Recently Viewed Properties
92 Results

Chestertown, MD 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
      92 Results
      Order By

      Use previous and next buttons to navigate

      10230 John Carvill Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      10230 John Carvill Rd  Chestertown, MD 21620

      $740,000
      • Single Family
      • Closed
      • MLS # MDKE2005716
      • Updated 4 hours ago
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 2,350
        Sq. Ft.
      Listed by Shoreline Realty, Robert G Shannahan
      Sold by Cross Street Realtors LLC, Richard Keaveney

      Use previous and next buttons to navigate

      206 Valley, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      206 Valley  Chestertown, MD 21620

      $590,000
      • Single Family
      • Closed
      • MLS # MDKE2005762
      • Updated 3 days ago
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 3,981
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Peter D Heller
      Sold by Doug Ashley Realtors, LLC, Grace M Crockett

      Use previous and next buttons to navigate

      26933 Mallard Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      26933 Mallard Rd  Chestertown, MD 21620

      $555,000
      • Single Family
      • Closed
      • MLS # MDKE2005422
      • Updated 3 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,600
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Peter D Heller and Coldwell Banker Chesapeake Real Estate Company, Joan O Horsey
      Sold by Coldwell Banker Chesapeake Real Estate Company, Joseph S. Ciganek

      Use previous and next buttons to navigate

      7653 Broad Neck Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      7653 Broad Neck Rd  Chestertown, MD 21620

      $375,000
      • Single Family
      • Closed
      • MLS # MDKE2005742
      • Updated 6 days ago
      • 4
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 1,790
        Sq. Ft.
      • 2
        Car Garage
      Listed by Benson & Mangold, LLC, Brian R Petzold
      Sold by Pearson Smith Realty, LLC, Boyd Grainger

      Use previous and next buttons to navigate

      411 Greenwood Ave, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      411 Greenwood Ave  Chestertown, MD 21620

      $415,000
      • Single Family
      • Closed
      • MLS # MDKE2005824
      • Updated 8 days ago
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,676
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Mary C Carlisle
      Sold by Monument Sotheby's International Realty, Rachael Altemose

      Use previous and next buttons to navigate

      5700 Johnsontown Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      5700 Johnsontown Rd  Chestertown, MD 21620

      $80,000
      • Single Family
      • Closed
      • MLS # MDKE2005562
      • Updated 13 days ago
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,144
        Sq. Ft.
      Listed by Tesla Realty Group, LLC, Nicole Stephens
      Sold by Coldwell Banker Chesapeake Real Estate Company, Jyaire T McCall

      Use previous and next buttons to navigate

      492 Pear Tree Point Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      492 Pear Tree Point Rd  Chestertown, MD 21620

      $850,000
      • Single Family
      • Closed
      • MLS # MDQA2015126
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 4,770
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Joseph S. Ciganek
      Sold by Benson & Mangold, LLC, Brian K Gearhart

      Use previous and next buttons to navigate

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

      1/1

      517 High St  Chestertown, MD 21620

      $361,500
      • Single Family
      • Closed
      • MLS # MDKE2005736
      • 1,728
        Sq. Ft.
      Listed by L. C. Parker Real Estate, Kristie R Midash
      Sold by Select Land & Homes, LLC, Hayley A Norris

      Use previous and next buttons to navigate

      25195 Lovers Ln, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      25195 Lovers Ln  Chestertown, MD 21620

      $350,000
      • Single Family
      • Closed
      • MLS # MDKE2005986
      • 1
        Bed
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,002
        Sq. Ft.
      Listed by Select Land & Homes, LLC, William H Norris III and Select Land & Homes, LLC, Hayley A Norris
      Sold by Unrepresented Buyer Office, Unrepresented Buyer

      Use previous and next buttons to navigate

      101 Birch Run Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      101 Birch Run Rd  Chestertown, MD 21620

      $475,000
      • Single Family
      • Closed
      • MLS # MDKE2005810
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,961
        Sq. Ft.
      • 2
        Car Garage
      Listed by Remax Vision, Julie A. Strickler
      Sold by RE/MAX Real Estate Connections, Shelley A Mastro

      Use previous and next buttons to navigate

      23393 Cacaway Farm Ln, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      23393 Cacaway Farm Ln  Chestertown, MD 21620

      $1,150,000
      • Condo
      • Closed
      • MLS # MDKE2004002
      • 3
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 6,361
        Sq. Ft.
      • 2
        Car Garage
      Listed by Gunther-McClary Real Estate, Ashton M Kelley
      Sold by Rock Hall Properties Real Estate, Sarah A Ulrick

      Use previous and next buttons to navigate

      101 Metcalf Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      101 Metcalf Rd  Chestertown, MD 21620

      $264,900
      • Townhouse
      • Closed
      • MLS # MDKE2005882
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,280
        Sq. Ft.
      Listed by Real Broker, LLC, David J. J Moore
      Sold by Chesapeake Real Estate Associates, LLC, Erin Anderson

      Use previous and next buttons to navigate

      302 Rosin Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      302 Rosin Dr  Chestertown, MD 21620

      $550,000
      • Single Family
      • Closed
      • MLS # MDQA2015470
      • 5
        Beds
      • 4
        Full Baths
      • 4
        Total Baths
      • 4,157
        Sq. Ft.
      • 1
        Car Garage
      Listed by Cross Street Realtors LLC, Lori A. Willis
      Sold by Cross Street Realtors LLC, Jody Baker

