215

Recently Sold Homes in 21620

Section Image
  • /42

    $260,000

    Sold Feb 18, 2026

    134 Char Nor Manor Blvd, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,128 Sq Ft
    • Built 1954

    Last Sold Summary

    • $230/SF
    • 170 Days On Market

    Current Estimated Value $262,445

    Last Listing Agent John McGlannan Meredith Fine Properties

    134 Char Nor Manor Blvd, Chestertown, MD 21620
  • /13

    $295,000

    Sold Mar 31, 2026

    107 Oak Leaf Dr, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft
    • Built 2004

    Last Sold Summary

    • $152/SF
    • 8 Days On Market

    Current Estimated Value $297,321

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    107 Oak Leaf Dr, Chestertown, MD 21620
  • /14

    $85,000

    Sold Oct 01, 2025

    236 Merganser Dr, Chestertown, MD 21620

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft
    • Built 1973

    Last Sold Summary

    • $94/SF
    • 118 Days On Market

    Current Estimated Value $158,393

    Last Listing Agent Dana Byrd Thurston Wyatt Real Estate, LLC

    236 Merganser Dr, Chestertown, MD 21620
  • /26

    $339,900

    Sold Jun 05, 2026

    21125 Iowa Ave, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,294 Sq Ft
    • Built 1962

    Last Sold Summary

    • $263/SF
    • 54 Days On Market

    Current Estimated Value $334,882

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21125 Iowa Ave, Chestertown, MD 21620
  • /67

    $2,100,000

    Sold Feb 02, 2026

    10121 Fairlee Rd, Chestertown, MD 21620

    • 6 Beds
    • 5 Baths
    • 4,954 Sq Ft
    • Built 1858

    Last Sold Summary

    • $424/SF
    • 58 Days On Market

    Current Estimated Value $2,132,111

    Last Listing Agent Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    10121 Fairlee Rd, Chestertown, MD 21620
  • /46

    $365,000

    Sold Apr 17, 2026

    148 E Step Rd, Chestertown, MD 21620

    • 4 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2022

    Last Sold Summary

    • 2% Below List Price
    • $261/SF
    • 16 Days On Market

    Current Estimated Value $363,510

    Last Listing Agent Norman Lee III Anne Arundel Properties, Inc.

    148 E Step Rd, Chestertown, MD 21620
  • /2

    $749,500

    Sold Apr 13, 2026

    6 Byford Ct, Chestertown, MD 21620

    • 3 Beds
    • 2.5 Baths
    • 3,136 Sq Ft
    • Built 1978

    Last Sold Summary

    • $239/SF
    • 0 Days On Market

    Current Estimated Value $751,731

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    6 Byford Ct, Chestertown, MD 21620
  • /35

    $438,000

    Sold Sep 30, 2025

    206 Barroll Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • Built 1986

    Last Sold Summary

    • $241/SF
    • 52 Days On Market

    Current Estimated Value $441,809

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    206 Barroll Dr, Chestertown, MD 21620
  • /21

    $160,000

    Sold Feb 13, 2026

    21316 Persimmon Dr, Chestertown, MD 21620

    • 2 Beds
    • 1 Bath
    • 1,232 Sq Ft
    • Built 1955

    Last Sold Summary

    • $130/SF
    • 137 Days On Market

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    21316 Persimmon Dr, Chestertown, MD 21620
  • /2

    $1,050,000

    Sold Jun 26, 2026

    231 Richard Dr, Chestertown, MD 21620

    • 5 Beds
    • 3 Baths
    • 2,956 Sq Ft
    • Built 1981

    Last Sold Summary

    • 18% Below List Price
    • $355/SF
    • 86 Days On Market

    Current Estimated Value $1,112,619

    Last Listing Agent Liddy Campbell TTR Sotheby's International Realty

    231 Richard Dr, Chestertown, MD 21620
  • /28

    $322,000

    Sold Nov 14, 2025

    105 Parma Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Built 1992

    Last Sold Summary

    • $261/SF
    • 5 Days On Market

    Current Estimated Value $322,348

    Last Listing Agent Norma Coursey Benson & Mangold, LLC

    105 Parma Rd, Chestertown, MD 21620
  • /38

    $475,000

    Sold Dec 11, 2025

    101 Birch Run Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,961 Sq Ft
    • Built 1979

    Last Sold Summary

    • $242/SF
    • 38 Days On Market

    Current Estimated Value $483,785

    Last Listing Agent Julie Strickler Remax Vision

    101 Birch Run Rd, 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 Mrs. Terri E 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 $238,614

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    10624 Millbrook Dr, Chestertown, MD 21620
  • /56

    $660,000

    Sold Jun 05, 2026

    118 Little Harbor Way Unit 202, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Built 2009

    Last Sold Summary

    • 5% Below List Price
    • $412/SF
    • 83 Days On Market

    Current Estimated Value $659,854

    Last Listing Agent Kaitlyn Collins Benson & Mangold, LLC

    118 Little Harbor Way Unit 202, Chestertown, MD 21620
  • /18

    $220,000

    Sold Apr 14, 2026

    513 Round Top Rd, Chestertown, MD 21620

    • 4 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Below List Price
    • $176/SF
    • 3 Days On Market

