View 22481 Goose Hollow Drive Chestertown, MD MLS# MDKE2006682
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$279,900
3

Beds

2.0

Baths

1,296

Sq.Ft.

22481 Goose Hollow Drive

Chestertown, MD

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Courtesy of KELLER WILLIAMS LEGACY
View 104 Conley Drive Chestertown, MD MLS# MDKE2006686
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$247,000
3

Beds

1.1

Baths

1,280

Sq.Ft.

104 Conley Drive

Chestertown, MD

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Courtesy of CUMMINGS & CO. REALTORS
View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
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$284,900
3

Beds

2.1

Baths

1,900

Sq.Ft.

104 Acorn Drive

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 234 N College Avenue Chestertown, MD MLS# MDKE2006670
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$100,000
2

Beds

1.0

Baths

1,296

Sq.Ft.

234 N College Avenue

Chestertown, MD

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

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Fairlee Road

Chestertown, MD

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Courtesy of RE/MAX CHESAPEAKE
View 23264 Clarissa Road Chestertown, MD MLS# MDKE2006096
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$365,000
3

Beds

2.0

Baths

1,248

Sq.Ft.

23264 Clarissa Road

Chestertown, MD

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Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 110 Prospect Street Chestertown, MD MLS# MDKE2006626
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$119,895
3

Beds

1.1

Baths

2,210

Sq.Ft.

110 Prospect Street

Chestertown, MD

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Courtesy of ANR REALTY, LLC
View 8886 Georgetown Road Chestertown, MD MLS# MDKE2006634
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$80,000
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0.0

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8886 Georgetown Road

Chestertown, MD

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Courtesy of SAMSON PROPERTIES
View 21172 Wyoming Avenue Chestertown, MD MLS# MDKE2006642
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$200,000
4

Beds

1.0

Baths

2,920

Sq.Ft.

21172 Wyoming Avenue

Chestertown, MD

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Courtesy of BLUE STAR REAL ESTATE, LLC
View 10572 Watonga Road Chestertown, MD MLS# MDKE2006644
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$325,000
3

Beds

2.0

Baths

1,404

Sq.Ft.

10572 Watonga Road

Chestertown, MD

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Courtesy of SERHANT
View 213 Byford Drive Chestertown, MD MLS# MDKE2006026
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$380,000
4

Beds

2.0

Baths

1,277

Sq.Ft.

213 Byford Drive

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 522 High Street Chestertown, MD MLS# MDKE2006614
Save 522 High Street Chestertown, MD MLS# MDKE2006614
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$425,000
2

Beds

3.0

Baths

1,518

Sq.Ft.

522 High Street

Chestertown, MD

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Courtesy of BENSON & MANGOLD, LLC
View 23741 L Road Chestertown, MD MLS# MDKE2006622
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$15,000
Studio

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0.0

Baths

23741 L Road

Chestertown, MD

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Courtesy of BENSON & MANGOLD, LLC
View 956 Washington Avenue Chestertown, MD MLS# MDKE2006394
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$285,000
3

Beds

1.0

Baths

1,248

Sq.Ft.

956 Washington Avenue

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2006592
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$55,000
Studio

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0.0

Baths

Map 36 Parcel 80 Watertower Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 102 Flying Cloud Drive Chestertown, MD MLS# MDKE2006586
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$329,900
3

Beds

2.1

Baths

1,896

Sq.Ft.

102 Flying Cloud Drive

Chestertown, MD

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Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 423 Calvert Street Chestertown, MD MLS# MDKE2006578
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$185,000
3

Beds

1.1

Baths

1,136

Sq.Ft.

423 Calvert Street

Chestertown, MD

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Courtesy of COMPASS
View 23683 L Road Chestertown, MD MLS# MDKE2006580
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$6,000
Studio

Beds

0.0

Baths

23683 L Road

Chestertown, MD

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Courtesy of ALEX COOPER AUCTIONEERS, INC.
View 21363 Lynn Lane Chestertown, MD MLS# MDKE2006556
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$205,000
3

Beds

1.0

Baths

1,314

Sq.Ft.

21363 Lynn Lane

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 304 Hadaway Drive Chestertown, MD MLS# MDKE2006482
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$314,900
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

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Courtesy of REDFIN CORPORATION

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

127

Estimated median home price

$350,000
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 32
$100K - 200K 10
$200K - 300K 15
$300K - 400K 17
$400K - 500K 13
$500K - 600K 5
$600K - 700K 4
$700K - 800K 8
$800K - 900K 6
$900K - 1M 0
$1M - Max 17

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 54
Townhouse 7
Condo 16
Commercial 10
Rental 14
Lots and Land 40
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 6/20/2026)

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