View 21146 Montana Avenue Chestertown, MD MLS# MDKE2006858
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$289,900
2

Beds

1.1

Baths

1,500

Sq.Ft.

21146 Montana Avenue

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
View 8312 Broad Neck Road Chestertown, MD MLS# MDKE2006854
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$380,000
3

Beds

1.1

Baths

3,292

Sq.Ft.

8312 Broad Neck Road

Chestertown, MD

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Courtesy of PEARSON SMITH REALTY, LLC
View 201 N Lynchburg Street Chestertown, MD MLS# MDKE2006844
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$500,000
2,045

Sq.Ft.

201 N Lynchburg Street

Chestertown, MD

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Courtesy of RE/MAX ASSOCIATES-HOCKESSIN
The time to sell is now! THE TIME TO SELL IS NOW!
View 201 N Lynchburg Street # LOTS 4, 5, 6 & 7 Chestertown, MD MLS# MDKE2006846
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$300,000
Studio

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0.0

Baths

201 N Lynchburg Street # LOTS 4, 5, 6 & 7

Chestertown, MD

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Courtesy of RE/MAX ASSOCIATES-HOCKESSIN
View 115 Metcalf Road Chestertown, MD MLS# MDKE2006826
  • New Construction
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OPEN HOUSE: Thursday 8/27 5:00 PM - 7:00 PM
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

115 Metcalf Road

Chestertown, MD

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Courtesy of REAL BROKER, LLC - CHESTER
View 200 Manor Avenue Chestertown, MD MLS# MDKE2006808
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$325,000
4

Beds

2.0

Baths

2,198

Sq.Ft.

200 Manor Avenue

Chestertown, MD

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Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 121 Metcalf Road Chestertown, MD MLS# MDKE2006678
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$264,900
3

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1.1

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121 Metcalf Road

Chestertown, MD

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Courtesy of REAL BROKER, LLC - CHESTER
View 21324 Persimmon Drive Chestertown, MD MLS# MDKE2006816
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$189,000
2

Beds

1.0

Baths

1,232

Sq.Ft.

21324 Persimmon Drive

Chestertown, MD

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Courtesy of BENSON & MANGOLD, LLC
View 10720 Foreston Road Chestertown, MD MLS# MDKE2006800
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$309,000
3

Beds

2.0

Baths

1,412

Sq.Ft.

10720 Foreston Road

Chestertown, MD

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View 409 Calvert Street Chestertown, MD MLS# MDKE2006794
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$145,000
3

Beds

1.1

Baths

1,192

Sq.Ft.

409 Calvert Street

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 9126 Fairlee Road Chestertown, MD MLS# MDKE2006764
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$324,000
3

Beds

1.1

Baths

1,216

Sq.Ft.

9126 Fairlee Road

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 896 Washington Avenue Chestertown, MD MLS# MDKE2006750
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$325,000
3

Beds

1.0

Baths

1,000

Sq.Ft.

896 Washington Avenue

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 105 N Water Street # 2 Chestertown, MD MLS# MDKE2006680
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$475,000
2

Beds

2.0

Baths

1,011

Sq.Ft.

105 N Water Street # 2

Chestertown, MD

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View 104 Conley Drive Chestertown, MD MLS# MDKE2006686
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$239,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

104 Conley Drive

Chestertown, MD

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Courtesy of CUMMINGS & CO. REALTORS
View 25750 Collins Avenue Chestertown, MD MLS# MDKE2006546
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$448,000
3

Beds

2.0

Baths

3,262

Sq.Ft.

25750 Collins Avenue

Chestertown, MD

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View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
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$275,000
3

Beds

2.1

Baths

1,900

Sq.Ft.

104 Acorn Drive

Chestertown, MD

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View 234 N College Avenue Chestertown, MD MLS# MDKE2006670
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$85,000
2

Beds

1.0

Baths

1,296

Sq.Ft.

234 N College Avenue

Chestertown, MD

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View Fairlee Road Chestertown, MD MLS# MDKE2006672
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$75,000
Studio

Beds

0.0

Baths

Fairlee Road

Chestertown, MD

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View 101 S Mill Street Chestertown, MD MLS# MDKE2006674
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$515,000
2

Beds

2.1

Baths

1,476

Sq.Ft.

101 S Mill Street

Chestertown, MD

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View 8886 Georgetown Road Chestertown, MD MLS# MDKE2006634
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$69,900
Studio

Beds

0.0

Baths

8886 Georgetown Road

Chestertown, MD

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Courtesy of SAMSON PROPERTIES

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

130

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 33
$100K - 200K 7
$200K - 300K 20
$300K - 400K 19
$400K - 500K 13
$500K - 600K 3
$600K - 700K 5
$700K - 800K 12
$800K - 900K 7
$900K - 1M 0
$1M - Max 11

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 47
Townhouse 12
Condo 17
Commercial 11
Rental 11
Lots and Land 43
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 8/25/2026)

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