View Georgetown Road Chestertown, MD MLS# MDKE2005844
  • Recently Listed
1 of 7
$89,500
Studio

Beds

0.0

Baths

Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 7521 Pine Avenue Chestertown, MD MLS# MDKE2005920
  • Recently Listed
1 of 24
OPEN HOUSE: Saturday 12/6 12:00 PM - 1:00 PM
$265,000
3

Beds

1.0

Baths

1,040

Sq.Ft.

7521 Pine Avenue

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
$299,000
2

Beds

1.1

Baths

920

Sq.Ft.

611 Cannon Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 101 Metcalf Road Chestertown, MD MLS# MDKE2005882
  • New Construction
1 of 26
$264,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

101 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 318 Lincoln Chestertown, MD MLS# MDKE2005842
$269,000
3

Beds

2.0

Baths

960

Sq.Ft.

318 Lincoln

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Clarissa Road Chestertown, MD MLS# MDKE2005786
$10,000
Studio

Beds

0.0

Baths

Clarissa Road

Chestertown, MD

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Courtesy of SAMSON PROPERTIES
View 107 Malone Avenue Chestertown, MD MLS# MDKE2005764
$290,000
3

Beds

1.0

Baths

1,200

Sq.Ft.

107 Malone Avenue

Chestertown, MD

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Courtesy of DOUGLAS REALTY LLC
View 423 Calvert Street Chestertown, MD MLS# MDKE2005718
$165,000
3

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

Bright
Courtesy of REDFIN CORP
View 103 Metcalf Rd Chestertown, MD MLS# MDKE2005688
  • New Construction
1 of 25
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 21316 Persimmon Drive Chestertown, MD MLS# MDKE2005624
$179,000
2

Beds

1.0

Baths

1,232

Sq.Ft.

21316 Persimmon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 100 Metcalf Road Chestertown, MD MLS# MDKE2005634
$245,000
3

Beds

2.0

Baths

1,140

Sq.Ft.

100 Metcalf Road

Chestertown, MD

Bright
Courtesy of BAYSIDE REALTY
View 7483 Shortall Street Chestertown, MD MLS# MDKE2005616
$290,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

7483 Shortall Street

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View Buck Neck Landing Road Chestertown, MD MLS# MDKE2005586
$10,000
Studio

Beds

0.0

Baths

Buck Neck Landing Road

Chestertown, MD

Bright
Courtesy of ROSENDALE REALTY
View Tonopah Rd. Chestertown, MD MLS# MDKE2005564
$40,000
Studio

Beds

0.0

Baths

Tonopah Rd.

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View 5700 Johnsontown Road Chestertown, MD MLS# MDKE2005562
$110,000
3

Beds

1.0

Baths

1,144

Sq.Ft.

5700 Johnsontown Road

Chestertown, MD

Bright
Courtesy of TESLA REALTY GROUP, LLC
View Johnsontown Road Chestertown, MD MLS# MDKE2005550
$35,000
Studio

Beds

0.0

Baths

Johnsontown Road

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
View Sandpiper Road Chestertown, MD MLS# MDKE2005542
$9,000
Studio

Beds

0.0

Baths

Sandpiper Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 112 Metcalf Road Chestertown, MD MLS# MDKE2005498
$249,950
3

Beds

1.1

Baths

1,280

Sq.Ft.

112 Metcalf Road

Chestertown, MD

Bright
Courtesy of ENGEL & VOLKERS ANNAPOLIS
View 141 Prospect Street Chestertown, MD MLS# MDKE2005504
$167,000
4

Beds

1.1

Baths

1,156

Sq.Ft.

141 Prospect Street

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View Tonopah Road Chestertown, MD MLS# MDKE2005470
$8,000
Studio

Beds

0.0

Baths

Tonopah Road

Chestertown, MD

Bright
Courtesy of COMPASS

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

120

Estimated median home price

$320,000
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 - 100K37
$100K - 200K10
$200K - 300K11
$300K - 400K14
$400K - 500K11
$500K - 600K5
$600K - 700K8
$700K - 800K4
$800K - 900K6
$900K - 1M0
$1M - Max14

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family49
Townhouse9
Condo9
Commercial6
Rental4
Lots and Land44
Condo/Town/CoOp0
CoOp0
Multi Family2
Mobile Home0
Farms1

(Data as of 11/11/2025)

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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