Recently Viewed Properties
102 Results

21620 Recent Home Sales

Add

Oops! We need you to add a location.
more
Selecting these elements will cause content on the page to be updated. Near by
NEARBY
    Selecting these elements will cause content on the page to be updated. History
    HISTORY
      Filters
      Selection will refresh the page with new results. properties
      —
      Selection will refresh the page with new results.
      Selection will refresh the page with new results. properties
      Property Type
      PRICE
      to
      BEDROOMS
      BATHROOMS
      STATUS (only include)
      Lot Sizeto
      FEATURES

      Add

      Max keywords reached
      Hide Map
      Order By
      102 Results
      Order By

      Use previous and next buttons to navigate

      407 High St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      407 High St  Chestertown, MD 21620

      $725,000
      • Single Family
      • Closed
      • MLS # MDKE2006496
      • Updated 10 hours ago
      • 3
        Beds
      • 4
        Full Baths
      • 1
        Partial Bath
      • 5
        Total Baths
      • 3,047
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Lisa P Raffetto
      Sold by Cross Street Realtors LLC, Richard Keaveney

      Use previous and next buttons to navigate

      207 Lincoln Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      207 Lincoln Dr  Chestertown, MD 21620

      $141,000
      • Single Family
      • Closed
      • MLS # MDKE2006894
      • Updated 5 days ago
      • 4
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,152
        Sq. Ft.
      Listed by Monument Sotheby's International Realty, Jennifer C Cernik
      Sold by Monument Sotheby's International Realty, Christopher John Blizzard

      Use previous and next buttons to navigate

      10720 Foreston Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      10720 Foreston Rd  Chestertown, MD 21620

      $316,000
      • Single Family
      • Closed
      • MLS # MDKE2006800
      • Updated 6 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,412
        Sq. Ft.
      • 1
        Car Garage
      Listed by Compass, Kathleen M Eder
      Sold by Taylor Properties, Jeff Guthrie

      Use previous and next buttons to navigate

      222 Mt Vernon Ave, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      222 Mt Vernon Ave  Chestertown, MD 21620

      $433,000
      • Single Family
      • Closed
      • MLS # MDKE2005876
      • Updated 5 days ago
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,656
        Sq. Ft.
      Listed by Long & Foster Real Estate, Inc., Kellie Gough McLendon and Long & Foster Real Estate, Inc., Lori R Gough
      Sold by Benson & Mangold, LLC, Brian Gearhart

      Use previous and next buttons to navigate

      103 Maple Ave, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      103 Maple Ave  Chestertown, MD 21620

      $615,000
      • Single Family
      • Closed
      • MLS # MDKE2006676
      • Updated 11 days ago
      • 4
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 6,434
        Sq. Ft.
      Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill
      Sold by Cross Street Realtors LLC, Richard Keaveney

      Use previous and next buttons to navigate

      107 Conley Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      3D Tour

      107 Conley Dr  Chestertown, MD 21620

      $245,000
      • Townhouse
      • Closed
      • MLS # MDKE2006828
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,140
        Sq. Ft.
      Listed by Benson & Mangold, LLC, Taylor Leaverton
      Sold by Cummings & Co. Realtors, Thomas W Chroniger Jr.

      Use previous and next buttons to navigate

      517 Round Top Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      517 Round Top Rd  Chestertown, MD 21620

      $289,000
      • Single Family
      • Closed
      • MLS # MDQA2017680
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,248
        Sq. Ft.
      Listed by Keller Williams Flagship, Barry Hess
      Sold by Coldwell Banker Chesapeake Real Estate Company, Lisa P Raffetto

      Use previous and next buttons to navigate

      110 Prospect St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      110 Prospect St  Chestertown, MD 21620

      $55,000
      • Single Family
      • Closed
      • MLS # MDKE2006626
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 2,210
        Sq. Ft.
      Listed by ANR Realty, LLC, Ana Lucia Ron
      Sold by Samson Properties, Alfonso Flores