    Current Estimated Value $227,394

    Last Listing Agent Ben Garner Cummings & Co. Realtors

    513 Round Top Rd, 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

    Current Estimated Value $694,229

    Last Listing Agent John Burke Gunther-McClary Real Estate

    9194 N Bayview Ave, Chestertown, MD 21620
  • /31

    $340,000

    Sold Mar 19, 2026

    204 Rolling Rd, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 2,296 Sq Ft
    • Built 1975

    Last Sold Summary

    • $148/SF
    • 56 Days On Market

    Current Estimated Value $372,623

    Last Listing Agent Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    204 Rolling Rd, Chestertown, MD 21620
  • /40

    $290,000

    Sold Jun 04, 2026

    115 Acorn Dr, Chestertown, MD 21620

    • 2 Beds
    • 2.5 Baths
    • 1,864 Sq Ft
    • Built 2005

    Last Sold Summary

    • 2% Below List Price
    • $156/SF
    • 11 Days On Market

    Current Estimated Value $294,068

    Last Listing Agent Amy Larrauri Chesapeake Real Estate Associates, LLC

    115 Acorn Dr, Chestertown, MD 21620
  • /3

    $13,000

    Sold Mar 24, 2026

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620

    • Land
    • 3,920 Sq Ft
    • $144,444 per Acre

    Last Sold Summary

    • 699 Days On Market

    Last Listing Agent Cheryl Hurt Coldwell Banker Chesapeake Real Estate Company

    0 Elm St Unit MDKE2003590, Chestertown, MD 21620
  • /37

    $278,500

    Sold May 14, 2026

    107 Longfellow Dr, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • Built 1974

    Last Sold Summary

    • 6% Below List Price
    • 11 Days On Market

    Current Estimated Value $295,980

    Last Listing Agent Doug Ashley Doug Ashley Realtors, LLC

    107 Longfellow Dr, 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

    Current Estimated Value $375,863

    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

    Current Estimated Value $325,426

    Last Listing Agent Herschell Claggett Davis Real Estate, Inc.

    205 Pine St, 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 $1,027,735

    Last Listing Agent Sarah King Cross Street Realtors LLC

    10715 Kasota Rd, Chestertown, MD 21620
  • /30

    $190,000

    Sold Jun 26, 2026

    423 Calvert St, Chestertown, MD 21620

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Above List Price
    • $167/SF
    • 9 Days On Market

    Current Estimated Value $179,564

    Last Listing Agent Ashley Earle Compass

    423 Calvert St, 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 $65,246

    Last Listing Agent Jennifer Mobley Coldwell Banker Chesapeake Real Estate Company

    9020 Georgetown Rd, Chestertown, MD 21620
  • /5

    $15,000

    Sold May 15, 2026

    23698 L Rd, Chestertown, MD 21620

    • Land
    • 2.6 Acres
    • $5,769 per Acre

    Last Sold Summary

    • 48% Below List Price
    • 127 Days On Market

    Current Estimated Value $137,500

    Last Listing Agent Joe Howerton Taylor Properties

    23698 L 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

    Current Estimated Value $432,330

    Last Listing Agent Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    201 Boundary Ave, Chestertown, MD 21620
  • /21

    $255,000

    Sold Jan 16, 2026

    318 Lincoln Dr, Chestertown, MD 21620

    • 3 Beds
    • 2 Baths
    • 960 Sq Ft
    • Built 1966

    Last Sold Summary

    • $266/SF
    • 58 Days On Market

    Current Estimated Value $257,067

    Last Listing Agent Kristina Hyland Coldwell Banker Chesapeake Real Estate Company

    318 Lincoln Dr, 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 $243,966

    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

    Current Estimated Value $867,598

    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

    Current Estimated Value $463,530

    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

    Current Estimated Value $163,466

    Last Listing Agent Retha Arrabal Doug Ashley Realtors, LLC

    23065 Old Fairlee Rd, Chestertown, MD 21620
  • /21

    $215,000

    Sold Jul 21, 2026

    100 Prospect St, Chestertown, MD 21620

    • 3 Beds
    • 1 Bath
    • 1,373 Sq Ft
    • Built 1953

    Last Sold Summary

    • $157/SF
    • 5 Days On Market

    Current Estimated Value $212,252

    Last Listing Agent David Moore Real Broker, LLC

    100 Prospect St, Chestertown, MD 21620
  • /48

    $535,000

    Sold Jul 10, 2026

    9816 Fairlee Rd, Chestertown, MD 21620

    • 3 Beds
    • 3 Baths
    • 1,624 Sq Ft
    • Built 1970

    Last Sold Summary

    • $329/SF
    • 13 Days On Market

    Current Estimated Value $528,792

    Last Listing Agent Scott Hogan Long & Foster Real Estate, Inc.

    9816 Fairlee Rd, 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

    Current Estimated Value $235,653

    Last Listing Agent Brenda Fornos Taylor Properties

    126 Metcalf Rd, Chestertown, MD 21620
  • /68

    $855,000

    Sold Jun 24, 2026

    205 River Rd, Chestertown, MD 21620

    • 4 Beds
    • 2.5 Baths
    • 2,877 Sq Ft
    • Built 2026

    Last Sold Summary

    • 2% Below List Price
    • $297/SF
    • 6 Days On Market

    Current Estimated Value $766,367

    Last Listing Agent Karen Clark Clark & Co Realty, LLC

    205 River 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

    Current Estimated Value $569,825

    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 $330,843

    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

    Current Estimated Value $784,361

    Last Listing Agent Peter Heller Coldwell Banker Chesapeake Real Estate Company

    201 Radcliffe Dr, Chestertown, MD 21620

Showing Results 121 - 160, Page 4 of 6

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