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 23055 Old Fairlee Road Chestertown, MD MLS# MDKE2006062
1 of 1
OPEN HOUSE: Saturday 3/7 11:00 AM - 1:00 PM
$330,000
3

Beds

2.0

Baths

1,628

Sq.Ft.

23055 Old Fairlee Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
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
The time to sell is now! THE TIME TO SELL IS NOW!
View 24775 Langford Road Chestertown, MD MLS# MDKE2005992
$319,900
3

Beds

1.0

Baths

1,008

Sq.Ft.

24775 Langford Road

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 107 Oak Leaf Drive Chestertown, MD MLS# MDKE2006114
  • Recently Listed
1 of 39
$295,000
3

Beds

2.1

Baths

1,947

Sq.Ft.

107 Oak Leaf Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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 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
View 103 Metcalf Rd Chestertown, MD MLS# MDKE2005688
  • New Construction
1 of 25
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2004650
$250,000
Studio

Beds

0.0

Baths

Scheeler Road Lot 2

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 112 Metcalf Road Chestertown, MD MLS# MDKE2006090
  • Virtual Tour
1 of 57
$249,500
3

Beds

1.1

Baths

1,280

Sq.Ft.

112 Metcalf Road

Chestertown, MD

Bright
Courtesy of ROSENDALE REALTY
View Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2004648
$225,000
Studio

Beds

0.0

Baths

Haacke Drive Lot 3

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
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 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
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 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
View Georgetown Road SE Chestertown, MD MLS# MDKE2005076
$150,000
Studio

Beds

0.0

Baths

Georgetown Road SE

Chestertown, MD

Bright
Courtesy of RE/MAX ALLEGIANCE
View Caulks Field Road Chestertown, MD MLS# MDKE2005120
$150,000
Studio

Beds

0.0

Baths

Caulks Field Road

Chestertown, MD

Bright
Courtesy of RE/MAX ALLEGIANCE
View 9925 Flatland Road Chestertown, MD MLS# MDKE2006080
$143,000
3

Beds

1.1

Baths

1,368

Sq.Ft.

9925 Flatland Road

Chestertown, MD

Bright
Courtesy of VYBE REALTY
View 423 Calvert Street Chestertown, MD MLS# MDKE2005718
$135,000
3

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

Bright
Courtesy of REDFIN CORP

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

$336,950
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

Price Count
$0 - 100K 28
$100K - 200K 9
$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 9

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 30
Townhouse 7
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 3/2/2026)

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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