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 109 Metcalf Road Chestertown, MD MLS# MDKE2005968
    • New Construction
    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
    The time to sell is now! THE TIME TO SELL IS NOW!
    View Cloquet Road Chestertown, MD MLS# MDKE2005966
    • 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 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 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 318 Lincoln Chestertown, MD MLS# MDKE2005842
    $269,000
    3

    Beds

    2.0

    Baths

    960

    Sq.Ft.

    318 Lincoln

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View Clarissa Road Chestertown, MD MLS# MDKE2005786
    $10,000
    Studio

    Beds

    0.0

    Baths

    Clarissa Road

    Chestertown, MD

    Bright
    Courtesy of SAMSON PROPERTIES
    View 107 Malone Avenue Chestertown, MD MLS# MDKE2005764
    $290,000
    3

    Beds

    1.0

    Baths

    1,200

    Sq.Ft.

    107 Malone Avenue

    Chestertown, MD

    Bright
    Courtesy of DOUGLAS REALTY LLC
    View 423 Calvert Street Chestertown, MD MLS# MDKE2005718
    $135,000
    3

    Beds

    1.1

    Baths

    1,136

    Sq.Ft.

    423 Calvert Street

    Chestertown, MD

    Bright
    Courtesy of REDFIN CORP
    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 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 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 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 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 Sandpiper Road Chestertown, MD MLS# MDKE2005542
    $9,000
    Studio

    Beds

    0.0

    Baths

    Sandpiper Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 112 Metcalf Road Chestertown, MD MLS# MDKE2005498
    $249,950
    3

    Beds

    1.1

    Baths

    1,280

    Sq.Ft.

    112 Metcalf Road

    Chestertown, MD

    Bright
    Courtesy of ENGEL & VOLKERS ANNAPOLIS

    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

    106

    Estimated median home price

    $333,950
    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 - 100K33
    $100K - 200K7
    $200K - 300K10
    $300K - 400K16
    $400K - 500K7
    $500K - 600K5
    $600K - 700K6
    $700K - 800K6
    $800K - 900K5
    $900K - 1M0
    $1M - Max11

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family39
    Townhouse8
    Condo12
    Commercial4
    Rental5
    Lots and Land41
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms1

    (Data as of 1/2/2026)

    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.

    © 2026 BrightMLS. All Rights Reserved.