198

Recently Sold Chestertown, MD Homes

Section Image
  • /56

    $759,000 Sold Jul 01, 2025

    7988 Aldan Dr, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 3,394 Sq Ft
    • Built 2000

    Last Sold Summary

    • $224/SF
    • 2 Days On Market

    Current Estimated Value $758,830

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    7988 Aldan Dr, Chestertown, MD 21620
  • /35

    $485,960 Sold Oct 31, 2025

    726 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $229/SF
    • 14 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    726 Aldora Dr, Chestertown, MD 21620
  • /20

    $246,000 Sold Aug 15, 2025

    10624 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Built 1988

    Last Sold Summary

    • $246/SF
    • 17 Days On Market

    Current Estimated Value $241,239

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
  • /53

    $485,000 Sold May 01, 2025

    123 Burchard Sawmill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,648 Sq Ft
    • Built 1918

    Last Sold Summary

    • $294/SF
    • 4 Days On Market

    Current Estimated Value $483,735

    Last Listing Agent Crystal Pickett EXP Realty, LLC

    123 Burchard Sawmill Rd, Chestertown, MD 21620
  • /3

    $675,000 Sold Jun 25, 2025

    213 N Queen St, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,945 Sq Ft
    • Built 1904

    Last Sold Summary

    • $347/SF
    • 2 Days On Market

    Current Estimated Value $668,063

    Last Listing Agent Beth Ostrander Doug Ashley Realtors, LLC

    213 N Queen St, Chestertown, MD 21620
  • /45

    $705,000 Sold Sep 26, 2025

    9194 N Bayview Ave, Chestertown, MD 21620

    • 2 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • Built 1939

    Last Sold Summary

    • $483/SF
    • 19 Days On Market

    Last Listing Agent John Burke Gunther-McClary Real Estate

    9194 N Bayview Ave, Chestertown, MD 21620
  • /43

    $262,500 Sold May 29, 2025

    10705 Millbrook Dr, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 2,106 Sq Ft
    • Built 1988

    Last Sold Summary

    • $125/SF
    • 87 Days On Market

    Current Estimated Value $374,044

    Last Listing Agent Edward Kowalski EXP Realty, LLC

    10705 Millbrook Dr, Chestertown, MD 21620
  • /2

    $1,125,000 Sold Jun 10, 2025

    101 Rivershore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,968 Sq Ft
    • Built 1950

    Last Sold Summary

    • $572/SF

    Current Estimated Value $1,004,039

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    101 Rivershore Rd, Chestertown, MD 21620
  • /18

    $375,000 Sold Oct 10, 2025

    200 Fey Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1996

    Last Sold Summary

    • $239/SF
    • 19 Days On Market

    Last Listing Agent Erik Hoferer Long & Foster Real Estate, Inc.

    200 Fey Rd, Chestertown, MD 21620
  • /23

    $296,337 Sold Sep 30, 2025

    205 Pine St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft
    • Built 1955

    Last Sold Summary

    • $134/SF
    • 32 Days On Market

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, Chestertown, MD 21620
  • /35

    $510,184 Sold May 29, 2025

    716 Aldora Dr, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,120 Sq Ft
    • Built 2025

    Last Sold Summary

    • $241/SF
    • 0 Days On Market

    Last Listing Agent Terri Hill Builder Solutions Realty

    716 Aldora Dr, Chestertown, MD 21620
  • /49

    $960,000 Sold Aug 27, 2025

    10715 Kasota Rd, Chestertown, MD 21620

    • 4 Beds
    • 3 Baths
    • 3,401 Sq Ft
    • Built 2005

    Last Sold Summary

    • $282/SF
    • 5 Days On Market

    Current Estimated Value $958,914

    Last Listing Agent Sarah King Cross Street Realtors LLC

    10715 Kasota Rd, Chestertown, MD 21620
  • /8

    $360,000 Sold Jun 27, 2025

    200 Hoffman Ln, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1957

    Last Sold Summary

    • $319/SF
    • 15 Days On Market

    Current Estimated Value $405,700

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    200 Hoffman Ln, Chestertown, MD 21620
  • /32

