198

Recently Sold Chestertown, MD Homes

Section Image
  • 600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    600 Rosin Dr, Chestertown, MD 21620
    /35

    $413,300 Sold Dec 05, 2025

    600 Rosin Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • Built 1976

    Last Sold Summary

    • $318/SF
    • 34 Days On Market

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    600 Rosin Dr, Chestertown, MD 21620
  • 0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    0 Fairlee Rd, Chestertown, MD 21620
    /8

    $50,000 Sold May 16, 2025

    0 Fairlee Rd, Chestertown, MD 21620

    • Land
    • 2.2 Acres
    • $22,727 per Acre

    Last Sold Summary

    • 159 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    0 Fairlee Rd, Chestertown, MD 21620
  • 249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    249 Duke of Kent St, Chestertown, MD 21620
    /28

    $343,600 Sold Mar 26, 2025

    249 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,556 Sq Ft
    • Built 2000

    Last Sold Summary

    • $221/SF
    • 14 Days On Market

    Current Estimated Value $349,106

    Last Listing Agent Lee Wolff FSBO Broker

    249 Duke of Kent St, Chestertown, MD 21620
  • 109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    109 2nd St, Chestertown, MD 21620
    /9

    $75,000 Sold Dec 08, 2025

    109 2nd St, Chestertown, MD 21620

    • Land
    • 1.8 Acres
    • $41,667 per Acre

    Last Sold Summary

    • 49 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    109 2nd St, Chestertown, MD 21620
  • 143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    143 Char Nor Manor Blvd, Chestertown, MD 21620
    /66

    $868,000 Sold Oct 15, 2025

    143 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,073 Sq Ft
    • Built 2001

    Last Sold Summary

    • $419/SF
    • 12 Days On Market

    Last Listing Agent Barbara McCaffrey Redfin Corp

    143 Char Nor Manor Blvd, Chestertown, MD 21620
  • 0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
    /2

    $30,000 Sold Aug 29, 2025

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620

    • Land
    • 0.83 Acre
    • $36,145 per Acre

    Last Sold Summary

    • 11 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Georgetown Rd SE Unit MDKE2005448, Chestertown, MD 21620
  • 129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    129 N Queen St, Chestertown, MD 21620
    /38

    $575,000 Sold Jun 06, 2025

    129 N Queen St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,296 Sq Ft
    • Built 1920

    Last Sold Summary

    • $250/SF
    • 19 Days On Market

    Current Estimated Value $572,223

    Last Listing Agent William Norris Select Land & Homes, LLC

    129 N Queen St, Chestertown, MD 21620
  • 128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    128 Edmore Rd, Chestertown, MD 21620
    /59

    $392,500 Sold Oct 30, 2025

    128 Edmore Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,568 Sq Ft
    • Built 1976

    Last Sold Summary

    • $153/SF
    • 180 Days On Market

    Last Listing Agent Lauren Matera Berkshire Hathaway HomeServices PenFed Realty

    128 Edmore Rd, Chestertown, MD 21620
  • 9048 Georgetown Rd, Chestertown, MD 21620
    9048 Georgetown Rd, Chestertown, MD 21620
    /2

    $45,000 Sold Mar 26, 2025

    9048 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 1.21 Acres
    • $37,190 per Acre

    Last Sold Summary

    • 10% Below List Price
    • 713 Days On Market

    Current Estimated Value $51,956

    Last Listing Agent Beverly Sloane Benson & Mangold, LLC

    9048 Georgetown Rd, Chestertown, MD 21620
  • 730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    730 Aldora Dr Unit 114, Chestertown, MD 21620
    /34

    $508,954 Sold Dec 04, 2025

    730 Aldora Dr Unit 114, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,570 Sq Ft
    • Built 2025

    Last Sold Summary

    • $198/SF
    • 10 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    730 Aldora Dr Unit 114, Chestertown, MD 21620
  • 306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    306 Cedar St, Chestertown, MD 21620
    /42

