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 23110 Old Fairlee Road Chestertown, MD MLS# MDKE2005676
$349,900
3

Beds

1.0

Baths

1,805

Sq.Ft.

23110 Old Fairlee Road

Chestertown, MD

Bright
Courtesy of REAL BROKER LLC
View 8750 Georgetown Road Chestertown, MD MLS# MDKE2005834
$339,000
3

Beds

2.0

Baths

1,900

Sq.Ft.

8750 Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 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 318 Lincoln Chestertown, MD MLS# MDKE2005842
    1 of 21
    OPEN HOUSE: Saturday 12/13 12:00 PM - 3:00 PM
    $269,000
    3

    Beds

    2.0

    Baths

    960

    Sq.Ft.

    318 Lincoln

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    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 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 Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2004650
    $250,000
    Studio

    Beds

    0.0

    Baths

    Scheeler Road Lot 2

    Chestertown, MD

    Bright
    Courtesy of SELECT LAND & HOMES, 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 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
    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 Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2004648
    $225,000
    Studio

    Beds

    0.0

    Baths

    Haacke Drive Lot 3

    Chestertown, MD

    Bright
    Courtesy of SELECT LAND & HOMES, LLC
    View Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918
    $185,000
    Studio

    Beds

    0.0

    Baths

    Lot 9 Prestwick Drive

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    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 23069 Raleigh Road Chestertown, MD MLS# MDKE2005378
    $175,000
    2

    Beds

    1.1

    Baths

    1,160

    Sq.Ft.

    23069 Raleigh Road

    Chestertown, MD

    Bright
    Courtesy of KELLER WILLIAMS SELECT REALTORS OF ANNAPOLIS
    View 141 Prospect Street Chestertown, MD MLS# MDKE2005504
    $167,000
    4

    Beds

    1.1

    Baths

    1,156

    Sq.Ft.

    141 Prospect Street

    Chestertown, MD

    Bright
    Courtesy of CROSS STREET REALTORS LLC
    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 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

    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

    113

    Estimated median home price

    $350,000
    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 - 100K33
    $100K - 200K10
    $200K - 300K10
    $300K - 400K16
    $400K - 500K7
    $500K - 600K5
    $600K - 700K7
    $700K - 800K6
    $800K - 900K6
    $900K - 1M0
    $1M - Max13

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family41
    Townhouse8
    Condo13
    Commercial6
    Rental5
    Lots and Land42
    Condo/Town/CoOp0
    CoOp0
    Multi Family2
    Mobile Home0
    Farms1

    (Data as of 12/10/2025)

    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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