View Millbrook Drive Chestertown, MD MLS# MDKE2004060
$12,500
Studio

Beds

0.0

Baths

Millbrook Drive

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View Buck Neck Landing Road Chestertown, MD MLS# MDKE2004072
$9,500
Studio

Beds

0.0

Baths

Buck Neck Landing Road

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 106 Silver Heel Road Chestertown, MD MLS# MDKE2004074
$360,000
3

Beds

2.1

Baths

1,672

Sq.Ft.

106 Silver Heel Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 213 Devon Drive Chestertown, MD MLS# MDKE2004066
  • Recently Listed
1 of 23
$360,000
4

Beds

2.1

Baths

2,472

Sq.Ft.

213 Devon Drive

Chestertown, MD

Bright
Courtesy of Martinsburg - WEICHERT, REALTORS® - Blue Ribbon
View 101 Landing Lane # 39 Chestertown, MD MLS# MDKE2004058
$699,999
3

Beds

3.1

Baths

3,300

Sq.Ft.

101 Landing Lane # 39

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 10572 Klamath Road Chestertown, MD MLS# MDKE2004062
$269,900
3

Beds

2.0

Baths

1,232

Sq.Ft.

10572 Klamath Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 23795 Lands End Road Chestertown, MD MLS# MDKE2004046
  • Recently Listed
1 of 24
$267,000
3

Beds

3.0

Baths

2,088

Sq.Ft.

23795 Lands End Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 807 S Meadowview Drive Chestertown, MD MLS# MDKE2004028
$424,900
4

Beds

2.1

Baths

2,464

Sq.Ft.

807 S Meadowview Drive

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View Buck Neck Road Chestertown, MD MLS# MDKE2004038
  • Recently Listed
1 of 2
$9,000
Studio

Beds

0.0

Baths

Buck Neck Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 129A Manor Avenue Chestertown, MD MLS# MDKE2004012
  • Virtual Tour
1 of 32
$245,000
3

Beds

2.0

Baths

960

Sq.Ft.

129A Manor Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Vireo Road Chestertown, MD MLS# MDKE2004034
  • Recently Listed
1 of 7
$35,000
Studio

Beds

0.0

Baths

Vireo Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8858 Georgetown Road Chestertown, MD MLS# MDKE2004008
$325,000
3

Beds

2.0

Baths

1,300

Sq.Ft.

8858 Georgetown Road

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS SELECT REALTORS
View 10589 Klamath Road Chestertown, MD MLS# MDKE2004026
  • Recently Listed with Virtual Tour
1 of 33
$269,900
3

Beds

2.0

Baths

1,326

Sq.Ft.

10589 Klamath Road

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 128 N Queen Street Chestertown, MD MLS# MDKE2003998
$599,000
4

Beds

5.0

Baths

3,497

Sq.Ft.

128 N Queen Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 307 Washington Avenue Chestertown, MD MLS# MDKE2003972
  • Recently Listed
1 of 86
$879,000
4

Beds

3.1

Baths

3,355

Sq.Ft.

307 Washington Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 23530 Clarissa Road Chestertown, MD MLS# MDKE2003944
$345,000
3

Beds

2.0

Baths

1,812

Sq.Ft.

23530 Clarissa Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 106 Pine Street Chestertown, MD MLS# MDKE2003962
  • Virtual Tour
1 of 30
$264,975
3

Beds

1.0

Baths

1,376

Sq.Ft.

106 Pine Street

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 22939 Bay Shore Road Chestertown, MD MLS# MDKE2003964
$319,000
3

Beds

2.0

Baths

1,505

Sq.Ft.

22939 Bay Shore Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Lot 4 Muirfield Drive Chestertown, MD MLS# MDKE2003924
1 of 22
OPEN HOUSE: Sunday 6/2 12:00 PM - 2:30 PM
$175,000
Studio

Beds

0.0

Baths

Lot 4 Muirfield Drive

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 7514 Muirfield Drive Chestertown, MD MLS# MDKE2003926
  • New Construction
1 of 20
OPEN HOUSE: Sunday 6/2 12:00 PM - 3:00 PM
$798,000
3

Beds

2.1

Baths

7514 Muirfield Drive

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE

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

87

Estimated median home price

$275,000
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 31
$100K - 200K 4
$200K - 300K 10
$300K - 400K 8
$400K - 500K 7
$500K - 600K 1
$600K - 700K 2
$700K - 800K 4
$800K - 900K 7
$900K - 1M 5
$1M - Max 8

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 37
Townhouse 4
Condo 5
Commercial 4
Rental 13
Lots and Land 35
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 0

(Data as of 6/1/2024)

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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