      Use previous and next buttons to navigate

      7903 Radcliffe Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      7903 Radcliffe Rd  Chestertown, MD 21620

      $705,000
      • Single Family
      • Closed
      • MLS # MDKE2006890
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Partial Baths
      • 4
        Total Baths
      • 4,037
        Sq. Ft.
      • 2
        Car Garage
      Listed by Chesapeake Real Estate Associates, LLC, Erin Anderson
      Sold by Unrepresented, Unrepresented

      Use previous and next buttons to navigate

      22481 Goose Hollow Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      22481 Goose Hollow Dr  Chestertown, MD 21620

      $335,320
      • Single Family
      • Closed
      • MLS # MDKE2006682
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,296
        Sq. Ft.
      • 2
        Car Garage
      Listed by Keller Williams Legacy, Tom Atwood and Keller Williams Legacy, Phillip M Atwood
      Sold by Samson Properties, Tiffany Ann Ogden

      Use previous and next buttons to navigate

      107 Flying Cloud Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      107 Flying Cloud Dr  Chestertown, MD 21620

      $380,000
      • Single Family
      • Closed
      • MLS # MDKE2006510
      • 5
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,534
        Sq. Ft.
      Listed by CENTURY 21 New Millennium, Cynthia F Gardner
      Sold by RE/MAX Advantage Realty, Sharon Fisher

      Use previous and next buttons to navigate

      Preston Ln, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      Preston Ln  Chestertown, MD 21620

      $525,000
      • Single Family
      • Closed
      • MLS # MDKE2006820
      • 3
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 3,558
        Sq. Ft.
      • 2
        Car Garage
      Listed by Shoreline Realty, Robert G Shannahan
      Sold by Doug Ashley Realtors, LLC, Andrew Hanson Meikle

      Use previous and next buttons to navigate

      25440 Learman Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      25440 Learman Rd  Chestertown, MD 21620

      $3,000,000
      • Single Family
      • Closed
      • MLS # MDKE2006468
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Partial Baths
      • 4
        Total Baths
      • 3,142
        Sq. Ft.
      • 4
        Car Garage
      Listed by TTR Sotheby's International Realty, Liddy Campbell
      Sold by Martha Janney

      Use previous and next buttons to navigate

      109 Cedar St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      109 Cedar St  Chestertown, MD 21620

      $318,000
      • Single Family
      • Closed
      • MLS # MDKE2006792
      • 3
        Beds
      • 1
        Full Bath
      • 2
        Partial Baths
      • 3
        Total Baths
      • 1,397
        Sq. Ft.
      • 1
        Car Garage
      Listed by TTR Sotheby's International Realty, Liddy Campbell
      Sold by Chesapeake Real Estate Associates, LLC, Amy L Larrauri

      Use previous and next buttons to navigate

      202 Royston Shores Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      202 Royston Shores Rd  Chestertown, MD 21620

      $1,200,000
      • Single Family
      • Closed
      • MLS # MDQA2017462
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 2,292
        Sq. Ft.
      • 1
        Car Garage
      Listed by Cross Street Realtors LLC, Jody Baker
      Sold by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

      Use previous and next buttons to navigate

      102 Flying Cloud Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      102 Flying Cloud Dr  Chestertown, MD 21620

      $324,000
      • Single Family
      • Closed
      • MLS # MDKE2006586
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,896
        Sq. Ft.
      Listed by Long & Foster Real Estate, Inc., Daniel B Foster
      Sold by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland

      Use previous and next buttons to navigate

      311 Devon Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      311 Devon Dr  Chestertown, MD 21620

      $465,000
      • Single Family
      • Closed
      • MLS # MDKE2005930
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 5,342
        Sq. Ft.
      • 2
        Car Garage
      Listed by Doug Ashley Realtors, LLC, Debra B Meikle
      Sold by Cross Street Realtors LLC, Sarah E. King

