215

Recently Sold Homes in 21620

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  • /2

    $365,000

    Sold Jul 22, 2026

    521 N Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,934 Sq Ft
    • Built 1971

    Last Sold Summary

    • 5% Below List Price
    • $189/SF

    Current Estimated Value $451,404

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    521 N Kent St, Chestertown, MD 21620
  • /21

    $364,900

    Sold Feb 26, 2026

    108 Flying Cloud Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • Built 2023

    Last Sold Summary

    • $188/SF
    • 67 Days On Market

    Current Estimated Value $357,696

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    108 Flying Cloud Dr, Chestertown, MD 21620
  • /24

    $325,000

    Sold Jan 23, 2026

    676 Deep Landing Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,468 Sq Ft
    • Built 2014

    Last Sold Summary

    • $221/SF
    • 2 Days On Market

    Current Estimated Value $325,644

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, Chestertown, MD 21620
  • /79

    $825,000

    Sold May 26, 2026

    25475 Turnberry Ct, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 4,145 Sq Ft
    • Built 2018

    Last Sold Summary

    • 5% Below List Price
    • $199/SF
    • 9 Days On Market

    Current Estimated Value $843,438

    Last Listing Agent Lona Todd Taylor Properties

    25475 Turnberry Ct, 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

    Current Estimated Value $384,391

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview Dr, Chestertown, MD 21620
  • /16

    $150,000

    Sold May 15, 2026

    107 Conley Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 12% Below List Price
    • $132/SF
    • 32 Days On Market

    Current Estimated Value $157,236

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    107 Conley Dr, 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 $628,960

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    10175 John Carvill Rd, Chestertown, MD 21620
  • /16

    $350,000

    Sold Mar 05, 2026

    21111 Texas Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Below List Price
    • $208/SF
    • 17 Days On Market

    Current Estimated Value $354,405

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, Chestertown, MD 21620
  • /2

    $85,000

    Sold Jun 30, 2026

    108 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1957

    Last Sold Summary

    • 40% Below List Price
    • $93/SF
    • 6 Days On Market

    Current Estimated Value $117,450

    Last Listing Agent David Moore Real Broker, LLC

    108 Pine St, Chestertown, MD 21620
  • /43

    $453,000

    Sold Jul 14, 2026

    704 Truslow Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Above List Price
    • $220/SF
    • 22 Days On Market

    Current Estimated Value $439,601

    Last Listing Agent Crystal Smith RE/MAX Executive

    704 Truslow Rd, Chestertown, MD 21620
  • /94

    $1,524,900

    Sold Feb 17, 2026

    10800 Cliff Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 5,241 Sq Ft
    • Built 1997

    Last Sold Summary

    • 2% Above List Price
    • $291/SF
    • 5 Days On Market

    Current Estimated Value $1,475,404

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
  • /48

    $475,900

    Sold Apr 17, 2026

    108 Springbrook Ln, Millington, MD 21651

    • 3 Beds
    • 2 Baths
    • 1,677 Sq Ft
    • Built 2026

    Last Sold Summary

    • $284/SF

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    108 Springbrook Ln, Millington, MD 21651
  • /2

    $395,000

    Sold Jun 25, 2026

    8629 Airy Hill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $274/SF
    • 7 Days On Market

    Current Estimated Value $426,030

    Last Listing Agent Lauren Smith Keller Williams Realty

    8629 Airy Hill Rd, Chestertown, MD 21620
  • /24

    $410,000

    Sold Jun 26, 2026

    109 S College Ave, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,216 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Below List Price
    • $337/SF
    • 71 Days On Market

    Current Estimated Value $410,711

    Last Listing Agent Jeff Guthrie Taylor Properties

    109 S College Ave, Chestertown, MD 21620
  • /36

    $349,500

    Sold Jun 05, 2026

    126 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,304 Sq Ft
    • Built 1971

    Last Sold Summary

    • $268/SF
    • 9 Days On Market

    Current Estimated Value $347,341

    Last Listing Agent Crystal Smith RE/MAX Executive

    126 Char Nor Manor Blvd, 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

    Current Estimated Value $286,604

    Last Listing Agent Christine Johnson RE/MAX Executive

    7483 Shortall St, Chestertown, MD 21620
  • /5

    $25,000

    Sold Nov 14, 2025

    23628 Canvasback Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $73,529 per Acre

    Last Sold Summary

    • 29 Days On Market

    Current Estimated Value $165,667

    Last Listing Agent Christopher McClary Gunther-McClary Real Estate

    23628 Canvasback Rd, Chestertown, MD 21620
  • /10

    $175,000

    Sold Mar 10, 2026

    23069 Raleigh Rd, Chestertown, MD 21620

    • 2 Beds
    • 1,160 Sq Ft
    • Built 1967

    Last Sold Summary

    • $151/SF
    • 184 Days On Market

    Current Estimated Value $191,983

    Last Listing Agent George Mcdowell Keller Williams Select Realtors of Annapolis

    23069 Raleigh Rd, Chestertown, MD 21620
  • /2

    $9,500

    Sold Aug 19, 2025

    0 Millbrook Dr, Chestertown, MD 21620

    • Land
    • 21,780 Sq Ft
    • $19,000 per Acre

    Last Sold Summary

    • 347 Days On Market

    Last Listing Agent Dee Dee Miller Paul Wesley Real Estate

    0 Millbrook Dr, 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 $223,423

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, Chestertown, MD 21620
  • /3

