View 117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164
  • Recently Listed with Virtual Tour
1 of 73
$200,000
1

Beds

1.0

Baths

700

Sq.Ft.

117 Water Street N # 1B

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 132 Prospect Street Chestertown, MD MLS# MDKE2006110
  • Recently Listed
1 of 20
$189,900
2

Beds

1.0

Baths

910

Sq.Ft.

132 Prospect Street

Chestertown, MD

Bright
Courtesy of ANR REALTY, LLC
View 234 N College Avenue Chestertown, MD MLS# MDKE2005434
$164,000
2

Beds

1.0

Baths

1,296

Sq.Ft.

234 N College Avenue

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO REALTORS
The time to sell is now! THE TIME TO SELL IS NOW!
View 23069 Raleigh Road Chestertown, MD MLS# MDKE2005378
$175,000
2

Beds

0.0

Baths

1,160

Sq.Ft.

23069 Raleigh Road

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS SELECT REALTORS OF ANNAPOLIS
View Lot 9 Prestwick Drive Chestertown, MD MLS# MDKE2003918
$185,000
Studio

Beds

0.0

Baths

Lot 9 Prestwick Drive

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE

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

96

Estimated median home price

$342,400
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

Price Count
$0 - 100K 28
$100K - 200K 8
$200K - 300K 7
$300K - 400K 13
$400K - 500K 7
$500K - 600K 5
$600K - 700K 5
$700K - 800K 8
$800K - 900K 5
$900K - 1M 0
$1M - Max 10

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 31
Townhouse 6
Condo 17
Commercial 5
Rental 7
Lots and Land 36
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 3/3/2026)

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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