View 115 Chester Arms Drive Chestertown, MD MLS# MDKE2006958
$263,000
3

Beds

2.0

Baths

1,140

Sq.Ft.

115 Chester Arms Drive

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View 101 S College Avenue Chestertown, MD MLS# MDKE2006918
$369,000
2

Beds

1.1

Baths

1,036

Sq.Ft.

101 S College Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 7982 Radcliffe Road Chestertown, MD MLS# MDKE2006950
  • Recently Listed with Virtual Tour
1 of 37
$478,000
2

Beds

2.0

Baths

1,904

Sq.Ft.

7982 Radcliffe Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 123 Trafford Drive Chestertown, MD MLS# MDKE2006934
$375,000
4

Beds

2.1

Baths

2,504

Sq.Ft.

123 Trafford Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Cannon Street Chestertown, MD MLS# MDKE2006940
  • Recently Listed
1 of 9
$350,000
Studio

Beds

0.0

Baths

Cannon Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View Cannon Street Chestertown, MD MLS# MDKE2006944
  • Recently Listed
1 of 9
$450,000
Studio

Beds

0.0

Baths

Cannon Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 216 Birch Run Road Chestertown, MD MLS# MDKE2006896
$750,000
3

Beds

2.1

Baths

2,176

Sq.Ft.

216 Birch Run Road

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 620 Cannon Street Chestertown, MD MLS# MDKE2006922
  • Recently Listed
1 of 9
$99,999
Studio

Beds

0.0

Baths

620 Cannon Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 8630 Elm Road Chestertown, MD MLS# MDKE2006914
  • Recently Listed
1 of 47
OPEN HOUSE: Sunday 8/16 12:00 PM - 3:00 PM
$445,000
5

Beds

2.1

Baths

1,936

Sq.Ft.

8630 Elm Road

Chestertown, MD

Bright
Courtesy of SAVE 6, INCORPORATED
View Sandpiper Road Chestertown, MD MLS# MDKE2006902
  • Recently Listed
1 of 8
$4,500
Studio

Beds

0.0

Baths

Sandpiper Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 104 Church Alley Chestertown, MD MLS# MDKE2006900
$440,000
2

Beds

1.1

Baths

1,058

Sq.Ft.

104 Church Alley

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 129 Trafford Drive Chestertown, MD MLS# MDKE2006878
  • Recently Listed
1 of 15
$480,000
3

Beds

2.1

Baths

3,176

Sq.Ft.

129 Trafford Drive

Chestertown, MD

Bright
Courtesy of ELEVATED REAL ESTATE SOLUTIONS
View 207 Lincoln Drive Chestertown, MD MLS# MDKE2006894
$135,000
4

Beds

1.1

Baths

1,152

Sq.Ft.

207 Lincoln Drive

Chestertown, MD

Bright
Courtesy of MONUMENT SOTHEBY'S INTERNATIONAL REALTY
View 10540 Tonopah Road Chestertown, MD MLS# MDKE2006880
  • Recently Listed
1 of 21
$279,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

10540 Tonopah Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 7903 Radcliffe Road Chestertown, MD MLS# MDKE2006890
$625,000
3

Beds

2.2

Baths

4,037

Sq.Ft.

7903 Radcliffe Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 202 Pine Street Chestertown, MD MLS# MDKE2006888
$205,000
3

Beds

1.0

Baths

1,341

Sq.Ft.

202 Pine Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 1010 Twin Court Chestertown, MD MLS# MDKE2006874
  • Recently Listed
1 of 25
$375,000
4

Beds

2.0

Baths

1,476

Sq.Ft.

1010 Twin Court

Chestertown, MD

Bright
Courtesy of KEVIN DEY REALTY
View 104 Maple Avenue Chestertown, MD MLS# MDKE2006870
  • Recently Listed
1 of 62
$650,000
7,296

Sq.Ft.

104 Maple Avenue

Chestertown, MD

Bright
Courtesy of ALEX COOPER AUCTIONEERS, INC.
View 21146 Montana Avenue Chestertown, MD MLS# MDKE2006858
$289,900
2

Beds

1.1

Baths

1,500

Sq.Ft.

21146 Montana Avenue

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 8312 Broad Neck Road Chestertown, MD MLS# MDKE2006854
$380,000
3

Beds

1.1

Baths

3,292

Sq.Ft.

8312 Broad Neck Road

Chestertown, MD

Bright
Courtesy of PEARSON SMITH REALTY, 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

129

Estimated median home price

$325,000
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 34
$100K - 200K 7
$200K - 300K 20
$300K - 400K 18
$400K - 500K 12
$500K - 600K 3
$600K - 700K 5
$700K - 800K 12
$800K - 900K 7
$900K - 1M 0
$1M - Max 11

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 48
Townhouse 11
Condo 16
Commercial 11
Rental 13
Lots and Land 43
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 8/16/2026)

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.

© 2026 BrightMLS. All Rights Reserved.