    $645,000 Sold Jul 31, 2025

    7682 Waterview Ln, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,240 Sq Ft
    • Built 1989

    Last Sold Summary

    • $288/SF
    • 2 Days On Market

    Current Estimated Value $647,874

    Last Listing Agent Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

    7682 Waterview Ln, Chestertown, MD 21620
  • /10

    $65,000 Sold Aug 11, 2025

    9020 Georgetown Rd, Chestertown, MD 21620

    • Land
    • 2.36 Acres
    • $27,542 per Acre

    Last Sold Summary

    • 54 Days On Market

    Current Estimated Value $64,647

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    9020 Georgetown Rd, Chestertown, MD 21620
  • /10

    $390,000 Sold Feb 06, 2025

    0 Truslow Farm Ln, Chestertown, MD 21620

    • Land
    • 2.3 Acres
    • $169,565 per Acre

    Last Sold Summary

    • 322 Days On Market

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    0 Truslow Farm Ln, Chestertown, MD 21620
  • /37

    $525,000 Sold Jun 30, 2025

    201 Pondview Ct, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 3,016 Sq Ft
    • Built 2001

    Last Sold Summary

    • $174/SF
    • 2 Days On Market

    Current Estimated Value $537,031

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    201 Pondview Ct, Chestertown, MD 21620
  • /40

    $750,000 Sold May 22, 2025

    5594 Langford Bay Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,682 Sq Ft
    • Built 1956

    Last Sold Summary

    • $446/SF
    • 0 Days On Market

    Current Estimated Value $750,648

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    5594 Langford Bay Rd, Chestertown, MD 21620
  • /46

    $425,000 Sold Nov 17, 2025

    201 Boundary Ave, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 3,096 Sq Ft
    • Built 1968

    Last Sold Summary

    • $137/SF
    • 59 Days On Market

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
  • /32

    $360,000 Sold Jun 12, 2025

    216 Silver Heel Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,724 Sq Ft
    • Built 2022

    Last Sold Summary

    • $209/SF
    • 16 Days On Market

    Current Estimated Value $362,191

    Last Listing Agent Cynthia Gardner CENTURY 21 New Millennium

    216 Silver Heel Rd, Chestertown, MD 21620
  • /63

    $535,000 Sold Mar 13, 2025

    209 N Queen St, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,328 Sq Ft
    • Built 1885

    Last Sold Summary

    • $230/SF
    • 10 Days On Market

    Current Estimated Value $600,997

    Last Listing Agent Andrea Alderdice Long & Foster Real Estate, Inc.

    209 N Queen St, Chestertown, MD 21620
  • /26

    $235,000 Sold Aug 07, 2025

    118 Tuxedo Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1975

    Last Sold Summary

    • $223/SF
    • 121 Days On Market

    Current Estimated Value $247,842

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    118 Tuxedo Rd, Chestertown, MD 21620
  • /73

    $850,000 Sold Dec 19, 2025

    492 Pear Tree Point Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 3,720 Sq Ft
    • Built 2001

    Last Sold Summary

    • $228/SF
    • 27 Days On Market

    Last Listing Agent Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    492 Pear Tree Point Rd, Chestertown, MD 21620
  • /31

    $435,000 Sold Nov 03, 2025

    25800 Collins Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft
    • Built 1960

    Last Sold Summary

    • $201/SF
    • 22 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    25800 Collins Ave, Chestertown, MD 21620
  • /10

    $145,000 Sold Oct 14, 2025

    23065 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1957

    Last Sold Summary

    • $123/SF
    • 5 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    23065 Old Fairlee Rd, Chestertown, MD 21620
  • /35

