View 203 High Street # 2 Chestertown, MD MLS# MDKE2006034
$1,600

203 High Street # 2

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 200A High Chestertown, MD MLS# MDKE2005996
  • Recently Listed
1 of 17
$2,500

200A High

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 302 Park Row # OFFICE 2 Chestertown, MD MLS# MDKE2005598
$600

302 Park Row # OFFICE 2

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 601 Washington Avenue Chestertown, MD MLS# MDKE2004736
$2,864
13,500

Sq.Ft.

601 Washington Avenue

Chestertown, MD

Bright
Courtesy of SVN/MILLER COMMERCIAL REAL ESTATE
View 22600 Fairgale Farm Lane Chestertown, MD MLS# MDKE2003204
$6,000
5

Beds

4.1

Baths

4,033

Sq.Ft.

22600 Fairgale Farm Lane

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 101 Morgnec Road Chestertown, MD MLS# MDKE113944
$1,300
1

Beds

1.0

Baths

785

Sq.Ft.

101 Morgnec Road

Chestertown, MD

Bright
Courtesy of DAVIS REAL ESTATE, INC.

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

108

Estimated median home price

$333,950
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 - 200K8
$200K - 300K10
$300K - 400K16
$400K - 500K8
$500K - 600K5
$600K - 700K5
$700K - 800K6
$800K - 900K5
$900K - 1M0
$1M - Max12

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family40
Townhouse8
Condo12
Commercial5
Rental6
Lots and Land41
Condo/Town/CoOp0
CoOp0
Multi Family1
Mobile Home0
Farms1

(Data as of 1/11/2026)

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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