210

Recently Sold Chestertown, MD Homes

Section Image
  • /28

    $264,900

    Sold May 26, 2026

    109 Metcalfe Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2025

    Last Sold Summary

    • $207/SF
    • 124 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    109 Metcalfe Rd, 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 $276,634

    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 $201,053

    Last Listing Agent Debbie Meikle Doug Ashley Realtors, LLC

    110 Philosophers Terrace, Chestertown, MD 21620
  • /37

    $590,000

    Sold Jan 12, 2026

    206 Valley Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 2,869 Sq Ft
    • Built 1957

    Last Sold Summary

    • $206/SF
    • 27 Days On Market

    Current Estimated Value $595,681

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    206 Valley Rd, 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
  • /2

    $300,000

    Sold May 27, 2026

    154 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,408 Sq Ft
    • Built 1975

    Last Sold Summary

    • 5% Below List Price
    • $213/SF
    • 32 Days On Market

    Current Estimated Value $296,107

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    154 Longfellow 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

    Current Estimated Value $1,561,440

    Last Listing Agent Gretchen Wichlinski Compass

    7961 Quaker Neck 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

    Current Estimated Value $4,297,353

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    23620 Lands End Rd, Chestertown, MD 21620
  • /26

    $264,900

    Sold Dec 05, 2025

    101 Metcalfe Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2025

    Last Sold Summary

    • $207/SF
    • 2 Days On Market

    Last Listing Agent David Moore Real Broker, LLC

    101 Metcalfe Rd, Chestertown, MD 21620
  • /2

    $370,000

    Sold May 01, 2026

    217 Philosophers Terrace, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,404 Sq Ft
    • Built 1950

    Last Sold Summary

    • 14% Above List Price
    • $264/SF
    • 3 Days On Market

    Current Estimated Value $335,947

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    217 Philosophers Terrace, Chestertown, MD 21620
  • /24

    $280,000

    Sold Aug 07, 2025

    21363 Indiana Ave, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 896 Sq Ft
    • Built 1955

    Last Sold Summary

    • $312/SF
    • 10 Days On Market

    Current Estimated Value $275,005

    Last Listing Agent Courtney Chipouras TTR Sotheby's International Realty

    21363 Indiana Ave, Chestertown, MD 21620
  • /2

    $14,000

    Sold Sep 05, 2025

    0 Elm Rd, Chestertown, MD 21620

    • Land
    • 9,583 Sq Ft
    • $63,636 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Katie Stecklair Cross Street Realtors LLC

    0 Elm Rd, Chestertown, MD 21620
  • /51

    $361,500

    Sold Dec 19, 2025

    517 High St, Chestertown, MD 21620

    • Studio
    • 1,728 Sq Ft
    • Built 1900

    Last Sold Summary

    • $209/SF
    • 51 Days On Market

    Current Estimated Value $370,777

    Last Listing Agent Kristie Midash L. C. Parker Real Estate

    517 High St, Chestertown, MD 21620
  • /36

    $495,000

    Sold Apr 17, 2026

    515 N Kent St, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,220 Sq Ft
    • Built 1965

    Last Sold Summary

    • $223/SF
    • 1 Day On Market

    Current Estimated Value $491,815

    Last Listing Agent Jody Baker Cross Street Realtors LLC

    515 N Kent St, Chestertown, MD 21620
  • /60

    $725,000

    Sold Aug 05, 2025

    24576 Langford Rd, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 4,023 Sq Ft
    • Built 1989

    Last Sold Summary

    • $180/SF
    • 134 Days On Market

    Current Estimated Value $727,462

    Last Listing Agent Nancy McGuire Maryland Heritage Properties

    24576 Langford Rd, Chestertown, MD 21620
  • /2

    $75,000

    Sold Sep 26, 2025

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620

    • Land
    • 1.49 Acres
    • $50,336 per Acre

    Last Sold Summary

    • 5 Days On Market

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    0 Mcginnes Rd Unit MDQA2014764, Chestertown, MD 21620
  • /34

    $395,000

    Sold Nov 10, 2025

    225 Duke of Kent St, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,850 Sq Ft
    • Built 2000

    Last Sold Summary

    • $214/SF
    • 16 Days On Market

    Current Estimated Value $410,999

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    225 Duke of Kent St, Chestertown, MD 21620
  • /45

