Sold Sep 22, 2025

    300 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Built 2005

    Last Sold Summary

    • $183/SF
    • 147 Days On Market

    Current Estimated Value $222,902

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • 8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    8978 Orchard Dr, Chestertown, MD 21620
    /44

    $680,000 Sold Sep 30, 2025

    8978 Orchard Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,820 Sq Ft
    • Built 2005

    Last Sold Summary

    • $178/SF
    • 1 Day On Market

    Current Estimated Value $680,593

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
  • 211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    211 David Dr, Chestertown, MD 21620
    /52

    $795,000 Sold Jul 14, 2025

    211 David Dr, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 4,401 Sq Ft
    • Built 1963

    Last Sold Summary

    • $181/SF
    • 2 Days On Market

    Current Estimated Value $790,266

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, Chestertown, MD 21620
  • 0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
    /2

    $2,500 Sold Sep 12, 2025

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678

    • Land
    • 0.34 Acre
    • $7,353 per Acre

    Last Sold Summary

    • 252 Days On Market

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    0 Lots 362 and 363 Klamath Rd, Worton, MD 21678
  • 119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    119 High St, Chestertown, MD 21620
    /60

    $1,165,000 Sold Dec 01, 2025

    119 High St, Chestertown, MD 21620

    • 5 Beds
    • 4.5 Baths
    • 4,409 Sq Ft
    • Built 1876

    Last Sold Summary

    • $264/SF
    • 5 Days On Market

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
  • 109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    109 Secor Rd, Chestertown, MD 21620
    /41

    $385,000 Sold Apr 04, 2025

    109 Secor Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1977

    Last Sold Summary

    • $247/SF
    • 69 Days On Market

    Current Estimated Value $401,063

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    109 Secor Rd, Chestertown, MD 21620
  • 209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    209 Rivershore Rd, Chestertown, MD 21620
    /62

    $790,000 Sold Sep 23, 2025

    209 Rivershore Rd, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,401 Sq Ft
    • Built 1978

    Last Sold Summary

    • $564/SF
    • 32 Days On Market

    Current Estimated Value $778,069

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
  • 100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    100 Metcalf Rd, Chestertown, MD 21620
    /16

    $240,000 Sold Jan 16, 2026

    100 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $211/SF
    • 109 Days On Market

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • 108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    108 N Queen St, Chestertown, MD 21620
    /40

    $600,000 Sold May 16, 2025

    108 N Queen St, Chestertown, MD 21620

    • 5 Beds
    • 2.5 Baths
    • 2,536 Sq Ft
    • Built 1920

    Last Sold Summary

    • $237/SF

    Current Estimated Value $629,898

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, Chestertown, MD 21620
  • 106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    106 Wilton Rd, Chestertown, MD 21620
    /36

    $315,000 Sold Aug 29, 2025

    106 Wilton Rd, Chestertown, MD 21620

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

    Last Sold Summary

    • $298/SF
    • 18 Days On Market

    Current Estimated Value $310,595

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, Chestertown, MD 21620
  • 100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    100 Acorn Dr, Chestertown, MD 21620
    /27

    $280,000 Sold Jun 09, 2025

    100 Acorn Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,930 Sq Ft
    • Built 2004

    Last Sold Summary

    • $145/SF
    • 164 Days On Market

    Current Estimated Value $296,661

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn Dr, Chestertown, MD 21620
  • 8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    8992 S Bayview Dr, Chestertown, MD 21620
    /15

    $155,000 Sold Oct 17, 2025

    8992 S Bayview Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1966

    Last Sold Summary

    • $117/SF
    • 3 Days On Market

    Current Estimated Value $160,935

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
  • 110 Flying Cloud Dr, Chestertown, MD 21620
    110 Flying Cloud Dr, Chestertown, MD 21620
    110 Flying Cloud Dr, Chestertown, MD 21620
    /17

    $335,000 Sold Oct 03, 2025

    110 Flying Cloud Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,856 Sq Ft
    • Built 2023

    Last Sold Summary

    • $180/SF
    • 208 Days On Market

    Current Estimated Value $338,838

    Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
  • 3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    /18

    $636,383 Sold Apr 24, 2025

    3650 Gratitude Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,599 Sq Ft
    • Built 2025

    Last Sold Summary

    • $177/SF
    • 1 Day On Market

    Last Listing Agent Tineshia Johnson NVR, INC.

