View 23055 Old Fairlee Road Chestertown, MD MLS# MDKE2006062
$330,000
3

Beds

2.0

Baths

1,628

Sq.Ft.

23055 Old Fairlee Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 24339 Chestertown Road Chestertown, MD MLS# MDKE2006054
$269,000
3

Beds

1.0

Baths

960

Sq.Ft.

24339 Chestertown Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 141 Prospect Street Chestertown, MD MLS# MDKE2006036
$165,000
4

Beds

1.1

Baths

1,156

Sq.Ft.

141 Prospect Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
View 22681 Wood Yard Lane Chestertown, MD MLS# MDKE2006032
$15,000
Studio

Beds

0.0

Baths

22681 Wood Yard Lane

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 22481 Goose Hollow Drive Chestertown, MD MLS# MDKE2006012
    1 of 18
    OPEN HOUSE: Sunday 1/25 1:00 PM - 3:00 PM
    $379,500
    3

    Beds

    2.0

    Baths

    1,296

    Sq.Ft.

    22481 Goose Hollow Drive

    Chestertown, MD

    Bright
    Courtesy of REALTY MARK CITYSCAPE
    View 24775 Langford Road Chestertown, MD MLS# MDKE2005992
    $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
    $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
    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
    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 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 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 204 Rolling Road Chestertown, MD MLS# MDKE2005896
    $345,000
    3

    Beds

    2.0

    Baths

    2,296

    Sq.Ft.

    204 Rolling Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 304 Hadaway Drive Chestertown, MD MLS# MDKE2005848
    $350,000
    4

    Beds

    2.0

    Baths

    1,325

    Sq.Ft.

    304 Hadaway Drive

    Chestertown, MD

    Bright
    Courtesy of CUMMINGS & CO. REALTORS
    View 8750 Georgetown Road Chestertown, MD MLS# MDKE2005834
    $334,000
    3

    Beds

    2.0

    Baths

    1,900

    Sq.Ft.

    8750 Georgetown Road

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View Clarissa Road Chestertown, MD MLS# MDKE2005786
    $10,000
    Studio

    Beds

    0.0

    Baths

    Clarissa Road

    Chestertown, MD

    Bright
    Courtesy of SAMSON PROPERTIES
    View 8833 Georgetown Road Chestertown, MD MLS# MDKE2005766
    $364,000
    4

    Beds

    2.0

    Baths

    1,625

    Sq.Ft.

    8833 Georgetown Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    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

    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

    104

    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 - 100K32
    $100K - 200K8
    $200K - 300K10
    $300K - 400K16
    $400K - 500K8
    $500K - 600K5
    $600K - 700K3
    $700K - 800K5
    $800K - 900K5
    $900K - 1M0
    $1M - Max12

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family39
    Townhouse7
    Condo11
    Commercial5
    Rental7
    Lots and Land40
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms1

    (Data as of 1/16/2026)

    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.

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