    $1,150,000

    Sold Dec 10, 2025

    23393 Cacaway Farm Ln, Chestertown, MD 21620

    • 3 Beds
    • 3.5 Baths
    • 4,446 Sq Ft
    • Built 1990

    Last Sold Summary

    • $259/SF
    • 361 Days On Market

    Current Estimated Value $1,091,541

    Last Listing Agent Ashton Kelley Gunther-McClary Real Estate

    23393 Cacaway Farm Ln, Chestertown, MD 21620
  • /31

    $191,000

    Sold Oct 03, 2025

    21317 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,269 Sq Ft
    • Built 1955

    Last Sold Summary

    • $151/SF
    • 67 Days On Market

    Current Estimated Value $189,573

    Last Listing Agent Michele Palmer Doug Ashley Realtors, LLC

    21317 Persimmon Dr, Chestertown, MD 21620
  • /20

    $155,000

    Sold May 13, 2026

    132 Prospect St, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 910 Sq Ft
    • Built 1949

    Last Sold Summary

    • 22% Below List Price
    • $170/SF
    • 74 Days On Market

    Current Estimated Value $169,423

    Last Listing Agent Matthew Altizer ANR Realty, LLC

    132 Prospect St, Chestertown, MD 21620
  • /39

    $296,500

    Sold May 22, 2026

    108 Oak Leaf Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,867 Sq Ft
    • Built 2004

    Last Sold Summary

    • 1% Below List Price
    • $159/SF
    • 18 Days On Market

    Current Estimated Value $297,215

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    108 Oak Leaf Dr, Chestertown, MD 21620
  • /67

    $424,000

    Sold Jan 30, 2026

    165 Char Nor Manor Blvd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,258 Sq Ft
    • Built 2006

    Last Sold Summary

    • $188/SF
    • 159 Days On Market

    Current Estimated Value $451,551

    Last Listing Agent Crystal Smith RE/MAX Executive

    165 Char Nor Manor Blvd, Chestertown, MD 21620
  • /49

    $905,000

    Sold Nov 14, 2025

    10050 Forrest Ln, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1993

    Last Sold Summary

    • $497/SF
    • 4 Days On Market

    Current Estimated Value $898,250

    Last Listing Agent Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    10050 Forrest Ln, Chestertown, MD 21620
  • /24

    $430,000

    Sold May 29, 2026

    201 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft
    • Built 1980

    Last Sold Summary

    • 1% Below List Price
    • $271/SF
    • 23 Days On Market

    Current Estimated Value $434,129

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    201 Birch Run Rd, Chestertown, MD 21620
  • /2

    $119,500

    Sold Jun 26, 2025

    205 River Rd, Chestertown, MD 21620

    • Land
    • 1.01 Acres
    • $118,317 per Acre

    Last Sold Summary

    • 2 Days On Market

    Current Estimated Value $785,953

    Last Listing Agent Hayley Norris Select Land & Homes, LLC

    205 River Rd, Chestertown, MD 21620
  • /47

    $872,500

    Sold Nov 21, 2025

    10761 Kasota Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 2,582 Sq Ft
    • Built 2005

    Last Sold Summary

    • $338/SF
    • 32 Days On Market

    Current Estimated Value $823,803

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    10761 Kasota Rd, Chestertown, MD 21620
  • /42

    $355,000

    Sold Oct 02, 2025

    127 Char Nor Manor Blvd, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft
    • Built 1963

    Last Sold Summary

    • $427/SF
    • 10 Days On Market

    Current Estimated Value $367,215

    Last Listing Agent Melanie Jones Iron Valley Real Estate of Central PA

    127 Char Nor Manor Blvd, Chestertown, MD 21620
  • /90

    $585,000

    Sold Nov 13, 2025

    103 Adela Way, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 5,576 Sq Ft
    • Built 2008

    Last Sold Summary

    • $105/SF
    • 54 Days On Market

    Current Estimated Value $578,577

    Last Listing Agent Barbara McPhail Douglas Realty LLC

    103 Adela Way, Chestertown, MD 21620
  • /50

    $350,000

    Sold Mar 27, 2026

    10751 Millbrook Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft
    • Built 1975

    Last Sold Summary

    • $180/SF
    • 175 Days On Market

    Current Estimated Value $352,774

    Last Listing Agent Linda Austin Long & Foster Real Estate, Inc.

