106 total properties
View 6746 Quaker Road Chestertown, MD MLS# MDKE2006022
$445,000
3,371

Sq.Ft.

6746 Quaker Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 121 Primrose Road Chestertown, MD MLS# MDQA2015570
$350,000
3

Beds

2.1

Baths

2,034

Sq.Ft.

121 Primrose Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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# MDKE2006116
$344,900
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
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 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 129 Parma Road Chestertown, MD MLS# MDQA2015862
$330,000
3

Beds

2.0

Baths

1,170

Sq.Ft.

129 Parma Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
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 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 222 Dutchess Road Chestertown, MD MLS# MDQA2014830
$320,000
3

Beds

1.1

Baths

1,096

Sq.Ft.

222 Dutchess Road

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
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 ADVANTAGE REALTY
View 213 Central Drive Chestertown, MD MLS# MDQA2015648
$314,900
3

Beds

2.0

Baths

1,232

Sq.Ft.

213 Central Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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 Oak Leaf Drive Chestertown, MD MLS# MDKE2006114
    1 of 39
    OPEN HOUSE: Sunday 3/1 12:00 PM - 2:00 PM
    $295,000
    3

    Beds

    2.1

    Baths

    1,947

    Sq.Ft.

    107 Oak Leaf Drive

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 119 Darden Road Chestertown, MD MLS# MDQA2016084
    $275,000
    3

    Beds

    2.0

    Baths

    1,424

    Sq.Ft.

    119 Darden Road

    Chestertown, MD

    Bright
    Courtesy of COMPASS

    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.