View 23683 L Road Chestertown, MD MLS# MDKE2006580
$6,000
Studio

Beds

0.0

Baths

23683 L Road

Chestertown, MD

Bright
Courtesy of ALEX COOPER AUCTIONEERS, INC.
View 21363 Lynn Lane Chestertown, MD MLS# MDKE2006556
$205,000
3

Beds

1.0

Baths

1,314

Sq.Ft.

21363 Lynn Lane

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 304 Hadaway Drive Chestertown, MD MLS# MDKE2006482
$314,900
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of REDFIN CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View Sandy Bottom Road Chestertown, MD MLS# MDKE2006554
$79,000
Studio

Beds

0.0

Baths

Sandy Bottom Road

Chestertown, MD

Bright
Courtesy of VILLAGE REAL ESTATE COMPANY LLC
View 100 Prospect Street Chestertown, MD MLS# MDKE2006544
$215,000
3

Beds

1.0

Baths

1,373

Sq.Ft.

100 Prospect Street

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 110 S Queen Street Chestertown, MD MLS# MDKE2006536
$525,000
1,785

Sq.Ft.

110 S Queen Street

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 8629 Airy Hill Road Chestertown, MD MLS# MDKE2006526
$425,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

8629 Airy Hill Road

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS REALTY
View 1014 Twin Court Chestertown, MD MLS# MDKE2006516
$499,000
3

Beds

2.0

Baths

1,817

Sq.Ft.

1014 Twin Court

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 110 S Queen Street Chestertown, MD MLS# MDKE2006520
$525,000
3

Beds

1.1

Baths

1,785

Sq.Ft.

110 S Queen Street

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 107 Flying Cloud Drive Chestertown, MD MLS# MDKE2006510
$385,000
5

Beds

3.1

Baths

2,534

Sq.Ft.

107 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 214 Silver Heel Road Chestertown, MD MLS# MDKE2006498
$340,000
4

Beds

2.1

Baths

1,972

Sq.Ft.

214 Silver Heel Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 144 Prospect Street Chestertown, MD MLS# MDKE2006494
$159,000
2

Beds

1.1

Baths

1,082

Sq.Ft.

144 Prospect Street

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 9816 Fairlee Road Chestertown, MD MLS# MDKE2006488
$535,000
3

Beds

3.0

Baths

1,624

Sq.Ft.

9816 Fairlee Road

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 23416 Cloquet Road Chestertown, MD MLS# MDKE2006486
$384,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

23416 Cloquet Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342
$229,990
3

Beds

2.0

Baths

1,352

Sq.Ft.

24581 Willow Oak Lane

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 116 Cross Street Chestertown, MD MLS# MDKE2006420
$109,999
Studio

Beds

0.0

Baths

116 Cross Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 103 Metcalf Rd Chestertown, MD MLS# MDKE2006446
  • New Construction
1 of 22
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 103 Trafford Drive Chestertown, MD MLS# MDKE2006416
    1 of 67
    OPEN HOUSE: Saturday 6/20 11:00 AM - 1:00 PM
    $399,900
    3

    Beds

    2.1

    Baths

    1,944

    Sq.Ft.

    103 Trafford Drive

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 8706 Elm Road Chestertown, MD MLS# MDKE2006390
    $320,000
    3

    Beds

    2.0

    Baths

    1,232

    Sq.Ft.

    8706 Elm Road

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
    $430,000
    2

    Beds

    2.1

    Baths

    1,857

    Sq.Ft.

    24295 Langford Road

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, 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

    127

    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 - 100K32
    $100K - 200K10
    $200K - 300K15
    $300K - 400K17
    $400K - 500K13
    $500K - 600K5
    $600K - 700K4
    $700K - 800K8
    $800K - 900K6
    $900K - 1M0
    $1M - Max17

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family54
    Townhouse7
    Condo16
    Commercial10
    Rental14
    Lots and Land40
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 6/20/2026)

    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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