View 105 Sutton Way Chestertown, MD MLS# MDKE2003692
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$415,000
4

Beds

2.1

Baths

2,064

Sq.Ft.

105 Sutton Way

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 27370 Morgnec Road Chestertown, MD MLS# MDKE2003680
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$299,000
3

Beds

1.1

Baths

1,008

Sq.Ft.

27370 Morgnec Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View Cloquet Chestertown, MD MLS# MDKE2003654
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1 of 4
$70,000
Studio

Beds

0.0

Baths

Cloquet

Chestertown, MD

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Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 5772 Johnsontown Road Chestertown, MD MLS# MDKE2003668
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1 of 23
$350,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

5772 Johnsontown Road

Chestertown, MD

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Courtesy of CROSS STREET REALTORS LLC
View 24581 Willow Oak Lane Chestertown, MD MLS# MDKE2003640
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$149,000
2

Beds

2.0

Baths

1,352

Sq.Ft.

24581 Willow Oak Lane

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 9816 Fairlee Road Chestertown, MD MLS# MDKE2003632
Save 9816 Fairlee Road Chestertown, MD MLS# MDKE2003632
1 of 36
$520,000
3

Beds

3.0

Baths

1,624

Sq.Ft.

9816 Fairlee Road

Chestertown, MD

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Courtesy of RE/MAX EXECUTIVE
View 21357 Belair Chestertown, MD MLS# MDKE2003610
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1 of 27
$339,000
3

Beds

2.1

Baths

2,008

Sq.Ft.

21357 Belair

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2003624
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$55,000
Studio

Beds

0.0

Baths

Map 36 Parcel 80 Watertower Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 8757 Orchard Drive Chestertown, MD MLS# MDKE2003556
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Save 8757 Orchard Drive Chestertown, MD MLS# MDKE2003556
1 of 37
$529,000
2

Beds

2.1

Baths

2,210

Sq.Ft.

8757 Orchard Drive

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Elm Road Chestertown, MD MLS# MDKE2003590
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1 of 3
$20,000
Studio

Beds

0.0

Baths

Elm Road

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Lot 24 & 25 Buck Neck Road Chestertown, MD MLS# MDKE2003512
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$8,000
Studio

Beds

0.0

Baths

Lot 24 & 25 Buck Neck Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 106 Metcalf Road Chestertown, MD MLS# MDKE2003586
  • New Construction
Save 106 Metcalf Road Chestertown, MD MLS# MDKE2003586
1 of 18
$234,900
3

Beds

1.1

Baths

106 Metcalf Road

Chestertown, MD

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Courtesy of RE/MAX EXECUTIVE
View Millbrook Drive Chestertown, MD MLS# MDKE2003562
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$22,000
Studio

Beds

0.0

Baths

Millbrook Drive

Chestertown, MD

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Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 204 N Mill Street Chestertown, MD MLS# MDKE2003518
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1 of 44
$399,000
5

Beds

3.1

Baths

2,890

Sq.Ft.

204 N Mill Street

Chestertown, MD

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Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 23690 L Road Chestertown, MD MLS# MDKE2003424
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1 of 3
$25,000
Studio

Beds

0.0

Baths

23690 L Road

Chestertown, MD

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Courtesy of KELLER WILLIAMS FLAGSHIP OF MARYLAND
View 9020 Cumberland Street Chestertown, MD MLS# MDKE2003374
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1 of 48
$297,000
2

Beds

2.0

Baths

1,150

Sq.Ft.

9020 Cumberland Street

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Elm Road Chestertown, MD MLS# MDKE2003416
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1 of 1
$40,000
Studio

Beds

0.0

Baths

Elm Road

Chestertown, MD

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Courtesy of THE HOGANS AGENCY
View Montgomery Avenue Chestertown, MD MLS# MDKE2003418
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1 of 2
$40,000
Studio

Beds

0.0

Baths

Montgomery Avenue

Chestertown, MD

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Courtesy of THE HOGANS AGENCY
View Caulks Field Road Chestertown, MD MLS# MDKE2003398
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1 of 7
$30,000
Studio

Beds

0.0

Baths

Caulks Field Road

Chestertown, MD

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Courtesy of DOUG ASHLEY REALTORS, LLC
View 23683 L Road Chestertown, MD MLS# MDKE2003390
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1 of 3
$25,000
Studio

Beds

0.0

Baths

23683 L Road

Chestertown, MD

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Courtesy of THE LAND GROUP

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

87

Estimated median home price

$299,900
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 4
$200K - 300K 8
$300K - 400K 10
$400K - 500K 6
$500K - 600K 2
$600K - 700K 2
$700K - 800K 1
$800K - 900K 6
$900K - 1M 5
$1M - Max 11

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 31
Townhouse 8
Condo 5
Commercial 5
Rental 13
Lots and Land 34
Condo/Town/CoOp 0
CoOp 0
Multi Family 3
Mobile Home 0
Farms 1

(Data as of 4/23/2024)

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