View 301 E CAMPUS AVENUE Chestertown, MD MLS# MDKE118138
$250,000
3

Beds

2.0

Baths

1,398

Sq.Ft.

301 E CAMPUS AVENUE

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 6769 QUAKER NECK ROAD Chestertown, MD MLS# MDKE118128
$82,000
3

Beds

1.0

Baths

1,040

Sq.Ft.

6769 QUAKER NECK ROAD

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 7546 POPLAR AVENUE Chestertown, MD MLS# MDKE118094
  • Recently Listed
1 of 21
$235,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

7546 POPLAR AVENUE

Chestertown, MD

Bright
Courtesy of ROSENDALE REALTY
View 7431 MAPLE GROVE ROAD Chestertown, MD MLS# MDKE118122
$1,400,000
3

Beds

3.2

Baths

5,595

Sq.Ft.

7431 MAPLE GROVE ROAD

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 25320 FOX CHASE DRIVE Chestertown, MD MLS# MDKE118118
  • Recently Listed with Virtual Tour
1 of 28
$529,000
3

Beds

3.0

Baths

2,160

Sq.Ft.

25320 FOX CHASE DRIVE

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 110 CONLEY DRIVE Chestertown, MD MLS# MDKE118068
$159,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

110 CONLEY DRIVE

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 110 ELM STREET Chestertown, MD MLS# MDKE118000
$282,000
3

Beds

2.0

Baths

1,267

Sq.Ft.

110 ELM STREET

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8970 CUMBERLAND STREET Chestertown, MD MLS# MDKE118002
$149,000
2

Beds

2.0

Baths

840

Sq.Ft.

8970 CUMBERLAND STREET

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 500 MORGNEC ROAD Chestertown, MD MLS# MDKE118108
  • Recently Listed
1 of 9
$395,000
0.0

Baths

500 MORGNEC ROAD

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 306 ROOSEVELT DRIVE Chestertown, MD MLS# MDKE118074
$199,999
3

Beds

1.1

Baths

1,152

Sq.Ft.

306 ROOSEVELT DRIVE

Chestertown, MD

Bright
Courtesy of EXIT PREFERRED REALTY
View 101 LANDING LANE Chestertown, MD MLS# MDKE118082
  • Recently Listed
1 of 32
$550,000
3

Beds

3.1

Baths

3,300

Sq.Ft.

101 LANDING LANE

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 11138 PERKINS HILL ROAD Chestertown, MD MLS# MDKE117978
$285,000
3

Beds

2.0

Baths

3,637

Sq.Ft.

11138 PERKINS HILL ROAD

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 405 CALVERT STREET Chestertown, MD MLS# MDKE118084
  • Recently Listed
1 of 14
$99,900
3

Beds

1.1

Baths

1,136

Sq.Ft.

405 CALVERT STREET

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 105 N WATER STREET Chestertown, MD MLS# MDKE118076
  • Recently Listed
1 of 27
$470,000
2

Beds

2.0

Baths

1,098

Sq.Ft.

105 N WATER STREET

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 103 CONLEY DRIVE Chestertown, MD MLS# MDKE118072
  • Recently Listed
1 of 6
$219,900
3

Beds

1.1

Baths

1,260

Sq.Ft.

103 CONLEY DRIVE

Chestertown, MD

Bright
Courtesy of D N K REAL ESTATE, LLC
View 10401 BUNTING ROAD Chestertown, MD MLS# MDKE118026
  • Recently Listed
1 of 16
$220,000
4

Beds

2.0

Baths

1,248

Sq.Ft.

10401 BUNTING ROAD

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS FLAGSHIP OF MARYLAND
View 519 N KENT STREET Chestertown, MD MLS# MDKE118056
$399,000
4

Beds

3.0

Baths

2,200

Sq.Ft.

519 N KENT STREET

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 21340 PERSIMMON DRIVE Chestertown, MD MLS# MDKE118052
  • Recently Listed with Virtual Tour
1 of 41
$121,900
2

Beds

1.0

Baths

1,269

Sq.Ft.

21340 PERSIMMON DRIVE

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 7434 CEDAR ROAD Chestertown, MD MLS# MDKE118042
$217,000
3

Beds

2.0

Baths

1,224

Sq.Ft.

7434 CEDAR ROAD

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 316 LANDING LANE Chestertown, MD MLS# MDKE118016
$700,000
3

Beds

2.1

Baths

316 LANDING LANE

Chestertown, MD

Bright
Courtesy of CROSS STREET 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

105

Estimated median home price

$285,000
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 - 200K21
$200K - 300K30
$300K - 400K14
$400K - 500K4
$500K - 600K4
$600K - 700K5
$700K - 800K2
$800K - 900K3
$900K - 1M2
$1M - Max15

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family50
Townhouse15
Condo4
Commercial13
Rental3
Lots and Land21
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms2

(Data as of 5/16/2021)

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.

© 2021 BrightMLS. All Rights Reserved.