206

Recently Sold Chestertown, MD Homes

Section Image
  • /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 $444,216

    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 $361,480

    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 $334,874

    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 $830,284

    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 $382,771

    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 $641,207

    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 $447,484

    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 $1,493,924

    Last Listing Agent Lona Todd Taylor Properties

    10800 Cliff Rd, Chestertown, MD 21620
  • /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 $428,003

    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 $410,642

    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 $346,340

    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 $285,938

    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 $125,000

    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 $190,890

    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 $225,524

    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 $702,071

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    8978 Orchard 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 $1,153,904

    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 $315,898

    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 $802,288

    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 $385,938

    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 $246,216

    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 $326,690

    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 $480,030

    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 $206,734

    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 $156,981

    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 $342,146

    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 $493,901

    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 $575,137

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    22360 Great Oak Landing Rd, 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

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 $431,380.
What is the average time to sell a house in Chestertown, MD?
The houses for sale in Chestertown, MD spend an average of 42 days on the market.
What is the number of active homes for sale in Chestertown, MD?
There are 29 active homes for sale in Chestertown, MD.
How many homes have sold over the last 12 months in Chestertown, MD?
94 homes have sold in Chestertown, MD over the last 12 months.

Home Price Trends

Median Sale Price
$364,450
Median Single Family Sale Price
$375,000
Median Townhouse Sale Price
$264,900
Median 2 Bedroom Sale Price
$315,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$210
Number of Homes for Sale
29
Last 12 months Home Sales
94
Months of Supply
3.70
Median List Price
$364,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-3%
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