    $600,000 Sold Jan 03, 2025

    101 Landing Ln Unit 39, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 3,300 Sq Ft
    • Built 2013

    Last Sold Summary

    • $182/SF
    • 151 Days On Market

    Current Estimated Value $656,408

    Last Listing Agent Sarah King Cross Street Realtors LLC

    101 Landing Ln Unit 39, Chestertown, MD 21620
  • /25

    $230,000 Sold Nov 20, 2025

    126 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Built 2023

    Last Sold Summary

    • $202/SF
    • 21 Days On Market

    Last Listing Agent Brenda Fornos Taylor Properties

    126 Metcalf Rd, Chestertown, MD 21620
  • /20

    $525,000 Sold Oct 17, 2025

    10165 John Carvill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,774 Sq Ft
    • Built 1987

    Last Sold Summary

    • $189/SF
    • 28 Days On Market

    Last Listing Agent Daniel Hercher Chesapeake Real Estate Associates, LLC

    10165 John Carvill Rd, Chestertown, MD 21620
  • /19

    $335,000 Sold Aug 08, 2025

    10578 Tonopah Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft
    • Built 2025

    Last Sold Summary

    • $223/SF
    • 17 Days On Market

    Current Estimated Value $329,448

    Last Listing Agent David Moore Real Broker, LLC

    10578 Tonopah Rd, Chestertown, MD 21620
  • /36

    $795,000 Sold Nov 07, 2025

    201 Radcliffe Dr, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,736 Sq Ft
    • Built 2011

    Last Sold Summary

    • $291/SF
    • 4 Days On Market

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620
  • /24

    $344,900 Sold Jun 25, 2025

    109 Edmore Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 1993

    Last Sold Summary

    • $257/SF
    • 24 Days On Market

    Current Estimated Value $342,495

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    109 Edmore Rd, Chestertown, MD 21620
  • /37

    $625,000 Sold Jan 02, 2025

    7775 Waterview Ln, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft
    • Built 1937

    Last Sold Summary

    • $351/SF
    • 81 Days On Market

    Current Estimated Value $640,129

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    7775 Waterview Ln, Chestertown, MD 21620
  • /33

    $270,000 Sold Aug 25, 2025

    114 Darden Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft
    • Built 1978

    Last Sold Summary

    • $256/SF
    • 72 Days On Market

    Current Estimated Value $271,831

    Last Listing Agent Lee Wolff FSBO Broker

    114 Darden Rd, Chestertown, MD 21620
  • /22

    $175,000 Sold Jul 25, 2025

    110 Philosophers Terrace, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 896 Sq Ft
    • Built 1955

    Last Sold Summary

    • $195/SF
    • 85 Days On Market

    Current Estimated Value $194,932

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
  • /16

    $195,000 Sold Apr 11, 2025

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,350 Sq Ft
    • Built 1955

    Last Sold Summary

    • $144/SF
    • 0 Days On Market

    Current Estimated Value $199,205

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
  • /36

    $375,000 Sold Aug 13, 2025

    206 Silver Heel Dr, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,302 Sq Ft
    • Built 2022

    Last Sold Summary

    • $163/SF
    • 1 Day On Market

    Last Listing Agent TJ Bennett Samson Properties

    206 Silver Heel Dr, Chestertown, MD 21620
  • /93

    $1,550,000 Sold Nov 07, 2025

    7961 Quaker Neck Rd, Chestertown, MD 21620

    • 5 Beds
    • 4 Baths
    • 4,167 Sq Ft
    • Built 1952

    Last Sold Summary

    • $372/SF
    • 150 Days On Market

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck Rd, Chestertown, MD 21620
  • /21

    $165,300 Sold Mar 05, 2025

    23110 Old Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,545 Sq Ft
    • Built 1938

    Last Sold Summary

    • $107/SF
    • 129 Days On Market

    Last Listing Agent Gina Gargeu Century 21 Downtown

    23110 Old Fairlee Rd, Chestertown, MD 21620
  • /77

    $4,221,800 Sold Nov 24, 2025

    23620 Lands End Rd, Chestertown, MD 21620

    • 5 Beds
    • 8 Baths
    • 9,852 Sq Ft
    • Built 2001

    Last Sold Summary

    • $429/SF
    • 219 Days On Market

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • /44

    $560,000 Sold Apr 21, 2025

    7938 Radcliffe Rd, Chestertown, MD 21620

    • 5 Beds
    • 3.5 Baths
    • 2,408 Sq Ft
    • Built 1976

    Last Sold Summary

    • $233/SF
    • 115 Days On Market

    Current Estimated Value $571,545

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    7938 Radcliffe Rd, Chestertown, MD 21620

Showing Results 121 - 160, Page 4 of 5

How to Buy a Home How to Finance a Home How to Sell a Home