View 212 MOUNT VERNON AVENUE Chestertown, MD MLS# MDKE2001876
$349,000
3

Beds

2.0

Baths

1,705

Sq.Ft.

212 MOUNT VERNON AVENUE

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 329 CANNON STREET Chestertown, MD MLS# MDKE2001918
  • Recently Listed
1 of 45
$525,000
0.0

Baths

2,566

Sq.Ft.

329 CANNON STREET

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 24025 CHESTERTOWN ROAD Chestertown, MD MLS# MDKE2001964
$99,900
3

Beds

1.0

Baths

1,408

Sq.Ft.

24025 CHESTERTOWN ROAD

Chestertown, MD

Bright
Courtesy of ANR REALTY, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 27336 PRESTON LANE Chestertown, MD MLS# MDKE2001924
$450,000
3

Beds

2.0

Baths

1,770

Sq.Ft.

27336 PRESTON LANE

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 110 ELM STREET Chestertown, MD MLS# MDKE2001856
$340,000
3

Beds

2.0

Baths

1,267

Sq.Ft.

110 ELM STREET

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 225 WASHINGTON AVENUE Chestertown, MD MLS# MDKE2001858
$490,000
5

Beds

3.0

Baths

2,536

Sq.Ft.

225 WASHINGTON AVENUE

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 206 BARROLL DRIVE Chestertown, MD MLS# MDKE2001726
  • Recently Listed
1 of 29
$369,500
3

Beds

2.0

Baths

1,820

Sq.Ft.

206 BARROLL DRIVE

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY INC.
View 200 COURT STREET Chestertown, MD MLS# MDKE2001848
  • Recently Listed
1 of 19
$299,000
3

Beds

2.1

Baths

1,503

Sq.Ft.

200 COURT STREET

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 100 CHURCH ALLEY Chestertown, MD MLS# MDKE2001832
  • Recently Listed
1 of 11
$239,000
0.0

Baths

960

Sq.Ft.

100 CHURCH ALLEY

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View 102 CHURCH ALLEY Chestertown, MD MLS# MDKE2001834
  • Recently Listed
1 of 10
$249,000
0.0

Baths

1,456

Sq.Ft.

102 CHURCH ALLEY

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View 21362 LYNN LANE Chestertown, MD MLS# MDKE2001810
$158,000
2

Beds

1.0

Baths

1,098

Sq.Ft.

21362 LYNN LANE

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 206 LEEDS COURT Chestertown, MD MLS# MDKE2001802
$499,900
4

Beds

3.1

Baths

2,693

Sq.Ft.

206 LEEDS COURT

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 521 HIGH STREET Chestertown, MD MLS# MDKE2001798
$349,000
3

Beds

1.1

Baths

1,356

Sq.Ft.

521 HIGH STREET

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 626 HIGH STREET Chestertown, MD MLS# MDKE2001774
$360,000
4

Beds

1.1

Baths

1,855

Sq.Ft.

626 HIGH STREET

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 246 DEVON DRIVE Chestertown, MD MLS# MDKE2001776
  • Price Reduced with Virtual Tour
1 of 50
$385,000
4

Beds

2.1

Baths

2,204

Sq.Ft.

246 DEVON DRIVE

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 10720 AUGUSTINE HERMAN HIGHWAY Chestertown, MD MLS# MDKE2001724
$399,000
2.0

Baths

3,424

Sq.Ft.

10720 AUGUSTINE HERMAN HIGHWAY

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 218 CAMELOT DRIVE Chestertown, MD MLS# MDKE2001686
$452,500
5

Beds

3.1

Baths

3,932

Sq.Ft.

218 CAMELOT DRIVE

Chestertown, MD

Bright
Courtesy of NORTHROP REALTY
View 104 MAPLE AVENUE Chestertown, MD MLS# MDKE2001754
$500,000
0.0

Baths

7,296

Sq.Ft.

104 MAPLE AVENUE

Chestertown, MD

Bright
Courtesy of ALEX COOPER AUCTIONEERS, INC.
View 111 CHESTER ARMS DRIVE Chestertown, MD MLS# MDKE2001742
$229,900
3

Beds

1.1

Baths

1,140

Sq.Ft.

111 CHESTER ARMS DRIVE

Chestertown, MD

Bright
Courtesy of D N K REAL ESTATE, LLC
View 527 HIGH STREET Chestertown, MD MLS# MDKE2001670
$349,000
2

Beds

2.0

Baths

1,124

Sq.Ft.

527 HIGH STREET

Chestertown, MD

Bright
Courtesy of MARYLAND HERITAGE PROPERTIES

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

56

Estimated median home price

$399,000
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

PriceCount
$0 - 100K5
$100K - 200K6
$200K - 300K9
$300K - 400K9
$400K - 500K9
$500K - 600K4
$600K - 700K1
$700K - 800K1
$800K - 900K1
$900K - 1M5
$1M - Max6

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family27
Townhouse4
Condo1
Commercial11
Rental5
Lots and Land11
Condo/Town/CoOp0
CoOp1
Multi Family1
Mobile Home0
Farms0

(Data as of 9/26/2022)

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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