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
$275,000
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
Studio

Beds

0.0

Baths

2,296

Sq.Ft.

204 Rolling Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
The time to sell is now! THE TIME TO SELL IS NOW!
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
    1 of 30
    OPEN HOUSE: Sunday 3/15 11:00 AM - 1:00 PM
    $444,999
    4

    Beds

    2.0

    Baths

    1,656

    Sq.Ft.

    222 Mount Vernon Avenue

    Chestertown, MD

    Bright
    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    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 23110 Old Fairlee Road Chestertown, MD MLS# MDKE2005676
    $339,900
    3

    Beds

    1.0

    Baths

    1,805

    Sq.Ft.

    23110 Old Fairlee Road

    Chestertown, MD

    Bright
    Courtesy of REAL BROKER 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 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 234 N College Avenue Chestertown, MD MLS# MDKE2005434
    $164,000
    2

    Beds

    1.0

    Baths

    1,296

    Sq.Ft.

    234 N College Avenue

    Chestertown, MD

    Bright
    Courtesy of CUMMINGS & CO REALTORS
    View Kinglet Road Chestertown, MD MLS# MDKE2005260
    $9,000
    Studio

    Beds

    0.0

    Baths

    Kinglet Road

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View Buck Neck Road Chestertown, MD MLS# MDKE2005262
    $9,000
    Studio

    Beds

    0.0

    Baths

    Buck Neck Road

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View Georgetown Rd Chestertown, MD MLS# MDKE2005218
    $60,000
    Studio

    Beds

    0.0

    Baths

    Georgetown Rd

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    View Caulks Field Road Chestertown, MD MLS# MDKE2005120
    $150,000
    Studio

    Beds

    0.0

    Baths

    Caulks Field Road

    Chestertown, MD

    Bright
    Courtesy of RE/MAX ALLEGIANCE
    View Georgetown Road SE Chestertown, MD MLS# MDKE2005076
    $150,000
    Studio

    Beds

    0.0

    Baths

    Georgetown Road SE

    Chestertown, MD

    Bright
    Courtesy of RE/MAX ALLEGIANCE
    View Old Morgnec Road Chestertown, MD MLS# MDKE2004974
    $59,000
    Studio

    Beds

    0.0

    Baths

    Old Morgnec Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View Towhee Road Chestertown, MD MLS# MDKE2004882
    $5,000
    Studio

    Beds

    0.0

    Baths

    Towhee Road

    Chestertown, MD

    Bright
    Courtesy of ASHLAND AUCTION GROUP 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

    97

    Estimated median home price

    $339,900
    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 - 100K28
    $100K - 200K7
    $200K - 300K8
    $300K - 400K14
    $400K - 500K7
    $500K - 600K6
    $600K - 700K5
    $700K - 800K8
    $800K - 900K5
    $900K - 1M0
    $1M - Max9

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family32
    Townhouse6
    Condo17
    Commercial5
    Rental7
    Lots and Land36
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms0

    (Data as of 3/12/2026)

    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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