View 24775 Langford Road Chestertown, MD MLS# MDKE2005992
    1 of 9
    OPEN HOUSE: Saturday 1/3 12:00 PM - 3:00 PM
    $319,900
    3

    Beds

    1.0

    Baths

    1,008

    Sq.Ft.

    24775 Langford Road

    Chestertown, MD

    Bright
    Courtesy of RE/MAX 1ST CHOICE - MIDDLETOWN
    View 23698 L Road Chestertown, MD MLS# MDKE2005988
    • Recently Listed
    1 of 5
    $29,000
    Studio

    Beds

    0.0

    Baths

    23698 L Road

    Chestertown, MD

    Bright
    Courtesy of TAYLOR PROPERTIES
    View 303 Cedar Street Chestertown, MD MLS# MDKE2005970
    $333,900
    3

    Beds

    2.1

    Baths

    2,577

    Sq.Ft.

    303 Cedar Street

    Chestertown, MD

    Bright
    Courtesy of SELECT LAND & HOMES, LLC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 109 Metcalf Road Chestertown, MD MLS# MDKE2005968
    • Recently Listed
    1 of 27
    $264,900
    3

    Beds

    1.1

    Baths

    1,280

    Sq.Ft.

    109 Metcalf Road

    Chestertown, MD

    Bright
    Courtesy of REAL BROKER, LLC
    View Cloquet Road Chestertown, MD MLS# MDKE2005966
    • Recently Listed with Virtual Tour
    1 of 32
    $39,000
    Studio

    Beds

    0.0

    Baths

    Cloquet Road

    Chestertown, MD

    Bright
    Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
    View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
      1 of 1
      OPEN HOUSE: Saturday 1/3 2:00 PM - 4:00 PM
      $475,000
      4

      Beds

      2.1

      Baths

      2,880

      Sq.Ft.

      110 Trafford Drive

      Chestertown, MD

      Bright
      Courtesy of RE/MAX ADVANTAGE REALTY
      View 102 Little Harbor Way Chestertown, MD MLS# MDKE2005950
      $839,500
      3

      Beds

      2.1

      Baths

      1,964

      Sq.Ft.

      102 Little Harbor Way

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 104 Landing Lane Chestertown, MD MLS# MDKE2005952
      • New Construction
      1 of 24
      $813,900
      3

      Beds

      3.1

      Baths

      2,192

      Sq.Ft.

      104 Landing Lane

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View #25 Landing Lane Chestertown, MD MLS# MDKE2005954
      • New Construction
      1 of 22
      $1,099,900
      4

      Beds

      3.1

      Baths

      2,784

      Sq.Ft.

      #25 Landing Lane

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View #35 Landing Lane Chestertown, MD MLS# MDKE2005956
      • New Construction
      1 of 26
      $786,900
      3

      Beds

      2.1

      Baths

      1,964

      Sq.Ft.

      #35 Landing Lane

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View #36 Landing Lane Chestertown, MD MLS# MDKE2005958
      • New Construction
      1 of 26
      $753,500
      3

      Beds

      2.1

      Baths

      1,964

      Sq.Ft.

      #36 Landing Lane

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View #37 Landing Lane Chestertown, MD MLS# MDKE2005960
      • New Construction
      1 of 24
      $765,900
      3

      Beds

      2.1

      Baths

      1,964

      Sq.Ft.

      #37 Landing Lane

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
      • Virtual Tour
      1 of 40
      OPEN HOUSE: Saturday 1/3 2:00 PM - 4:00 PM
      $598,000
      5

      Beds

      3.1

      Baths

      3,504

      Sq.Ft.

      311 Devon Drive

      Chestertown, MD

      Bright
      Courtesy of DOUG ASHLEY REALTORS, LLC
      View 21111 Texas Avenue Chestertown, MD MLS# MDKE2005932
      $370,000
      3

      Beds

      2.0

      Baths

      1,680

      Sq.Ft.

      21111 Texas Avenue

      Chestertown, MD

      Bright
      Courtesy of KELLER WILLIAMS SELECT REALTORS OF EASTON
      View 108 Flying Cloud Drive Chestertown, MD MLS# MDKE2005928
      $364,900
      4

      Beds

      2.1

      Baths

      1,936

      Sq.Ft.

      108 Flying Cloud Drive

      Chestertown, MD

      Bright
      Courtesy of CROSS STREET REALTORS LLC
      View Georgetown Road Chestertown, MD MLS# MDKE2005844
      $89,500
      Studio

      Beds

      0.0

      Baths

      Georgetown Road

      Chestertown, MD

      Bright
      Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
      View 7521 Pine Avenue Chestertown, MD MLS# MDKE2005920
      $250,000
      3

      Beds

      1.0

      Baths

      1,040

      Sq.Ft.

      7521 Pine Avenue

      Chestertown, MD

      Bright
      Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
      View 108 Little Harbor Way Chestertown, MD MLS# MDKE2005902
      $635,000
      Studio

      Beds

      0.0

      Baths

      108 Little Harbor Way

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE
      View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
      $299,000
      2

      Beds

      1.1

      Baths

      920

      Sq.Ft.

      611 Cannon Street

      Chestertown, MD

      Bright
      Courtesy of SELECT LAND & HOMES, LLC
      View Little Harbor Way # 1 Chestertown, MD MLS# MDKE2005768
      • New Construction with Virtual Tour
      1 of 25
      $1,459,000
      3

      Beds

      2.1

      Baths

      2,231

      Sq.Ft.

      Little Harbor Way # 1

      Chestertown, MD

      Bright
      Courtesy of GUNTHER-MCCLARY REAL ESTATE

      About Chestertown

      Home of George Washington College, Chestertown is the center of amenities and the hub of life in Kent County.  Located on the banks of the Chester River, Chestertown began as a prosperous shipbuilding, trade and government center during the colonial movement and still maintains the state’s oldest records.  The popular autumn Candlelight Walking Tour offers a glimpse into many of the spectacular homes built by wealthy merchants of the 18th and 19th centuries.  Quaint red-brick sidewalks and broad, shaded streets form an idyllic backdrop for specialty shops, galleries and eateries.  On cool summer evenings, residents can relax to the strains of concerts held around the antique fountain in the town square.  Lovely homes, a stimulating college-town atmosphere and community pride make Chestertown the ideal place to call home. 

      Listings in Chestertown, MD

      108

      Estimated median home price

      $329,450
      Chestertown MD Homes for Sale & Properties

      Weichert Realtors is one of the nation's leading providers of Chestertown, Maryland real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Chestertown, MD.

      Homes for Sale by Price in Chestertown, MD

      PriceCount
      $0 - 100K34
      $100K - 200K8
      $200K - 300K10
      $300K - 400K16
      $400K - 500K6
      $500K - 600K5
      $600K - 700K6
      $700K - 800K6
      $800K - 900K6
      $900K - 1M0
      $1M - Max11

      Homes for Sale by Type in Chestertown, MD

      Property TypeCount
      Single Family39
      Townhouse8
      Condo12
      Commercial5
      Rental5
      Lots and Land42
      Condo/Town/CoOp0
      CoOp0
      Multi Family1
      Mobile Home0
      Farms1

      (Data as of 12/29/2025)

      Information deemed reliable but not guaranteed.

      Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

      Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

      The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

      Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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