216

Recently Sold Homes in 21620

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  • /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 $363,448

    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 $333,366

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    676 Deep Landing Rd, 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

    Current Estimated Value $425,918

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    222 Mount Vernon Ave, 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 $845,087

    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 $381,052

    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 $171,390

    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 $645,961

    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 $353,124

    Last Listing Agent Yvonne Andres Keller Williams Select Realtors of Easton

    21111 Texas Ave, 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 $1,489,844

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, 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 $1,156,728

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water St, 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
  • /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 $347,604

    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 $285,711

    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 $186,667

    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 $187,318

    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 $227,337

    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
  • /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 $706,233

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard 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 $817,732

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David 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 $1,141,574

    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 $316,784

    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 $811,156

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    209 Rivershore 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 $243,755

    Last Listing Agent Dale Hunter Bayside Realty

    100 Metcalf 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 $483,154

    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 $135,028

    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 $324,750

    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 $170,308

    Last Listing Agent William Norris Select Land & Homes, LLC

    8992 S Bayview 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 $352,473

    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 $273,743

    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 $490,279

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    201 Greenwood Ave, 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 $220,577

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, 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 $594,505

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    22360 Great Oak Landing Rd, 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 $259,569

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    898 Washington Ave, 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 $642,743

    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 $777,217

    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
  • /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 $139,842

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 6

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