View 10594 Millbrook Drive Chestertown, MD MLS# MDKE2006378
$329,000
3

Beds

2.0

Baths

1,499

Sq.Ft.

10594 Millbrook Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, 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
View 217 Philosophers Terrace Chestertown, MD MLS# MDKE2006332
$325,000
3

Beds

1.1

Baths

1,404

Sq.Ft.

217 Philosophers Terrace

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
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 10584 Klamath Road Chestertown, MD MLS# MDKE2006328
  • New Construction
1 of 20
$319,900
2

Beds

2.0

Baths

10584 Klamath Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 301 Lincoln Drive Chestertown, MD MLS# MDKE2006170
  • Virtual Tour
1 of 40
$309,900
3

Beds

2.0

Baths

1,152

Sq.Ft.

301 Lincoln Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 115 Acorn Drive Chestertown, MD MLS# MDKE2006360
$296,000
2

Beds

2.1

Baths

1,864

Sq.Ft.

115 Acorn Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, 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
View 112 Elm Street Chestertown, MD MLS# MDKE2006192
$269,900
3

Beds

1.0

Baths

1,356

Sq.Ft.

112 Elm Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER WATERMAN REALTY
View 21217 Texas Avenue Chestertown, MD MLS# MDKE2006364
  • Recently Listed
1 of 20
$265,000
2

Beds

1.0

Baths

912

Sq.Ft.

21217 Texas Avenue

Chestertown, MD

Bright
Courtesy of RE/MAX LEADING EDGE
View 109 Metcalf Road Chestertown, MD MLS# MDKE2005968
  • New Construction
1 of 28
$264,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

109 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 107 Metcalf Road Chestertown, MD MLS# MDKE2006186
  • New Construction
1 of 17
$259,900
3

Beds

2.0

Baths

1,200

Sq.Ft.

107 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290
  • Recently Listed
1 of 4
$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
  • Recently Listed
1 of 4
$250,000
37,026

Sq.Ft.

Scheeler Road Lot 2

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 139 Prospect Street Chestertown, MD MLS# MDKE2006250
  • Recently Listed
1 of 28
$225,000
3

Beds

1.0

Baths

1,200

Sq.Ft.

139 Prospect Street

Chestertown, MD

Bright
Courtesy of REDFIN CORP
View Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274
  • Recently Listed
1 of 7
$225,000
Studio

Beds

0.0

Baths

Haacke Drive Lot 3

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006302
  • Recently Listed
1 of 4
$225,000

Haacke Drive Lot 3

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 117 Water Street N # 1B Chestertown, MD MLS# MDKE2006164
$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 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 107 Conley Drive Chestertown, MD MLS# MDKE2006220
$170,000
3

Beds

1.0

Baths

1,140

Sq.Ft.

107 Conley Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, 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

112

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

Price Count
$0 - 100K 29
$100K - 200K 8
$200K - 300K 11
$300K - 400K 17
$400K - 500K 9
$500K - 600K 6
$600K - 700K 6
$700K - 800K 7
$800K - 900K 7
$900K - 1M 0
$1M - Max 12

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 43
Townhouse 6
Condo 17
Commercial 8
Rental 8
Lots and Land 37
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 4/14/2026)

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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