    $312,000 Sold Jun 13, 2025

    306 Cedar St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1959

    Last Sold Summary

    • $222/SF
    • 55 Days On Market

    Current Estimated Value $320,361

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    306 Cedar St, Chestertown, MD 21620
  • 7500 Shortall St, Chestertown, MD 21620
    7500 Shortall St, Chestertown, MD 21620
    7500 Shortall St, Chestertown, MD 21620
    /24

    $299,900 Sold Jan 31, 2025

    7500 Shortall St, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,288 Sq Ft
    • Built 2018

    Last Sold Summary

    • $233/SF
    • 30 Days On Market

    Current Estimated Value $320,680

    Last Listing Agent Lona Todd Taylor Properties

    7500 Shortall St, Chestertown, MD 21620
  • 10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    10724 Foreston Rd, Chestertown, MD 21620
    /35

    $355,675 Sold Feb 28, 2025

    10724 Foreston Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,872 Sq Ft
    • Built 1995

    Last Sold Summary

    • $190/SF
    • 3 Days On Market

    Current Estimated Value $374,241

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10724 Foreston Rd, Chestertown, MD 21620
  • 10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    10061 Flatland Rd, Chestertown, MD 21620
    /21

    $325,000 Sold Mar 06, 2025

    10061 Flatland Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 2,376 Sq Ft
    • Built 1969

    Last Sold Summary

    • $137/SF
    • 18 Days On Market

    Current Estimated Value $335,032

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    10061 Flatland Rd, Chestertown, MD 21620
  • 226 Blakefield Dr, Chestertown, MD 21620
    226 Blakefield Dr, Chestertown, MD 21620
    /2

    $539,000 Sold Mar 31, 2025

    226 Blakefield Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • $225/SF

    Current Estimated Value $548,267

    Last Listing Agent datacorrect BrightMLS Non Subscribing Office

    226 Blakefield Dr, Chestertown, MD 21620
  • 317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    317 Union Church Rd, Chestertown, MD 21620
    /33

    $685,000 Sold Mar 07, 2025

    317 Union Church Rd, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,512 Sq Ft
    • Built 2021

    Last Sold Summary

    • $273/SF
    • 0 Days On Market

    Current Estimated Value $687,806

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    317 Union Church Rd, Chestertown, MD 21620
  • 473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    /24

    $359,900 Sold Apr 11, 2025

    473 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,512 Sq Ft
    • Built 2024

    Last Sold Summary

    • $238/SF
    • 67 Days On Market

    Current Estimated Value $371,529

    Last Listing Agent David Moore Real Broker, LLC

    473 Pear Tree Point Rd, Chestertown, MD 21620
  • 8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    8605 Camp Rd, Chestertown, MD 21620
    /51

    $370,000 Sold May 08, 2025

    8605 Camp Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft
    • Built 1968

    Last Sold Summary

    • $285/SF
    • 10 Days On Market

    Current Estimated Value $378,524

    Last Listing Agent Crystal Smith RE/MAX Executive

    8605 Camp Rd, Chestertown, MD 21620
  • 1814 Pondtown Rd, Chestertown, MD 21620
    1814 Pondtown Rd, Chestertown, MD 21620
    1814 Pondtown Rd, Chestertown, MD 21620
    /8

    $86,000 Sold Jun 09, 2025

    1814 Pondtown Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 973 Sq Ft
    • Built 1974

    Last Sold Summary

    • $88/SF
    • 18 Days On Market

    Current Estimated Value $175,538

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    1814 Pondtown Rd, Chestertown, MD 21620
  • 23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    23370 Lovely Ln, Chestertown, MD 21620
    /31

    $310,000 Sold Sep 30, 2025

    23370 Lovely Ln, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 2009

    Last Sold Summary

    • $185/SF
    • 12 Days On Market

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    23370 Lovely Ln, Chestertown, MD 21620
  • 325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    325 Devon Dr, Chestertown, MD 21620
    /61

