View 10484 Cogar Road Chestertown, MD MLS# MDKE2007056
  • Recently Listed
1 of 22
OPEN HOUSE: Sunday 10/18 11:00 AM - 1:00 PM
$238,000
3

Beds

1.0

Baths

1,008

Sq.Ft.

10484 Cogar Road

Chestertown, MD

Bright
Courtesy of LPT REALTY, LLC
View 103 Metcalf Road Chestertown, MD MLS# MDKE2007148
  • Recently Listed
1 of 16
$259,900
3

Beds

2.1

Baths

1,280

Sq.Ft.

103 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 223 Mount Vernon Avenue Chestertown, MD MLS# MDKE2007080
$200,000
4

Beds

1.0

Baths

1,816

Sq.Ft.

223 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Towhee Road Chestertown, MD MLS# MDKE2007066
$40,000
0.0

Baths

Towhee Road

Chestertown, MD

Bright
Courtesy of THE PARKER GROUP
View 27942 Old Morgnec Road Chestertown, MD MLS# MDKE2007044
$89,000
0.0

Baths

27942 Old Morgnec Road

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 7415 Wilkins Lane Chestertown, MD MLS# MDKE2007030
$222,000
3

Beds

1.0

Baths

936

Sq.Ft.

7415 Wilkins Lane

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 104 Lincoln Drive Chestertown, MD MLS# MDKE2007032
$275,000
3

Beds

1.0

Baths

960

Sq.Ft.

104 Lincoln Drive

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 7482 Poplar Avenue Chestertown, MD MLS# MDKE2007042
$275,000
3

Beds

1.0

Baths

975

Sq.Ft.

7482 Poplar Avenue

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 115 Chester Arms Drive Chestertown, MD MLS# MDKE2006958
$259,000
3

Beds

2.0

Baths

1,140

Sq.Ft.

115 Chester Arms Drive

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View Cannon Street Chestertown, MD MLS# MDKE2006940
$196,000
0.0

Baths

Cannon Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 620 Cannon Street Chestertown, MD MLS# MDKE2006922
$85,000
0.0

Baths

620 Cannon Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 10540 Tonopah Road Chestertown, MD MLS# MDKE2006880
$269,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

10540 Tonopah Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 115 Metcalf Road Chestertown, MD MLS# MDKE2006826
  • New Construction
1 of 10
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

115 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 121 Metcalf Road Chestertown, MD MLS# MDKE2006678
  • New Construction
1 of 10
$264,900
3

Beds

1.1

Baths

121 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 21324 Persimmon Drive Chestertown, MD MLS# MDKE2006816
$179,900
2

Beds

1.0

Baths

1,232

Sq.Ft.

21324 Persimmon Drive

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 104 Conley Drive Chestertown, MD MLS# MDKE2006686
$239,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

104 Conley Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
$275,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

104 Acorn Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 234 N College Avenue Chestertown, MD MLS# MDKE2006670
$85,000
2

Beds

1.0

Baths

1,296

Sq.Ft.

234 N College Avenue

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO REALTORS
View Fairlee Road Chestertown, MD MLS# MDKE2006672
$75,000
0.0

Baths

Fairlee Road

Chestertown, MD

Bright
Courtesy of RE/MAX CHESAPEAKE
View 8886 Georgetown Road Chestertown, MD MLS# MDKE2006634
$69,900
0.0

Baths

8886 Georgetown Road

Chestertown, MD

Bright
Courtesy of SAMSON 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

128

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

PriceCount
$0 - 100K33
$100K - 200K4
$200K - 300K21
$300K - 400K21
$400K - 500K8
$500K - 600K2
$600K - 700K6
$700K - 800K10
$800K - 900K7
$900K - 1M0
$1M - Max16

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family51
Townhouse7
Condo15
Commercial12
Rental9
Lots and Land42
Condo/Town/CoOp0
CoOp0
Multi Family0
Mobile Home0
Farms1

(Data as of 10/16/2026)

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.

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