View 22974 Bay Shore Road Chestertown, MD MLS# MDKE2007106
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$329,900
2

Beds

2.0

Baths

1,440

Sq.Ft.

22974 Bay Shore Road

Chestertown, MD

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View 896 Washington Avenue Chestertown, MD MLS# MDKE2006750
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$325,000
3

Beds

1.0

Baths

1,000

Sq.Ft.

896 Washington Avenue

Chestertown, MD

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View 200 Manor Avenue Chestertown, MD MLS# MDKE2006808
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$325,000
4

Beds

2.0

Baths

2,198

Sq.Ft.

200 Manor Avenue

Chestertown, MD

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The time to sell is now! THE TIME TO SELL IS NOW!
View 896 Washington Avenue Chestertown, MD MLS# MDKE2007140
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$325,000
1,000

Sq.Ft.

896 Washington Avenue

Chestertown, MD

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View 8706 Elm Road Chestertown, MD MLS# MDKE2006390
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$315,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

8706 Elm Road

Chestertown, MD

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View 24775 Langford Road Chestertown, MD MLS# MDKE2007012
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$315,000
3

Beds

1.0

Baths

1,008

Sq.Ft.

24775 Langford Road

Chestertown, MD

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View 9126 Fairlee Road Chestertown, MD MLS# MDKE2006764
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$314,000
3

Beds

1.1

Baths

1,216

Sq.Ft.

9126 Fairlee Road

Chestertown, MD

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View 7464 Shortall Street Chestertown, MD MLS# MDKE2006988
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$304,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

7464 Shortall Street

Chestertown, MD

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View 201 N Lynchburg Street # LOTS 4, 5, 6 & 7 Chestertown, MD MLS# MDKE2006846
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$300,000
0.0

Baths

201 N Lynchburg Street # LOTS 4, 5, 6 & 7

Chestertown, MD

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View 8732 Elm Road Chestertown, MD MLS# MDKE2007082
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OPEN HOUSE: Saturday 10/3 2:00 PM - 3:30 PM
$289,000
3

Beds

2.0

Baths

1,056

Sq.Ft.

8732 Elm Road

Chestertown, MD

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View 104 Lincoln Drive Chestertown, MD MLS# MDKE2007032
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OPEN HOUSE: Saturday 10/3 10:00 AM - 12:00 PM
$285,000
3

Beds

1.0

Baths

960

Sq.Ft.

104 Lincoln Drive

Chestertown, MD

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View Cannon Street Chestertown, MD MLS# MDKE2006944
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$281,000
0.0

Baths

Cannon Street

Chestertown, MD

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View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
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$275,000
2

Beds

1.1

Baths

920

Sq.Ft.

611 Cannon Street

Chestertown, MD

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View 956 Washington Avenue Chestertown, MD MLS# MDKE2006394
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$275,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

956 Washington Avenue

Chestertown, MD

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View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
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$275,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

104 Acorn Drive

Chestertown, MD

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View 7482 Poplar Avenue Chestertown, MD MLS# MDKE2007042
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$275,000
3

Beds

1.0

Baths

975

Sq.Ft.

7482 Poplar Avenue

Chestertown, MD

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View 10540 Tonopah Road Chestertown, MD MLS# MDKE2006880
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$269,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

10540 Tonopah Road

Chestertown, MD

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View 121 Metcalf Road Chestertown, MD MLS# MDKE2006678
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$264,900
3

Beds

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Baths

121 Metcalf Road

Chestertown, MD

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View 115 Metcalf Road Chestertown, MD MLS# MDKE2006826
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$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

115 Metcalf Road

Chestertown, MD

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View 103 Metcalf Road Chestertown, MD MLS# MDKE2007148
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$259,900
3

Beds

2.1

Baths

1,280

Sq.Ft.

103 Metcalf Road

Chestertown, MD

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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

Price Count
$0 - 100K 34
$100K - 200K 6
$200K - 300K 18
$300K - 400K 20
$400K - 500K 10
$500K - 600K 1
$600K - 700K 5
$700K - 800K 10
$800K - 900K 7
$900K - 1M 0
$1M - Max 17

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 48
Townhouse 6
Condo 16
Commercial 12
Rental 9
Lots and Land 45
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 1

(Data as of 10/2/2026)

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