View 21324 Persimmon Drive Chestertown, MD MLS# MDKE2006816
$199,000
2

Beds

1.0

Baths

1,232

Sq.Ft.

21324 Persimmon Drive

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 10720 Foreston Road Chestertown, MD MLS# MDKE2006800
  • Recently Listed
1 of 42
$335,000
3

Beds

2.0

Baths

1,412

Sq.Ft.

10720 Foreston Road

Chestertown, MD

Bright
Courtesy of COMPASS
View 109 Cedar Street Chestertown, MD MLS# MDKE2006792
  • Virtual Tour
1 of 22
$325,000
3

Beds

1.2

Baths

1,397

Sq.Ft.

109 Cedar Street

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 409 Calvert Street Chestertown, MD MLS# MDKE2006794
  • Recently Listed
1 of 9
$155,000
3

Beds

1.1

Baths

1,192

Sq.Ft.

409 Calvert Street

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 521 N Kent Street Chestertown, MD MLS# MDKE2006784
$385,000
3

Beds

2.0

Baths

1,934

Sq.Ft.

521 N Kent Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 9126 Fairlee Road Chestertown, MD MLS# MDKE2006764
  • Recently Listed
1 of 20
$344,000
3

Beds

1.1

Baths

1,216

Sq.Ft.

9126 Fairlee Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 896 Washington Avenue Chestertown, MD MLS# MDKE2006750
  • Recently Listed
1 of 34
$325,000
3

Beds

1.0

Baths

1,000

Sq.Ft.

896 Washington Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 105 N Water Street # 2 Chestertown, MD MLS# MDKE2006680
  • Recently Listed with Virtual Tour
1 of 49
$475,000
2

Beds

2.0

Baths

1,011

Sq.Ft.

105 N Water Street # 2

Chestertown, MD

Bright
Courtesy of NORTHROP REALTY
View 22481 Goose Hollow Drive Chestertown, MD MLS# MDKE2006682
$279,900
3

Beds

2.0

Baths

1,296

Sq.Ft.

22481 Goose Hollow Drive

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS LEGACY
View 104 Conley Drive Chestertown, MD MLS# MDKE2006686
$239,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

104 Conley Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 25750 Collins Avenue Chestertown, MD MLS# MDKE2006546
$468,000
3

Beds

2.0

Baths

3,262

Sq.Ft.

25750 Collins Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 104 Acorn Drive Chestertown, MD MLS# MDKE2006668
$284,900
3

Beds

2.1

Baths

1,900

Sq.Ft.

104 Acorn Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 234 N College Avenue Chestertown, MD MLS# MDKE2006670
$90,000
2

Beds

1.0

Baths

1,296

Sq.Ft.

234 N College Avenue

Chestertown, MD

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

Beds

0.0

Baths

Fairlee Road

Chestertown, MD

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

Beds

2.0

Baths

1,248

Sq.Ft.

23264 Clarissa Road

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 101 S Mill Street Chestertown, MD MLS# MDKE2006674
  • Virtual Tour
1 of 39
$515,000
2

Beds

2.1

Baths

1,476

Sq.Ft.

101 S Mill Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 110 Prospect Street Chestertown, MD MLS# MDKE2006626
$79,900
3

Beds

1.1

Baths

2,210

Sq.Ft.

110 Prospect Street

Chestertown, MD

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

Beds

0.0

Baths

8886 Georgetown Road

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View 10781 Fermoy Road Chestertown, MD MLS# MDKE2006640
$429,900
4

Beds

2.1

Baths

2,160

Sq.Ft.

10781 Fermoy Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 21172 Wyoming Avenue Chestertown, MD MLS# MDKE2006642
$200,000
4

Beds

1.0

Baths

2,920

Sq.Ft.

21172 Wyoming Avenue

Chestertown, MD

Bright
Courtesy of BLUE STAR REAL ESTATE, LLC

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

$332,450
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 9
$200K - 300K 13
$300K - 400K 19
$400K - 500K 8
$500K - 600K 4
$600K - 700K 4
$700K - 800K 10
$800K - 900K 6
$900K - 1M 0
$1M - Max 15

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 47
Townhouse 7
Condo 17
Commercial 10
Rental 14
Lots and Land 39
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 7/11/2026)

Information deemed reliable but not guaranteed.

Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BrightMLS Broker ReciprocitySM program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Weichert, Realtors® participates, and is provided by BrightMLS through a licensing agreement.

Real estate listings held by brokerage firms other than Weichert, Realtors® are marked with the Broker Reciprocity icon (a little black house) and detailed information about each listing includes the name of the listing broker.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale.

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