View 8796 Maryland Parkway Chestertown, MD MLS# MDKE2006632
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$1,650,000
5,000

Sq.Ft.

8796 Maryland Parkway

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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
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$450,000
2

Beds

3.0

Baths

1,518

Sq.Ft.

522 High Street

Chestertown, MD

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Courtesy of BENSON & MANGOLD, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 23741 L Road Chestertown, MD MLS# MDKE2006622
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$15,000
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23741 L Road

Chestertown, MD

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Courtesy of BENSON & MANGOLD, LLC
View 8796 Maryland Parkway Chestertown, MD MLS# MDKE2006596
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$1,650,000
9

Beds

6.1

Baths

4,776

Sq.Ft.

8796 Maryland Parkway

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
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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View 7761 Broad Neck Road Chestertown, MD MLS# MDKE2006542
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$1,500,000
5

Beds

2.1

Baths

2,700

Sq.Ft.

7761 Broad Neck Road

Chestertown, MD

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Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 25440 Learman Road Chestertown, MD MLS# MDKE2006468
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$3,000,000
3

Beds

2.2

Baths

3,142

Sq.Ft.

25440 Learman Road

Chestertown, MD

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View Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2006592
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$55,000
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Map 36 Parcel 80 Watertower Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 22470 Fairgale Farm Lane Chestertown, MD MLS# MDKE2006502
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$1,450,000
4

Beds

5.0

Baths

4,257

Sq.Ft.

22470 Fairgale Farm Lane

Chestertown, MD

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Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 102 Flying Cloud Drive Chestertown, MD MLS# MDKE2006586
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$339,900
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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View 23683 L Road Chestertown, MD MLS# MDKE2006580
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$6,000
Studio

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0.0

Baths

23683 L Road

Chestertown, MD

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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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$322,500
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

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View Sandy Bottom Road Chestertown, MD MLS# MDKE2006554
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$79,000
Studio

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0.0

Baths

Sandy Bottom Road

Chestertown, MD

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View 202 Valley Road Chestertown, MD MLS# MDKE2006538
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$325,000
3

Beds

1.0

Baths

1,427

Sq.Ft.

202 Valley Road

Chestertown, MD

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View 100 Prospect Street Chestertown, MD MLS# MDKE2006544
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$215,000
3

Beds

1.0

Baths

1,373

Sq.Ft.

100 Prospect Street

Chestertown, MD

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View 110 S Queen Street Chestertown, MD MLS# MDKE2006536
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$525,000
1,785

Sq.Ft.

110 S Queen Street

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
View 8629 Airy Hill Road Chestertown, MD MLS# MDKE2006526
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$425,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

8629 Airy Hill Road

Chestertown, MD

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Courtesy of KELLER WILLIAMS REALTY

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

120

Estimated median home price

$339,950
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 30
$100K - 200K 8
$200K - 300K 15
$300K - 400K 16
$400K - 500K 12
$500K - 600K 5
$600K - 700K 4
$700K - 800K 7
$800K - 900K 7
$900K - 1M 0
$1M - Max 16

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 51
Townhouse 5
Condo 17
Commercial 8
Rental 13
Lots and Land 39
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 6/3/2026)

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