      Use previous and next buttons to navigate

      7989 Quaker Neck Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      3D Tour

      7989 Quaker Neck Rd  Chestertown, MD 21620

      $1,900,000
      • Single Family
      • Closed
      • MLS # MDKE2005590
      • 5
        Beds
      • 4
        Full Baths
      • 1
        Partial Bath
      • 5
        Total Baths
      • 4,305
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Peter D Heller
      Sold by Long & Foster Real Estate, Inc., Kara Chaffin Donofrio

      Use previous and next buttons to navigate

      1904 Pondtown Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      1904 Pondtown Rd  Chestertown, MD 21620

      $247,500
      • Single Family
      • Closed
      • MLS # MDQA2017480
      • Updated 2 days ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,967
        Sq. Ft.
      Listed by Keller Williams Flagship, Alonzo Ellwood Gilmore
      Sold by Chesapeake Real Estate Associates, LLC, James M. Cronin

      Use previous and next buttons to navigate

      304 Hadaway Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      3D Tour

      304 Hadaway Dr  Chestertown, MD 21620

      $300,000
      • Single Family
      • Closed
      • MLS # MDKE2006482
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,325
        Sq. Ft.
      Listed by Redfin Corporation, Dawn W. Kane
      Sold by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair

      Use previous and next buttons to navigate

      7844 Chester Ct, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      7844 Chester Ct  Chestertown, MD 21620

      $640,000
      • Single Family
      • Closed
      • MLS # MDKE2005796
      • 4
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 3,248
        Sq. Ft.
      • 2
        Car Garage
      Listed by Doug Ashley Realtors, LLC, Retha J Arrabal
      Sold by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland

      Use previous and next buttons to navigate

      21217 Texas Ave, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      21217 Texas Ave  Chestertown, MD 21620

      $244,000
      • Single Family
      • Closed
      • MLS # MDKE2006364
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 912
        Sq. Ft.
      Listed by RE/MAX Leading Edge, Terry L Catalano
      Sold by Cross Street Realtors LLC, Sarah E. King

      Use previous and next buttons to navigate

      521 N Kent St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      521 N Kent St  Chestertown, MD 21620

      $365,000
      • Single Family
      • Closed
      • MLS # MDKE2006784
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 3,587
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Joseph S. Ciganek
      Sold by TTR Sotheby's International Realty, Liddy Campbell

      Use previous and next buttons to navigate

      100 Prospect St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      100 Prospect St  Chestertown, MD 21620

      $215,000
      • Single Family
      • Closed
      • MLS # MDKE2006544
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,373
        Sq. Ft.
      Listed by Real Broker, LLC - Chester, David J. Moore
      Sold by Bayside Realty, Dale C. Hunter, Jr.

      Find Recently Sold Homes in ZIP Code 21620

      Coldwell Banker Realty can help you find 21620 recently sold homes. Refine your 21620 recent sales search results by price, property type, bedrooms, baths and other features. Need more information? View our Chestertown real estate offices and let us help you find recent sales you're looking for.

      School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

      Assurant Home Warranty logo

      Protect your home and budget from life’s surprises with an Assurant Home Warranty, backed by a partner that supports you through every step of homeownership. Explore Plans

      Coldwell Banker Realty and Guaranteed Rate Affinity, LLC share common ownership and because of this relationship the brokerage may receive a financial or other benefit. You are not required to use Guaranteed Rate Affinity, LLC as a condition of purchase or sale of any real estate. Operating in the state of New York as GR Affinity, LLC in lieu of the legal name Guaranteed Rate Affinity, LLC.

      Real estate agents affiliated with Coldwell Banker are independent contractor sales associates and are not employees of Coldwell Banker.

      © 2026 Coldwell Banker. All Rights Reserved. Coldwell Banker and the Coldwell Banker logos are trademarks of Coldwell Banker Real Estate LLC. The Coldwell Banker® System is comprised of company owned offices which are owned by a subsidiary of Anywhere Advisors LLC and franchised offices which are independently owned and operated. The Coldwell Banker System fully supports the principles of the Fair Housing Act and the Equal Opportunity Act.

      Search options

      We can’t map any of the properties in your results.