View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
$445,000
3

Beds

2.1

Baths

1,857

Sq.Ft.

24295 Langford Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
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 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 226 S Water Street Chestertown, MD MLS# MDKE2006354
  • Recently Listed
1 of 32
$898,000
3

Beds

3.1

Baths

2,172

Sq.Ft.

226 S Water Street

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 327 Cannon Street Chestertown, MD MLS# MDKE2006104
  • Recently Listed
1 of 39
$1,300,000
3,518

Sq.Ft.

327 Cannon Street

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 25475 Turnberry Court Chestertown, MD MLS# MDKE2006350
1 of 11
OPEN HOUSE: Saturday 4/18 11:00 AM - 1:00 PM
$867,000
4

Beds

3.0

Baths

4,145

Sq.Ft.

25475 Turnberry Court

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 103 Sutton Way Chestertown, MD MLS# MDKE2006344
  • Recently Listed with Virtual Tour
1 of 53
$550,000
4

Beds

3.1

Baths

3,816

Sq.Ft.

103 Sutton Way

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 10087 John Carvill Road Chestertown, MD MLS# MDKE2006324
  • Recently Listed with Virtual Tour
1 of 63
$695,000
3

Beds

2.0

Baths

1,566

Sq.Ft.

10087 John Carvill Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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
View 108 Pine Street Chestertown, MD MLS# MDKE2006322
$115,000
3

Beds

1.0

Baths

910

Sq.Ft.

108 Pine Street

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
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 201 Birch Run Road Chestertown, MD MLS# MDKE2006316
  • Recently Listed
1 of 24
$435,000
3

Beds

2.0

Baths

1,588

Sq.Ft.

201 Birch Run Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Cogar Road Chestertown, MD MLS# MDKE2006304
  • Recently Listed
1 of 3
$3,000
Studio

Beds

0.0

Baths

Cogar Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View 103 Flying Cloud Drive Chestertown, MD MLS# MDKE2006154
$339,900
3

Beds

2.1

Baths

1,724

Sq.Ft.

103 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of AMERICAN PREMIER REALTY, 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 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 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

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

111

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 16
$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 42
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 4/11/2026)

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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