View 423 Calvert Street Chestertown, MD MLS# MDKE2005718
$165,000
3

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

Bright
Courtesy of REDFIN CORP
View 7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742
$375,000
4

Beds

3.0

Baths

1,790

Sq.Ft.

7653 Broad Neck Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 517 High Street Chestertown, MD MLS# MDKE2005736
$389,900
3

Beds

0.0

Baths

517 High Street

Chestertown, MD

Bright
Courtesy of L. C. PARKER REAL ESTATE
The time to sell is now! THE TIME TO SELL IS NOW!
View 100 Adela Way Chestertown, MD MLS# MDKE2005636
  • Virtual Tour
1 of 71
$515,000
4

Beds

3.1

Baths

3,799

Sq.Ft.

100 Adela Way

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 103 Metcalf Rd Chestertown, MD MLS# MDKE2005688
  • New Construction
1 of 25
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 23110 Old Fairlee Road Chestertown, MD MLS# MDKE2005676
$359,900
3

Beds

1.0

Baths

1,805

Sq.Ft.

23110 Old Fairlee Road

Chestertown, MD

Bright
Courtesy of REAL BROKER LLC
View 103 Landing Lane Chestertown, MD MLS# MDKE2005670
    1 of 69
    OPEN HOUSE: Saturday 12/6 10:00 AM - 1:00 PM
    $539,999
    2

    Beds

    2.1

    Baths

    2,100

    Sq.Ft.

    103 Landing Lane

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 21316 Persimmon Drive Chestertown, MD MLS# MDKE2005624
    $179,000
    2

    Beds

    1.0

    Baths

    1,232

    Sq.Ft.

    21316 Persimmon Drive

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    View 10751 Millbrook Drive Chestertown, MD MLS# MDKE2005652
    $350,000
    3

    Beds

    2.0

    Baths

    1,942

    Sq.Ft.

    10751 Millbrook Drive

    Chestertown, MD

    Bright
    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    View 23043 Bay Shore Spur Chestertown, MD MLS# MDKE2005584
    $325,000
    4

    Beds

    3.0

    Baths

    2,630

    Sq.Ft.

    23043 Bay Shore Spur

    Chestertown, MD

    Bright
    Courtesy of ROCK HALL PROPERTIES REAL ESTATE
    View 100 Metcalf Road Chestertown, MD MLS# MDKE2005634
    $245,000
    3

    Beds

    2.0

    Baths

    1,140

    Sq.Ft.

    100 Metcalf Road

    Chestertown, MD

    Bright
    Courtesy of BAYSIDE REALTY
    View 7989 Quaker Neck Road Chestertown, MD MLS# MDKE2005590
    $2,500,000
    5

    Beds

    4.1

    Baths

    4,305

    Sq.Ft.

    7989 Quaker Neck Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 7483 Shortall Street Chestertown, MD MLS# MDKE2005616
    $290,000
    3

    Beds

    2.0

    Baths

    1,232

    Sq.Ft.

    7483 Shortall Street

    Chestertown, MD

    Bright
    Courtesy of RE/MAX EXECUTIVE
    View 116 Harlan Loop Chestertown, MD MLS# MDKE2005610
    $519,000
    5

    Beds

    3.1

    Baths

    4,067

    Sq.Ft.

    116 Harlan Loop

    Chestertown, MD

    Bright
    Courtesy of SAMSON PROPERTIES
    View Buck Neck Landing Road Chestertown, MD MLS# MDKE2005586
    $10,000
    Studio

    Beds

    0.0

    Baths

    Buck Neck Landing Road

    Chestertown, MD

    Bright
    Courtesy of ROSENDALE REALTY
    View Tonopah Rd. Chestertown, MD MLS# MDKE2005564
    $40,000
    Studio

    Beds

    0.0

    Baths

    Tonopah Rd.

    Chestertown, MD

    Bright
    Courtesy of THE HOGANS AGENCY
    View 5700 Johnsontown Road Chestertown, MD MLS# MDKE2005562
    $110,000
    3

    Beds

    1.0

    Baths

    1,144

    Sq.Ft.

    5700 Johnsontown Road

    Chestertown, MD

    Bright
    Courtesy of TESLA REALTY GROUP, LLC
    View 200 Washington Avenue Chestertown, MD MLS# MDKE2005538
      1 of 35
      OPEN HOUSE: Saturday 12/6 11:00 AM - 1:00 PM
      $695,000
      4

      Beds

      3.1

      Baths

      2,917

      Sq.Ft.

      200 Washington Avenue

      Chestertown, MD

      Bright
      Courtesy of CROSS STREET REALTORS LLC
      View Johnsontown Road Chestertown, MD MLS# MDKE2005550
      $35,000
      Studio

      Beds

      0.0

      Baths

      Johnsontown Road

      Chestertown, MD

      Bright
      Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
      View 251 Devon Drive Chestertown, MD MLS# MDKE2005536
      $595,000
      3

      Beds

      2.1

      Baths

      3,935

      Sq.Ft.

      251 Devon Drive

      Chestertown, MD

      Bright
      Courtesy of DOUG ASHLEY REALTORS, LLC

      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

      120

      Estimated median home price

      $320,000
      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 - 100K37
      $100K - 200K10
      $200K - 300K11
      $300K - 400K14
      $400K - 500K11
      $500K - 600K5
      $600K - 700K8
      $700K - 800K4
      $800K - 900K6
      $900K - 1M0
      $1M - Max14

      Homes for Sale by Type in Chestertown, MD

      Property TypeCount
      Single Family49
      Townhouse9
      Condo9
      Commercial6
      Rental4
      Lots and Land44
      Condo/Town/CoOp0
      CoOp0
      Multi Family2
      Mobile Home0
      Farms1

      (Data as of 11/11/2025)

      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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