Recently Viewed Properties
99 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
      99 Results
      Order By

      Use previous and next buttons to navigate

      118 Little Harbor Way, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      118 Little Harbor Way  #202  Chestertown, MD 21620

      $660,000
      • Condo
      • Closed
      • MLS # MDKE2005800
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,600
        Sq. Ft.
      • 1
        Car Garage
      Listed by Benson & Mangold, LLC, Kaitlyn Cole Collins
      Sold by Doug Ashley Realtors, LLC, Douglas J Ashley

      Use previous and next buttons to navigate

      115 Acorn Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      115 Acorn Dr  Chestertown, MD 21620

      $290,000
      • Townhouse
      • Closed
      • MLS # MDKE2006360
      • 2
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,864
        Sq. Ft.
      • 1
        Car Garage
      Listed by Chesapeake Real Estate Associates, LLC, Amy L Larrauri
      Sold by Doug Ashley Realtors, LLC, Vincenzo Assante Di Cupillo

      Use previous and next buttons to navigate

      22360 Great Oak Landing Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      22360 Great Oak Landing Rd  Chestertown, MD 21620

      $525,000
      • Single Family
      • Closed
      • MLS # MDKE2006478
      • 5
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 2,688
        Sq. Ft.
      • 2
        Car Garage
      Listed by Doug Ashley Realtors, LLC, Michele A Palmer
      Sold by Compass Realty, Inc., Michele Gilden

      Use previous and next buttons to navigate

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

      1/1

      201 Birch Run Rd  Chestertown, MD 21620

      $430,000
      • Single Family
      • Closed
      • MLS # MDKE2006316
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,588
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill
      Sold by Blackwell Real Estate, LLC, Christina Cartagirone

      Use previous and next buttons to navigate

      2032 Pondtown Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      2032 Pondtown Rd  Chestertown, MD 21620

      $365,000
      • Single Family
      • Closed
      • MLS # MDQA2016688
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,120
        Sq. Ft.
      Listed by Northrop Realty, Joie L White
      Sold by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland

      Use previous and next buttons to navigate

      10594 Millbrook Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      10594 Millbrook Dr  Chestertown, MD 21620

      $329,000
      • Single Family
      • Closed
      • MLS # MDKE2006378
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,499
        Sq. Ft.
      Listed by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair
      Sold by Unrepresented, Unrepresented

      Use previous and next buttons to navigate

      154 Longfellow Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      154 Longfellow Dr  Chestertown, MD 21620

      $300,000
      • Single Family
      • Closed
      • MLS # MDQA2016250
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 2,112
        Sq. Ft.
      Listed by Cross Street Realtors LLC, Kaitlin Grace Stecklair
      Sold by CR Realty, Candice Santoro

      Use previous and next buttons to navigate

      25475 Turnberry Ct, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      25475 Turnberry Ct  Chestertown, MD 21620

      $825,000
      • Single Family
      • Closed
      • MLS # MDKE2006350
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 5,290
        Sq. Ft.
      • 5
        Car Garage
      Listed by Taylor Properties, Lona Sue Todd
      Sold by Unrepresented, Unrepresented

      Use previous and next buttons to navigate

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

      1/1

      109 Metcalf Rd  Chestertown, MD 21620

      $264,900
      • Townhouse
      • Closed
      • MLS # MDKE2005968
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,280
        Sq. Ft.
      Listed by Real Broker, LLC, David J. Moore
      Sold by Real Broker, LLC, WALLACE G BOOTH Jr.

      Use previous and next buttons to navigate

      349 & 351 High St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      349 & 351 High St  Chestertown, MD 21620

      $355,000
      • Townhouse
      • Closed
      • MLS # MDKE2003720
      • 3,664
        Sq. Ft.
      Listed by Coldwell Banker Chesapeake Real Estate Company, Cheryl Hurt
      Sold by Taylor Properties, Julie H SANTOBONI

      Use previous and next buttons to navigate

      108 Oak Leaf Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      108 Oak Leaf Dr  Chestertown, MD 21620

      $296,500
      • Townhouse
      • Closed
      • MLS # MDKE2006224
      • 2
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,867
        Sq. Ft.
      • 1
        Car Garage
      Listed by Doug Ashley Realtors, LLC, Grace M Crockett
      Sold by Chesapeake Real Estate Associates, LLC, Maryn J. LeClair

      Use previous and next buttons to navigate

      136 Hilltop Dr, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      3D Tour

      136 Hilltop Dr  Chestertown, MD 21620

      $376,000
      • Single Family
      • Closed
      • MLS # MDQA2016782
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,432
        Sq. Ft.
      • 1
        Car Garage
      Listed by Northrop Realty, Joie L White
      Sold by Long & Foster Real Estate, Inc., Warren S Hogan

      Use previous and next buttons to navigate

      10087 John Carvill Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      10087 John Carvill Rd  Chestertown, MD 21620

      $695,000
      • Single Family
      • Closed
      • MLS # MDKE2006324
      • 3
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,566
        Sq. Ft.
      Listed by Coldwell Banker Chesapeake Real Estate Company, Jennifer L Mobley
      Sold by RE/MAX Chesapeake, Donnie M Horton

