View 8184 Rock Hall Road Chestertown, MD MLS# MDKE2007006
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$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 Cromwell Clark Road Chestertown, MD MLS# MDKE2005156
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$3,000,000
0.0

Baths

Cromwell Clark Road

Chestertown, MD

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Courtesy of THE LAND GROUP
View 6324 Quaker Neck Road Chestertown, MD MLS# MDKE2007098
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$2,895,000
5

Beds

3.1

Baths

5,938

Sq.Ft.

6324 Quaker Neck Road

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 200-204 High Street Chestertown, MD MLS# MDKE2006810
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1 of 58
$2,300,000
6,918

Sq.Ft.

200-204 High Street

Chestertown, MD

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Courtesy of TAYLOR PROPERTIES
View 117 Water Street N # 1A, 1B, 2A, & 2B Chestertown, MD MLS# MDKE2006158
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$1,500,000
7

Beds

5.0

Baths

5,400

Sq.Ft.

117 Water Street N # 1A, 1B, 2A, & 2B

Chestertown, MD

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Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 8796 Maryland Parkway Chestertown, MD MLS# MDKE2006596
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$1,495,000
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 8796 Maryland Parkway Chestertown, MD MLS# MDKE2006632
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$1,495,000
5,000

Sq.Ft.

8796 Maryland Parkway

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Little Harbor Way # 1 Chestertown, MD MLS# MDKE2005768
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$1,459,000
3

Beds

2.1

Baths

2,231

Sq.Ft.

Little Harbor Way # 1

Chestertown, MD

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Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 22470 Fairgale Farm Lane Chestertown, MD MLS# MDKE2006502
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$1,375,000
4

Beds

5.0

Baths

4,257

Sq.Ft.

22470 Fairgale Farm Lane

Chestertown, MD

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View 327 Cannon Street Chestertown, MD MLS# MDKE2006104
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$1,300,000
3,518

Sq.Ft.

327 Cannon Street

Chestertown, MD

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Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 8276 Broad Neck Road Chestertown, MD MLS# MDKE2007092
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$1,295,000
4

Beds

3.1

Baths

3,383

Sq.Ft.

8276 Broad Neck Road

Chestertown, MD

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Courtesy of SELECT LAND & HOMES, LLC
View 105 High Street Chestertown, MD MLS# MDKE2005890
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OPEN HOUSE: Saturday 10/3 10:00 AM - 12:00 PM
$1,245,500
5

Beds

4.1

Baths

3,243

Sq.Ft.

105 High Street

Chestertown, MD

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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 300 and 302 S Mill Street Chestertown, MD MLS# MDKE2007020
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$1,195,000
0.0

Baths

300 and 302 S Mill Street

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 25416 Commerce Lane Chestertown, MD MLS# MDKE2006664
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$1,100,000
5,600

Sq.Ft.

25416 Commerce Lane

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View #25 Landing Lane Chestertown, MD MLS# MDKE2005954
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$1,099,900
4

Beds

3.1

Baths

2,784

Sq.Ft.

#25 Landing Lane

Chestertown, MD

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View 104 Maple Avenue Chestertown, MD MLS# MDKE2007096
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$1,050,000
7,296

Sq.Ft.

104 Maple Avenue

Chestertown, MD

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Courtesy of REAL BROKER, LLC - ANNAPOLIS
View 226 S Water Street Chestertown, MD MLS# MDKE2006354
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$898,000
3

Beds

3.1

Baths

2,172

Sq.Ft.

226 S Water Street

Chestertown, MD

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View 104 Little Harbor Way Chestertown, MD MLS# MDKE2005894
  • New Construction
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$849,900
3

Beds

2.1

Baths

1,980

Sq.Ft.

104 Little Harbor Way

Chestertown, MD

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Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 102 Little Harbor Way Chestertown, MD MLS# MDKE2005950
  • New Construction
Save 102 Little Harbor Way Chestertown, MD MLS# MDKE2005950
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$839,500
3

Beds

2.1

Baths

1,964

Sq.Ft.

102 Little Harbor Way

Chestertown, MD

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Courtesy of GUNTHER-MCCLARY REAL ESTATE

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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