View 22481 Goose Hollow Drive Chestertown, MD MLS# MDKE2006682
$279,900
3

Beds

2.0

Baths

1,296

Sq.Ft.

22481 Goose Hollow Drive

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS LEGACY
View 104 Conley Drive Chestertown, MD MLS# MDKE2006686
  • Recently Listed
1 of 27
$247,000
3

Beds

1.1

Baths

1,280

Sq.Ft.

104 Conley Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
  • Recently Listed
1 of 26
OPEN HOUSE: Saturday 6/27 10:00 AM - 12:00 PM
$284,900
3

Beds

2.1

Baths

1,900

Sq.Ft.

104 Acorn Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 10572 Watonga Road Chestertown, MD MLS# MDKE2006644
$325,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

10572 Watonga Road

Chestertown, MD

Bright
Courtesy of SERHANT
View 956 Washington Avenue Chestertown, MD MLS# MDKE2006394
$285,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

956 Washington Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 304 Hadaway Drive Chestertown, MD MLS# MDKE2006482
$309,900
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of REDFIN CORPORATION
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 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 10584 Klamath Road Chestertown, MD MLS# MDKE2006328
  • New Construction
1 of 20
$319,900
3

Beds

1.1

Baths

10584 Klamath Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290
$250,000
Studio

Beds

0.0

Baths

Scheeler Road Lot 2

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298
$250,000
37,026

Sq.Ft.

Scheeler Road Lot 2

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
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

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

124

Estimated median home price

$345,000
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 - 300K14
$300K - 400K14
$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 Family50
Townhouse7
Condo17
Commercial10
Rental15
Lots and Land40
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms0

(Data as of 6/26/2026)

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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