    10751 Millbrook Dr, Chestertown, MD 21620
  • /29

    $296,500

    Sold Jul 25, 2025

    10670 Tintah Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,404 Sq Ft
    • Built 1999

    Last Sold Summary

    • $211/SF
    • 11 Days On Market

    Current Estimated Value $303,186

    Last Listing Agent Bronwyn Scott Samson Properties

    10670 Tintah Rd, Chestertown, MD 21620
  • /23

    $290,000

    Sold Aug 13, 2025

    107 Dutchess Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • Built 2005

    Last Sold Summary

    • $210/SF
    • 234 Days On Market

    Current Estimated Value $314,538

    Last Listing Agent Jo Ann Edwards The Hogans Agency

    107 Dutchess Rd, Chestertown, MD 21620
  • /63

    $695,000

    Sold May 18, 2026

    10087 John Carvill Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • Built 1983

    Last Sold Summary

    • $444/SF
    • 8 Days On Market

    Current Estimated Value $701,758

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    10087 John Carvill Rd, Chestertown, MD 21620
  • /35

    $650,000

    Sold Mar 10, 2026

    200 Washington Ave, Chestertown, MD 21620

    • 4 Beds
    • 3.5 Baths
    • 2,917 Sq Ft
    • Built 1900

    Last Sold Summary

    • $223/SF
    • 105 Days On Market

    Current Estimated Value $655,609

    Last Listing Agent Richard Keaveney Cross Street Realtors LLC

    200 Washington Ave, Chestertown, MD 21620
  • /73

    $380,000

    Sold Jul 30, 2025

    10705 Millbrook Dr, Chestertown, MD 21620

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

    Last Sold Summary

    • $180/SF
    • 11 Days On Market

    Current Estimated Value $383,607

    Last Listing Agent Adam Murphy RE/MAX Realty Centre, Inc.

    10705 Millbrook Dr, Chestertown, MD 21620
  • /2

    $680,000

    Sold Aug 08, 2025

    100 Little Harbor Way, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 2,204 Sq Ft
    • Built 2015

    Last Sold Summary

    • $309/SF
    • 82 Days On Market

    Current Estimated Value $700,626

    Last Listing Agent Jeannette Westcott Keller Williams Realty Centre

    100 Little Harbor Way, Chestertown, MD 21620
  • /54

    $250,000

    Sold Apr 10, 2026

    112 Metcalf Rd, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft
    • Built 2023

    Last Sold Summary

    • $195/SF
    • 36 Days On Market

    Current Estimated Value $249,778

    Last Listing Agent April Heim Rosendale Realty

    112 Metcalf Rd, Chestertown, MD 21620
  • /41

    $398,000

    Sold Oct 24, 2025

    221 Richard Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,711 Sq Ft
    • Built 1972

    Last Sold Summary

    • $233/SF
    • 3 Days On Market

    Current Estimated Value $402,563

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    221 Richard Dr, Chestertown, MD 21620
  • /32

    $364,000

    Sold Jan 16, 2026

    303 E Campus Ave, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft
    • Built 1963

    Last Sold Summary

    • $238/SF
    • 11 Days On Market

    Current Estimated Value $360,027

    Last Listing Agent Grace Crockett Doug Ashley Realtors, LLC

    303 E Campus Ave, Chestertown, MD 21620
  • /24

    $235,000

    Sold Jan 20, 2026

    7521 Pine Ave, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft
    • Built 1969

    Last Sold Summary

    • $226/SF
    • 12 Days On Market

    Current Estimated Value $246,790

    Last Listing Agent Maryn LeClair Chesapeake Real Estate Associates, LLC

    7521 Pine Ave, Chestertown, MD 21620
  • /9

    $800,000

    Sold Jan 15, 2026

    206 Cannon St, Chestertown, MD 21620

    • Land
    • 1.56 Acres
    • $512,821 per Acre

    Last Sold Summary

    • 635 Days On Market

    Current Estimated Value $806,902

    Last Listing Agent Brian Gearhart Benson & Mangold, LLC

    206 Cannon St, Chestertown, MD 21620

Showing Results 161 - 200, Page 5 of 6

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