    $525,000 Sold Jun 13, 2025

    325 Devon Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 4,086 Sq Ft
    • Built 2011

    Last Sold Summary

    • $128/SF
    • 7 Days On Market

    Current Estimated Value $525,082

    Last Listing Agent Lisa Gambino Berkshire Hathaway HomeServices PenFed Realty

    325 Devon Dr, Chestertown, MD 21620
  • 7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    7729 Country Club Ln, Chestertown, MD 21620
    /18

    $620,000 Sold Oct 27, 2025

    7729 Country Club Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • Built 1989

    Last Sold Summary

    • $272/SF
    • 32 Days On Market

    Last Listing Agent Stacy Kendall Cross Street Realtors LLC

    7729 Country Club Ln, Chestertown, MD 21620
  • 25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    25285 Foxchase Dr, Chestertown, MD 21620
    /39

    $550,000 Sold Jul 01, 2025

    25285 Foxchase Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 1992

    Last Sold Summary

    • $274/SF
    • 3 Days On Market

    Current Estimated Value $555,568

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    25285 Foxchase Dr, Chestertown, MD 21620
  • 107 Char Nor Manor Blvd, Chestertown, MD 21620
    107 Char Nor Manor Blvd, Chestertown, MD 21620
    107 Char Nor Manor Blvd, Chestertown, MD 21620
    /23

    $379,989 Sold Jan 30, 2025

    107 Char Nor Manor Blvd, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,128 Sq Ft
    • Built 1999

    Last Sold Summary

    • $179/SF
    • 56 Days On Market

    Last Listing Agent William Norris Select Land & Homes, LLC

    107 Char Nor Manor Blvd, Chestertown, MD 21620
  • 0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    0 Hoffecker Rd, Chestertown, MD 21620
    /5

    $160,000 Sold Sep 15, 2025

    0 Hoffecker Rd, Chestertown, MD 21620

    • Land
    • 10.05 Acres
    • $15,920 per Acre

    Last Sold Summary

    • 26 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    0 Hoffecker Rd, Chestertown, MD 21620
  • 7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    7071 Pomona Rd, Chestertown, MD 21620
    /47

    $690,000 Sold Aug 25, 2025

    7071 Pomona Rd, Chestertown, MD 21620

    • 4 Beds
    • 4 Baths
    • 2,544 Sq Ft
    • Built 1991

    Last Sold Summary

    • $271/SF
    • 3 Days On Market

    Current Estimated Value $682,263

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7071 Pomona Rd, Chestertown, MD 21620
  • 508 Cannon St, Chestertown, MD 21620
    508 Cannon St, Chestertown, MD 21620
    508 Cannon St, Chestertown, MD 21620
    /20

    $150,000 Sold Jun 06, 2025

    508 Cannon St, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,240 Sq Ft
    • Built 1921

    Last Sold Summary

    • $67/SF
    • 0 Days On Market

    Current Estimated Value $248,305

    Last Listing Agent Deborah Dawkins Coldwell Banker Realty

    508 Cannon St, Chestertown, MD 21620
  • 0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
    /5

    $11,000 Sold May 29, 2025

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

    • Land
    • 0.34 Acre
    • $32,353 per Acre

    Last Sold Summary

    • 371 Days On Market

    Last Listing Agent Adam Shpritz Ashland Auction Group LLC

    0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
  • 111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    111 Cee Jay Rd, Chestertown, MD 21620
    /38

    $349,000 Sold Oct 16, 2025

    111 Cee Jay Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2021

    Last Sold Summary

    • $249/SF
    • 10 Days On Market

    Last Listing Agent Michelle Abplanalp Rosendale Realty

    111 Cee Jay Rd, Chestertown, MD 21620
  • 10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    10575 Hyala Ct, Chestertown, MD 21620
    /22

