View 144 Prospect Street Chestertown, MD MLS# MDKE2006494
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$179,000
2

Beds

1.1

Baths

1,082

Sq.Ft.

144 Prospect Street

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 9816 Fairlee Road Chestertown, MD MLS# MDKE2006488
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$535,000
3

Beds

3.0

Baths

1,624

Sq.Ft.

9816 Fairlee Road

Chestertown, MD

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Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 22360 Great Oak Landing Road Chestertown, MD MLS# MDKE2006478
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$525,000
5

Beds

3.1

Baths

2,688

Sq.Ft.

22360 Great Oak Landing Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 23416 Cloquet Road Chestertown, MD MLS# MDKE2006486
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$384,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

23416 Cloquet Road

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342
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$229,990
3

Beds

2.0

Baths

1,352

Sq.Ft.

24581 Willow Oak Lane

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 116 Cross Street Chestertown, MD MLS# MDKE2006420
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$109,999
Studio

Beds

0.0

Baths

116 Cross Street

Chestertown, MD

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Courtesy of SELECT LAND & HOMES, LLC
View 103 Metcalf Rd Chestertown, MD MLS# MDKE2006446
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$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

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View 103 Trafford Drive Chestertown, MD MLS# MDKE2006416
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$450,000
3

Beds

2.1

Baths

1,944

Sq.Ft.

103 Trafford Drive

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 108 Oak Leaf Drive Chestertown, MD MLS# MDKE2006224
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$299,500
2

Beds

2.1

Baths

1,867

Sq.Ft.

108 Oak Leaf Drive

Chestertown, MD

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View 8706 Elm Road Chestertown, MD MLS# MDKE2006390
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$320,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

8706 Elm Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
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$445,000
2

Beds

2.1

Baths

1,857

Sq.Ft.

24295 Langford Road

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 10594 Millbrook Drive Chestertown, MD MLS# MDKE2006378
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$329,000
3

Beds

2.0

Baths

1,499

Sq.Ft.

10594 Millbrook Drive

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 10087 John Carvill Road Chestertown, MD MLS# MDKE2006324
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$695,000
3

Beds

2.0

Baths

1,566

Sq.Ft.

10087 John Carvill Road

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 115 Acorn Drive Chestertown, MD MLS# MDKE2006360
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$296,000
2

Beds

2.1

Baths

1,864

Sq.Ft.

115 Acorn Drive

Chestertown, MD

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View 21217 Texas Avenue Chestertown, MD MLS# MDKE2006364
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$265,000
2

Beds

1.0

Baths

912

Sq.Ft.

21217 Texas Avenue

Chestertown, MD

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View 103 Sutton Way Chestertown, MD MLS# MDKE2006344
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$550,000
5

Beds

3.1

Baths

3,816

Sq.Ft.

103 Sutton Way

Chestertown, MD

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View 108 Pine Street Chestertown, MD MLS# MDKE2006322
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$115,000
3

Beds

1.0

Baths

910

Sq.Ft.

108 Pine Street

Chestertown, MD

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View 10584 Klamath Road Chestertown, MD MLS# MDKE2006328
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$319,900
3

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Baths

10584 Klamath Road

Chestertown, MD

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View 201 Birch Run Road Chestertown, MD MLS# MDKE2006316
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$435,000
3

Beds

2.0

Baths

1,588

Sq.Ft.

201 Birch Run Road

Chestertown, MD

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View Cogar Road Chestertown, MD MLS# MDKE2006304
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$3,000
Studio

Beds

0.0

Baths

Cogar 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

116

Estimated median home price

$334,450
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 29
$100K - 200K 10
$200K - 300K 15
$300K - 400K 15
$400K - 500K 9
$500K - 600K 7
$600K - 700K 5
$700K - 800K 7
$800K - 900K 7
$900K - 1M 0
$1M - Max 12

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 44
Townhouse 8
Condo 17
Commercial 8
Rental 11
Lots and Land 38
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 5/3/2026)

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