205

Recently Sold Chestertown, MD Homes

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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 $364,294

    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 $327,132

    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 $444,761

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    222 Mount Vernon Ave, 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 $378,947

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    907 N Meadowview 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 $639,971

    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 $365,994

    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 $1,484,391

    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 $1,158,489

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    209 N Water 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

    Current Estimated Value $284,668

    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 $184,667

    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 $186,360

    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
  • /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
  • /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 $226,030

    Last Listing Agent William Sutton Coldwell Banker Chesapeake Real Estate Company

    300 Hilltop Ln, 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 $696,265

    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 $817,511

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    211 David Dr, 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

    Current Estimated Value $1,155,286

    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 $319,453

    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 $803,664

    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 $240,370

    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 $476,168

    Last Listing Agent Michael Rosendale Rosendale Realty

    101 Pine Tree Rd, 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 $650,049

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    108 N Queen St, 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 $165,092

    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 $321,288

    Last Listing Agent Crystal Smith RE/MAX Executive

    106 Wilton Rd, 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 $299,695

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    100 Acorn 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 $173,232

    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 $346,259

    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 $277,940

    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 $504,329

    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 $219,859

    Last Listing Agent Clint Evans Cross Street Realtors LLC

    310 Hilltop Ln, 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 $258,380

    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 $647,847

    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 $782,617

    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 $128,400

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    209 River Rd, 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 $352,490

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    8833 Georgetown 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 $706,036

    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 $137,102

    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 $134,808

    Last Listing Agent Barbara McCaffrey Redfin Corp

    423 Calvert St, Chestertown, MD 21620

Showing Results 1 - 40, Page 1 of 6

Frequently Asked Questions

What is the average home price in Chestertown, MD?
Homes for sale in Chestertown, MD have an average home price of $462,371.
What is the average time to sell a house in Chestertown, MD?
The houses for sale in Chestertown, MD spend an average of 49 days on the market.
What is the number of active homes for sale in Chestertown, MD?
There are 34 active homes for sale in Chestertown, MD.
How many homes have sold over the last 12 months in Chestertown, MD?
98 homes have sold in Chestertown, MD over the last 12 months.

Home Trends in Chestertown, MD

Housing Trends

Median Sale Price
$377,000
Median Single Family Sale Price
$415,000
Median Townhouse Sale Price
$295,000
Median 2 Bedroom Sale Price
$375,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$212
Number of Homes for Sale
34
Last 12 months Home Sales
98
Months of Supply
4.20
Median List Price
$396,500
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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