View 349 & 351 High Street Chestertown, MD MLS# MDKE2003720
$395,000
6

Beds

0.0

Baths

349 & 351 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 349 High Street Chestertown, MD MLS# MDKE2004076
$395,000
7

Beds

3.1

Baths

3,664

Sq.Ft.

349 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 860 & 870 High Street Chestertown, MD MLS# MDKE2003850
$375,000
16,977

Sq.Ft.

860 & 870 High Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
The time to sell is now! THE TIME TO SELL IS NOW!
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 204 Rolling Road Chestertown, MD MLS# MDKE2005896
$370,000
3

Beds

2.0

Baths

2,296

Sq.Ft.

204 Rolling Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 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 112 Silver Heel Drive Chestertown, MD MLS# MDKE2005880
$369,900
5

Beds

3.1

Baths

2,615

Sq.Ft.

112 Silver Heel Drive

Chestertown, MD

Bright
Courtesy of EXP REALTY, LLC
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 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 303 E Campus Avenue Chestertown, MD MLS# MDKE2005756
$363,000
3

Beds

2.0

Baths

1,532

Sq.Ft.

303 E Campus Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
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
$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 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 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 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 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
    $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

    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

    108

    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 - 100K34
    $100K - 200K8
    $200K - 300K10
    $300K - 400K16
    $400K - 500K6
    $500K - 600K5
    $600K - 700K6
    $700K - 800K6
    $800K - 900K6
    $900K - 1M0
    $1M - Max11

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family39
    Townhouse8
    Condo12
    Commercial5
    Rental5
    Lots and Land42
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms1

    (Data as of 12/29/2025)

    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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