      Use previous and next buttons to navigate

      600 Rosin Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      600 Rosin Dr  Chestertown, MD 21620

      $413,300
      • Single Family
      • Closed
      • MLS # MDQA2014896
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,300
        Sq. Ft.
      Listed by Doug Ashley Realtors, LLC, Michele A Palmer
      Sold by Doug Ashley Realtors, LLC, Andrew Hanson Meikle

      Use previous and next buttons to navigate

      7483 Shortall St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      7483 Shortall St  Chestertown, MD 21620

      $287,500
      • Single Family
      • Closed
      • MLS # MDKE2005616
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,232
        Sq. Ft.
      Listed by RE/MAX Executive, Christine Johnson
      Sold by ExecuHome Realty, Rose Marie Calderone

      Use previous and next buttons to navigate

      8951 Orchard Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      8951 Orchard Dr  Chestertown, MD 21620

      $700,000
      • Single Family
      • Closed
      • MLS # MDKE2005836
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 3,735
        Sq. Ft.
      • 2
        Car Garage
      Listed by Rock Hall Properties Real Estate, Sarah A Ulrick and Rock Hall Properties Real Estate, Cindy Genther
      Sold by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland

      Use previous and next buttons to navigate

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

      1/1

      119 High St  Chestertown, MD 21620

      $1,165,000
      • Single Family
      • Closed
      • MLS # MDKE2005728
      • 5
        Beds
      • 4
        Full Baths
      • 1
        Partial Bath
      • 5
        Total Baths
      • 5,345
        Sq. Ft.
      • 1
        Car Garage
      Listed by Cross Street Realtors LLC, Richard Keaveney
      Sold by Cross Street Realtors LLC, Casey Scattergood

      Use previous and next buttons to navigate

      907 N Meadowview Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      907 N Meadowview Dr  Chestertown, MD 21620

      $375,000
      • Single Family
      • Closed
      • MLS # MDKE2005540
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,842
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, William Sutton and Coldwell Banker Chesapeake Real Estate Company, Lacey R Sutton
      Sold by Cross Street Realtors LLC, Sarah E. King

      Use previous and next buttons to navigate

      212 Landing Ln, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      212 Landing Ln  Chestertown, MD 21620

      $750,000
      • Townhouse
      • Closed
      • MLS # MDKE2004782
      • 3
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      Listed by Gunther-McClary Real Estate, John J Burke and Gunther-McClary Real Estate, Julia Hilfiker
      Sold by Unrepresented Buyer Office, Unrepresented Buyer

      Use previous and next buttons to navigate

      221 Old Bridge Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      221 Old Bridge Rd  Chestertown, MD 21620

      $359,900
      • Single Family
      • Closed
      • MLS # MDQA2014888
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 2,527
        Sq. Ft.
      Listed by TTR Sotheby's International Realty, Courtney Chipouras
      Sold by Coldwell Banker Chesapeake Real Estate Company, Terri L Kulp

      Use previous and next buttons to navigate

      23620 Land's End Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      23620 Land's End Rd  Chestertown, MD 21620

      $4,221,800
      • Single Family
      • Closed
      • MLS # MDKE2004760
      • 5
        Beds
      • 6
        Full Baths
      • 2
        Partial Baths
      • 8
        Total Baths
      • 12,574
        Sq. Ft.
      • 2
        Car Garage
      Listed by Cross Street Realtors LLC, Richard Keaveney
      Sold by Cross Street Realtors LLC, Casey Scattergood and Cross Street Realtors LLC, John Boniface

      Use previous and next buttons to navigate

      10761 Kasota Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      10761 Kasota Rd  Chestertown, MD 21620

      $872,500
      • Single Family
      • Closed
      • MLS # MDKE2005698
      • 3
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 2,582
        Sq. Ft.
      Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill
      Sold by Compass, Daniel Brewer

      Use previous and next buttons to navigate

      126 Metcalf Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      126 Metcalf Rd  Chestertown, MD 21620

      $230,000
      • Single Family
      • Closed
      • MLS # MDKE2005734
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,140
        Sq. Ft.
      Listed by Taylor Properties, Brenda K Fornos
      Sold by Benson & Mangold, LLC., Kathleen A Thompson

      Use previous and next buttons to navigate

      201 Boundary Ave, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      201 Boundary Ave  Chestertown, MD 21620

      $425,000
      • Single Family
      • Closed
      • MLS # MDQA2014272
      • 3
        Beds
      • 3
        Full Baths
      • 3
        Total Baths
      • 3,096
        Sq. Ft.
      Listed by Coldwell Banker Chesapeake Real Estate Company, Mary C Carlisle
      Sold by Cross Street Realtors LLC, John Boniface

      Find Recently Sold Homes in Chestertown, MD

      Coldwell Banker Realty can help you find Chestertown recently sold homes. Refine your Chestertown 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.

      Cities Near Chestertown, MD

      ZIP Codes Near Chestertown, MD

      Offices serving Chestertown, MD

      Boundaries © 2014-2018 Pitney Bowes Inc. All rights reserved. School attendance zone boundaries are subject to change. Check with the applicable school district prior to making a decision based on these results.

      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.