    3650 Gratitude Way, Chestertown, MD 21620
  • 117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    117 Court St, Chestertown, MD 21620
    /35

    $365,000 Sold Mar 28, 2025

    117 Court St, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 744 Sq Ft
    • Built 1885

    Last Sold Summary

    • $491/SF
    • 23 Days On Market

    Current Estimated Value $372,976

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    117 Court St, Chestertown, MD 21620
  • 310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    310 Hilltop Ln, Chestertown, MD 21620
    /18

    $205,000 Sold Jul 18, 2025

    310 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 2005

    Last Sold Summary

    • $169/SF
    • 24 Days On Market

    Current Estimated Value $215,279

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, Chestertown, MD 21620
  • 898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    898 Washington Ave, Chestertown, MD 21620
    /34

    $237,000 Sold Jun 30, 2025

    898 Washington Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • Built 1967

    Last Sold Summary

    • $171/SF
    • 5 Days On Market

    Current Estimated Value $252,766

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, Chestertown, MD 21620
  • 234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    /3

    $553,500 Sold Apr 07, 2025

    234 Blakefield Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • Built 2024

    Last Sold Summary

    • $231/SF
    • 0 Days On Market

    Current Estimated Value $572,064

    Last Listing Agent Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
  • 8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, Chestertown, MD 21620
    8293 Brices Mill Rd, 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

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    8293 Brices Mill Rd, Chestertown, MD 21620
  • 209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    209 River Rd, Chestertown, MD 21620
    /3

    $124,000 Sold Aug 25, 2025

    209 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $122,772 per Acre

    Last Sold Summary

    • 8 Days On Market

    Current Estimated Value $125,843

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620
  • 26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, Chestertown, MD 21620
    26889 Morgnec Rd, 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 $693,305

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    26889 Morgnec Rd, Chestertown, MD 21620
  • 5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown Rd, Chestertown, MD 21620
    5700 Johnsontown 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

    Last Listing Agent Nicole Stephens Tesla Realty Group, LLC

    5700 Johnsontown Rd, Chestertown, MD 21620
  • 113 Pine Cove Ln, Chestertown, MD 21620
    113 Pine Cove Ln, Chestertown, MD 21620
    /2

    $57,500 Sold Apr 30, 2025

    113 Pine Cove Ln, Chestertown, MD 21620

    • Land
    • 0.45 Acre
    • $127,778 per Acre

    Last Sold Summary

    • 185 Days On Market

    Current Estimated Value $61,500

    Last Listing Agent William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
  • 925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, Chestertown, MD 21620
    925 Round Top Rd, 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 $299,479

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    925 Round Top Rd, Chestertown, MD 21620
  • 22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    22671 Wood Yard Ln, Chestertown, MD 21620
    /4

    $15,000 Sold Jun 02, 2025

    22671 Wood Yard Ln, Chestertown, MD 21620

    • Land
    • 0.48 Acre
    • $31,250 per Acre

    Last Sold Summary

    • 4 Days On Market

    Current Estimated Value $108,688

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    22671 Wood Yard Ln, Chestertown, MD 21620
  • 25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    /53

    $375,000 Sold Apr 16, 2025

    25740 Collins Ave, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,389 Sq Ft
    • Built 1956

    Last Sold Summary

    • $111/SF
    • 29 Days On Market

    Current Estimated Value $405,125

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
  • 8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, Chestertown, MD 21620
    8951 Orchard Dr, 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

    Last Listing Agent Sarah Ulrick Rock Hall Properties Real Estate

    8951 Orchard Dr, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 6

Maryland Kent County Chestertown 21620

Recently Sold Real Estate & Homes in 21620

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group