View 23698 L Road Chestertown, MD MLS# MDKE2005988
$24,000
Studio

Beds

0.0

Baths

23698 L Road

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 218 Camelot Drive Chestertown, MD MLS# MDKE2005982
$525,000
5

Beds

3.1

Baths

3,932

Sq.Ft.

218 Camelot Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 109 Metcalf Road Chestertown, MD MLS# MDKE2005968
  • New Construction
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
The time to sell is now! THE TIME TO SELL IS NOW!
View Cloquet Road Chestertown, MD MLS# MDKE2005966
  • Virtual Tour
1 of 32
$39,000
Studio

Beds

0.0

Baths

Cloquet Road

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$475,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
  • Virtual Tour
1 of 40
OPEN HOUSE: Saturday 3/14 11:00 AM - 1:00 PM
$580,000
5

Beds

3.1

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
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 108 Little Harbor Way Chestertown, MD MLS# MDKE2005902
$635,000
Studio

Beds

0.0

Baths

108 Little Harbor Way

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
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
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
$449,999
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
$499,900
4

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, 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 Clarissa Road Chestertown, MD MLS# MDKE2005786
$10,000
Studio

Beds

0.0

Baths

Clarissa Road

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View 100 Adela Way Chestertown, MD MLS# MDKE2005636
  • Virtual Tour
1 of 71
OPEN HOUSE: Sunday 3/15 11:00 AM - 1:00 PM
$498,500
4

Beds

3.1

Baths

3,799

Sq.Ft.

100 Adela Way

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
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 103 Landing Lane Chestertown, MD MLS# MDKE2005670
    1 of 70
    OPEN HOUSE: Saturday 3/14 10:00 AM - 12:00 PM
    $539,999
    2

    Beds

    2.1

    Baths

    2,100

    Sq.Ft.

    103 Landing Lane

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    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 116 Harlan Loop Chestertown, MD MLS# MDKE2005610
    $509,000
    5

    Beds

    3.1

    Baths

    4,067

    Sq.Ft.

    116 Harlan Loop

    Chestertown, MD

    Bright
    Courtesy of SAMSON PROPERTIES

    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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