View 103 Sutton Way Chestertown, MD MLS# MDKE2006344
  • Recently Listed with Virtual Tour
1 of 53
$550,000
5

Beds

3.1

Baths

3,816

Sq.Ft.

103 Sutton Way

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 206 S Water Street Chestertown, MD MLS# MDKE2006058
$549,000
4

Beds

2.1

Baths

2,008

Sq.Ft.

206 S Water Street

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
  • Virtual Tour
1 of 41
$525,000
4

Beds

3.0

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 103 Landing Lane Chestertown, MD MLS# MDKE2005670
1 of 70
OPEN HOUSE: Saturday 4/25 10:00 AM - 12:00 PM
$519,999
2

Beds

2.1

Baths

2,100

Sq.Ft.

103 Landing Lane

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 218 Camelot Drive Chestertown, MD MLS# MDKE2005982
  • Virtual Tour
1 of 57
$510,000
5

Beds

3.1

Baths

3,932

Sq.Ft.

218 Camelot Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER REALTY
View 116 Harlan Loop Chestertown, MD MLS# MDKE2005610
$509,000
5

Beds

3.1

Baths

4,067

Sq.Ft.

116 Harlan Loop

Chestertown, MD

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Courtesy of SAMSON PROPERTIES
View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
  • Virtual Tour
1 of 53
$499,900
4

Beds

0.0

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 100 Adela Way Chestertown, MD MLS# MDKE2005636
  • Virtual Tour
1 of 71
$498,500
4

Beds

3.1

Baths

3,799

Sq.Ft.

100 Adela Way

Chestertown, MD

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$465,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

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Courtesy of RE/MAX ADVANTAGE REALTY
View 103 Trafford Drive Chestertown, MD MLS# MDKE2006416
1 of 1
OPEN HOUSE: Saturday 4/25 1:00 PM - 3:00 PM
$450,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

103 Trafford Drive

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
$445,000
3

Beds

2.1

Baths

1,857

Sq.Ft.

24295 Langford Road

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
$439,999
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 201 Birch Run Road Chestertown, MD MLS# MDKE2006316
$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 109 S College Avenue Chestertown, MD MLS# MDKE2006040
$419,900
3

Beds

2.1

Baths

1,216

Sq.Ft.

109 S College Avenue

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 104 Flying Cloud Drive Chestertown, MD MLS# MDKE2006212
$399,900
5

Beds

3.1

Baths

2,535

Sq.Ft.

104 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 349 & 351 High Street Chestertown, MD MLS# MDKE2003720
$395,000
6

Beds

0.0

Baths

349 & 351 High Street

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 349 High Street Chestertown, MD MLS# MDKE2004076
$395,000
7

Beds

3.1

Baths

3,664

Sq.Ft.

349 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 202 Waldo Drive Chestertown, MD MLS# MDKE2006260
$389,000
3

Beds

1.1

Baths

2,055

Sq.Ft.

202 Waldo Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 6746 Quaker Neck Road Chestertown, MD MLS# MDKE2006014
$384,000
5

Beds

2.1

Baths

3,371

Sq.Ft.

6746 Quaker Neck Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 6746 Quaker Road Chestertown, MD MLS# MDKE2006022
$384,000
3,371

Sq.Ft.

6746 Quaker Road

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

115

Estimated median home price

$339,000
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 14
$300K - 400K 17
$400K - 500K 8
$500K - 600K 6
$600K - 700K 6
$700K - 800K 7
$800K - 900K 7
$900K - 1M 0
$1M - Max 13

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 43
Townhouse 8
Condo 17
Commercial 9
Rental 11
Lots and Land 37
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 4/20/2026)

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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