    $359,000 Sold Jul 31, 2025

    10575 Hyala Ct, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,978 Sq Ft
    • Built 2003

    Last Sold Summary

    • $181/SF
    • 5 Days On Market

    Current Estimated Value $354,330

    Last Listing Agent Laura Anthony Benson & Mangold, LLC

    10575 Hyala Ct, Chestertown, MD 21620
  • 304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    304 Hilltop Ln, Chestertown, MD 21620
    /31

    $215,000 Sold Sep 26, 2025

    304 Hilltop Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,199 Sq Ft
    • Built 2005

    Last Sold Summary

    • $179/SF
    • 34 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    304 Hilltop Ln, Chestertown, MD 21620
  • 9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    9190 N Bayview Ave, Chestertown, MD 21620
    /38

    $285,000 Sold Sep 05, 2025

    9190 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • Built 1969

    Last Sold Summary

    • $246/SF
    • 12 Days On Market

    Current Estimated Value $298,697

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    9190 N Bayview Ave, Chestertown, MD 21620
  • 110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    110 S Mill St, Chestertown, MD 21620
    /39

    $695,000 Sold Nov 05, 2025

    110 S Mill St, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 2,492 Sq Ft
    • Built 1900

    Last Sold Summary

    • $279/SF
    • 7 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    110 S Mill St, Chestertown, MD 21620
  • 107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    /19

    $230,000 Sold May 01, 2025

    107 Chester Arms Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2022

    Last Sold Summary

    • $202/SF
    • 14 Days On Market

    Current Estimated Value $242,617

    Last Listing Agent Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, Chestertown, MD 21620
  • 0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
    /12

    $162,000 Sold Nov 10, 2025

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620

    • Land
    • 5.34 Acres
    • $30,337 per Acre

    Last Sold Summary

    • 64 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    0 Church Hill ( Lot 2) Rd, Chestertown, MD 21620
  • 22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    22570 Bay Shore Rd, Chestertown, MD 21620
    /73

    $435,000 Sold Sep 30, 2025

    22570 Bay Shore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • Built 2003

    Last Sold Summary

    • $243/SF
    • 42 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    22570 Bay Shore Rd, Chestertown, MD 21620
  • 10640 Watonga Rd, Chestertown, MD 21620
    10640 Watonga Rd, Chestertown, MD 21620
    10640 Watonga Rd, Chestertown, MD 21620
    /31

    $305,000 Sold Apr 01, 2025

    10640 Watonga Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,196 Sq Ft
    • Built 1995

    Last Sold Summary

    • $255/SF
    • 2 Days On Market

    Current Estimated Value $308,477

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    10640 Watonga Rd, Chestertown, MD 21620
  • 118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    118 Char Nor Manor Blvd, Chestertown, MD 21620
    /34

    $265,000 Sold May 02, 2025

    118 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,114 Sq Ft
    • Built 1965

    Last Sold Summary

    • $238/SF
    • 120 Days On Market

    Current Estimated Value $277,367

    Last Listing Agent Rylie Patrick Chesapeake Real Estate Associates, LLC

    118 Char Nor Manor Blvd, Chestertown, MD 21620
  • 212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    212 Landing Ln, Chestertown, MD 21620
    /36

    $750,000 Sold Dec 01, 2025

    212 Landing Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • Built 2024

    Last Sold Summary

    • 238 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    212 Landing Ln, Chestertown, MD 21620
  • 104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    104 Dutchess Rd, Chestertown, MD 21620
    /23

    $312,000 Sold Jun 20, 2025

    104 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft
    • Built 1989

    Last Sold Summary

    • $263/SF
    • 21 Days On Market

    Current Estimated Value $320,104

    Last Listing Agent Helen J Butler Taylor Properties

    104 Dutchess Rd, Chestertown, MD 21620

Showing Results 41 - 80, Page 2 of 5

Maryland Kent County Chestertown

Recently Sold Real Estate & Homes in Chestertown, MD

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