      Use previous and next buttons to navigate

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

      1/1

      107 Metcalf Rd  Chestertown, MD 21620

      $259,900
      • Townhouse
      • Closed
      • MLS # MDKE2006186
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,200
        Sq. Ft.
      Listed by Real Broker, LLC, David J. Moore
      Sold by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

      Use previous and next buttons to navigate

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

      1/1

      107 Conley Dr  Chestertown, MD 21620

      $150,000
      • Townhouse
      • Closed
      • MLS # MDKE2006220
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 1,140
        Sq. Ft.
      Listed by Doug Ashley Realtors, LLC, Debra B Meikle
      Sold by Benson & Mangold, LLC, Taylor Leaverton

      Use previous and next buttons to navigate

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

      1/1

      107 Longfellow Dr  Chestertown, MD 21620

      $278,500
      • Single Family
      • Closed
      • MLS # MDQA2016720
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 3
        Car Garage
      Listed by Doug Ashley Realtors, LLC, Douglas J Ashley
      Sold by Lofgren-Sargent Real Estate, Arian Sargent Lucas

      Use previous and next buttons to navigate

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

      1/1

      132 Prospect St  Chestertown, MD 21620

      $155,000
      • Single Family
      • Closed
      • MLS # MDKE2006110
      • 2
        Beds
      • 1
        Full Bath
      • 1
        Total Bath
      • 910
        Sq. Ft.
      Listed by ANR Realty, LLC, Ana Lucia Ron
      Sold by Long & Foster Real Estate, Inc., Ashley Monico

      Use previous and next buttons to navigate

      100 Adela Way, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      100 Adela Way  Chestertown, MD 21620

      $490,000
      • Single Family
      • Closed
      • MLS # MDKE2005636
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 4,499
        Sq. Ft.
      • 2
        Car Garage
      Listed by Berkshire Hathaway HomeServices PenFed Realty, Lauren Matera and Berkshire Hathaway HomeServices PenFed Realty, Alyssa Smith
      Sold by Keller Williams Gateway LLC, Dawn M Jones

      Use previous and next buttons to navigate

      101 Pine Tree Rd, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      101 Pine Tree Rd  Chestertown, MD 21620

      $480,000
      • Single Family
      • Closed
      • MLS # MDQA2016188
      • 4
        Beds
      • 2
        Full Baths
      • 2
        Total Baths
      • 1,848
        Sq. Ft.
      • 2
        Car Garage
      Listed by Rosendale Realty, Michael Rosendale and Rosendale Realty, Megan E Rosendale
      Sold by RE/MAX Executive, Megan Travers

      Use previous and next buttons to navigate

      217 Philosophers Terrace, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      217 Philosophers Terrace  Chestertown, MD 21620

      $370,000
      • Single Family
      • Closed
      • MLS # MDKE2006332
      • 3
        Beds
      • 1
        Full Bath
      • 1
        Partial Bath
      • 2
        Total Baths
      • 1,404
        Sq. Ft.
      • 1
        Car Garage
      Listed by TTR Sotheby's International Realty, Courtney Chipouras
      Sold by Cross Street Realtors LLC, Sarah E. King

      Use previous and next buttons to navigate

      206 S Water St, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      206 S Water St  Chestertown, MD 21620

      $545,000
      • Single Family
      • Closed
      • MLS # MDKE2006058
      • 4
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,008
        Sq. Ft.
      Listed by TTR Sotheby's International Realty, Thomas C Williams Jr.
      Sold by Coldwell Banker Chesapeake Real Estate Company, Michael ONeill

      Use previous and next buttons to navigate

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

      1/1

      103 Flying Cloud Dr  Chestertown, MD 21620

      $339,900
      • Single Family
      • Closed
      • MLS # MDKE2006154
      • 3
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 1,724
        Sq. Ft.
      Listed by American Premier Realty, LLC, Laura M Snyder
      Sold by American Premier Realty, LLC, Priscilla J Anderson

      Use previous and next buttons to navigate

      11040 Kylie Ln, Chestertown, MD 21620 - Photo 1
      Sold

      1/1

      11040 Kylie Ln  Chestertown, MD 21620

      $620,000
      • Single Family
      • Closed
      • MLS # MDKE2004586
      • 4
        Beds
      • 3
        Full Baths
      • 1
        Partial Bath
      • 4
        Total Baths
      • 3,884
        Sq. Ft.
      • 2
        Car Garage
      Listed by Coldwell Banker Chesapeake Real Estate Company, Kristina L Hyland
      Sold by LPT Realty, LLC, Jordan Evan Larigan

      Use previous and next buttons to navigate

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

      1/1

      515 N Kent St  Chestertown, MD 21620

      $495,000
      • Single Family
      • Closed
      • MLS # MDKE2006204
      • 4
        Beds
      • 2
        Full Baths
      • 1
        Partial Bath
      • 3
        Total Baths
      • 2,220
        Sq. Ft.
      • 1
        Car Garage
      Listed by Cross Street Realtors LLC, Jody Baker
      Sold by Benson & Mangold, LLC, Connor LeMire

      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.

      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.