View 300 and 302 S Mill Street Chestertown, MD MLS# MDKE2006850
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$1,195,000
2

Beds

1.0

Baths

806

Sq.Ft.

300 and 302 S Mill Street

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8184 Rock Hall Road Chestertown, MD MLS# MDKE2007006
Save 8184 Rock Hall Road Chestertown, MD MLS# MDKE2007006
1 of 38
$38,200,000
4

Beds

2.0

Baths

2,330

Sq.Ft.

8184 Rock Hall Road

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
View 23208 Buck Neck Road Chestertown, MD MLS# MDKE2006980
  • New Construction
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$349,900
3

Beds

2.1

Baths

1,650

Sq.Ft.

23208 Buck Neck Road

Chestertown, MD

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Courtesy of REAL BROKER, LLC - CHESTER
The time to sell is now! THE TIME TO SELL IS NOW!
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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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 123 Trafford Drive Chestertown, MD MLS# MDKE2006970
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1 of 45
$370,000
4

Beds

2.1

Baths

2,504

Sq.Ft.

123 Trafford Drive

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 1003 Twin Court Chestertown, MD MLS# MDKE2006974
Save 1003 Twin Court Chestertown, MD MLS# MDKE2006974
1 of 48
$499,900
3

Beds

2.1

Baths

2,076

Sq.Ft.

1003 Twin Court

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
View 115 Chester Arms Drive Chestertown, MD MLS# MDKE2006958
Save 115 Chester Arms Drive Chestertown, MD MLS# MDKE2006958
1 of 34
$259,000
3

Beds

2.0

Baths

1,140

Sq.Ft.

115 Chester Arms Drive

Chestertown, MD

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Courtesy of SAMSON PROPERTIES
View 101 S College Avenue Chestertown, MD MLS# MDKE2006918
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1 of 35
$359,000
2

Beds

1.1

Baths

1,036

Sq.Ft.

101 S College Avenue

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 7982 Radcliffe Road Chestertown, MD MLS# MDKE2006950
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$399,000
2

Beds

2.0

Baths

1,904

Sq.Ft.

7982 Radcliffe Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View Cannon Street Chestertown, MD MLS# MDKE2006940
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1 of 9
$196,000
0.0

Baths

Cannon Street

Chestertown, MD

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Courtesy of TAYLOR PROPERTIES
View Cannon Street Chestertown, MD MLS# MDKE2006944
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1 of 9
$281,000
0.0

Baths

Cannon Street

Chestertown, MD

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Courtesy of TAYLOR PROPERTIES
View 216 Birch Run Road Chestertown, MD MLS# MDKE2006896
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$750,000
3

Beds

2.1

Baths

2,176

Sq.Ft.

216 Birch Run Road

Chestertown, MD

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Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 620 Cannon Street Chestertown, MD MLS# MDKE2006922
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$85,000
0.0

Baths

620 Cannon Street

Chestertown, MD

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View 8630 Elm Road Chestertown, MD MLS# MDKE2006914
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1 of 55
$424,900
5

Beds

2.1

Baths

1,936

Sq.Ft.

8630 Elm Road

Chestertown, MD

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Courtesy of SAVE 6, INCORPORATED
View Sandpiper Road Chestertown, MD MLS# MDKE2006902
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$4,500
0.0

Baths

Sandpiper Road

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 129 Trafford Drive Chestertown, MD MLS# MDKE2006878
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$480,000
3

Beds

2.1

Baths

3,176

Sq.Ft.

129 Trafford Drive

Chestertown, MD

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Courtesy of ELEVATED REAL ESTATE SOLUTIONS
View 10540 Tonopah Road Chestertown, MD MLS# MDKE2006880
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1 of 21
$269,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

10540 Tonopah Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 1010 Twin Court Chestertown, MD MLS# MDKE2006874
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1 of 25
$349,900
4

Beds

2.0

Baths

1,476

Sq.Ft.

1010 Twin Court

Chestertown, MD

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Courtesy of KEVIN DEY REALTY
View 201 N Lynchburg Street Chestertown, MD MLS# MDKE2006844
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1 of 13
$500,000
2,045

Sq.Ft.

201 N Lynchburg Street

Chestertown, MD

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Courtesy of RE/MAX ASSOCIATES-HOCKESSIN
View 201 N Lynchburg Street # LOTS 4, 5, 6 & 7 Chestertown, MD MLS# MDKE2006846
Save 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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Courtesy of RE/MAX ASSOCIATES-HOCKESSIN

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

129

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 19
$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 50
Townhouse 6
Condo 15
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 9/30/2026)

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