    $7,200

    Sold Jun 04, 2026

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620

    • Land
    • 14,810 Sq Ft
    • $21,176 per Acre

    Last Sold Summary

    • 40% Below List Price
    • 457 Days On Market

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    LOTS 253-254 Carimon Rd, Chestertown, MD 21620
  • /51

    $640,000

    Sold Jul 29, 2026

    7844 Chester Ct, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,248 Sq Ft
    • Built 2005

    Last Sold Summary

    • $197/SF
    • 222 Days On Market

    Current Estimated Value $687,003

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    7844 Chester Ct, 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 $698,829

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard Dr, Chestertown, MD 21620
  • /2

    $2,500

    Sold Sep 12, 2025

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

    • Land
    • 14,810 Sq Ft
    • $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
  • /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

    Current Estimated Value $1,147,980

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    119 High St, Chestertown, MD 21620
  • /23

    $317,000

    Sold Mar 09, 2026

    213 Central Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1984

    Last Sold Summary

    • $257/SF
    • 67 Days On Market

    Current Estimated Value $312,316

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    213 Central Dr, 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 $782,406

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore Rd, Chestertown, MD 21620
  • /34

    $384,000

    Sold Jun 29, 2026

    23416 Cloquet Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • Built 2020

    Last Sold Summary

    • $254/SF
    • 6 Days On Market

    Current Estimated Value $384,117

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23416 Cloquet 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

    Current Estimated Value $245,124

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf Rd, Chestertown, MD 21620
  • /25

    $325,000

    Sold Jul 16, 2026

    10572 Watonga Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 2007

    Last Sold Summary

    • $231/SF
    • 1 Day On Market

    Current Estimated Value $334,458

    Last Listing Agent Samantha Zarnes Serhant

    10572 Watonga Rd, Chestertown, MD 21620
  • /2

    $480,000

    Sold May 04, 2026

    101 Pine Tree Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,848 Sq Ft
    • Built 1993

    Last Sold Summary

    • $260/SF
    • 0 Days On Market

    Current Estimated Value $481,149

    Last Listing Agent Michael Rosendale Rosendale Realty

    101 Pine Tree Rd, Chestertown, MD 21620
  • /16

    $120,000

    Sold Feb 27, 2026

    141 Prospect St, Chestertown, MD 21620

    • 4 Beds
    • 1.5 Baths
    • 1,156 Sq Ft
    • Built 1900

    Last Sold Summary

    • 27% Below List Price
    • $104/SF
    • 33 Days On Market

    Current Estimated Value $137,042

    Last Listing Agent Jeff Guthrie Taylor Properties

    141 Prospect St, 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 $313,578

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, 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 $169,808

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview Dr, Chestertown, MD 21620
  • /18

    $165,000

    Sold Jul 07, 2026

    144 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1.5 Baths
    • 1,082 Sq Ft
    • Built 1900

    Last Sold Summary

    • 8% Below List Price
    • $152/SF
    • 24 Days On Market

    Current Estimated Value $175,512

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    144 Prospect St, 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 $342,352

    Last Listing Agent Sandy Savani Berkshire Hathaway HomeServices Homesale Realty

    110 Flying Cloud Dr, Chestertown, MD 21620
  • /11

    $190,000

    Sold Mar 04, 2026

    0 Hoffecker Rd, Chestertown, MD 21620

    • Land
    • 10.05 Acres
    • $18,905 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 20 Days On Market

    Last Listing Agent Heather Dolan Chesapeake Real Estate Associates, LLC

    0 Hoffecker Rd, Chestertown, MD 21620
  • /19

    $270,000

    Sold Mar 18, 2026

    119 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • Built 1997

    Last Sold Summary

    • 14% Below List Price
    • $190/SF
    • 14 Days On Market

    Current Estimated Value $272,083

    Last Listing Agent Solomon Zaldivar Compass

    119 Darden Rd, Chestertown, MD 21620
  • /62

    $495,000

    Sold Apr 17, 2026

    201 Greenwood Ave, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,984 Sq Ft
    • Built 1960

    Last Sold Summary

    • $124/SF
    • 36 Days On Market

    Current Estimated Value $496,014

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    201 Greenwood Ave, Chestertown, MD 21620
  • /65

    $525,000

    Sold May 29, 2026

    22360 Great Oak Landing Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,688 Sq Ft
    • Built 1989

    Last Sold Summary

    • $195/SF
    • 0 Days On Market

    Current Estimated Value $574,718

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    22360 Great Oak Landing Rd, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 6

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