View 304 Hadaway Drive Chestertown, MD MLS# MDKE2006482
  • Recently Listed with Virtual Tour
1 of 38
$329,900
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of REDFIN CORPORATION
View Sandy Bottom Road Chestertown, MD MLS# MDKE2006554
  • Recently Listed
1 of 6
$79,000
Studio

Beds

0.0

Baths

Sandy Bottom Road

Chestertown, MD

Bright
Courtesy of VILLAGE REAL ESTATE COMPANY LLC
View 202 Valley Road Chestertown, MD MLS# MDKE2006538
$325,000
3

Beds

1.0

Baths

1,427

Sq.Ft.

202 Valley Road

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 100 Prospect Street Chestertown, MD MLS# MDKE2006544
$215,000
3

Beds

1.0

Baths

1,373

Sq.Ft.

100 Prospect Street

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 8629 Airy Hill Road Chestertown, MD MLS# MDKE2006526
$425,000
3

Beds

2.0

Baths

1,440

Sq.Ft.

8629 Airy Hill Road

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS REALTY
View 107 Flying Cloud Drive Chestertown, MD MLS# MDKE2006510
$395,000
5

Beds

3.1

Baths

2,534

Sq.Ft.

107 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 214 Silver Heel Road Chestertown, MD MLS# MDKE2006498
  • Recently Listed
1 of 26
$350,000
4

Beds

2.1

Baths

1,972

Sq.Ft.

214 Silver Heel Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 144 Prospect Street Chestertown, MD MLS# MDKE2006494
  • Recently Listed
1 of 18
$179,000
2

Beds

1.1

Baths

1,082

Sq.Ft.

144 Prospect Street

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 23416 Cloquet Road Chestertown, MD MLS# MDKE2006486
$384,000
3

Beds

2.0

Baths

1,512

Sq.Ft.

23416 Cloquet Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 24581 Willow Oak Lane Chestertown, MD MLS# MDKE2006342
$229,990
3

Beds

2.0

Baths

1,352

Sq.Ft.

24581 Willow Oak Lane

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 116 Cross Street Chestertown, MD MLS# MDKE2006420
  • Recently Listed
1 of 9
$109,999
Studio

Beds

0.0

Baths

116 Cross Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 103 Metcalf Rd Chestertown, MD MLS# MDKE2006446
  • New Construction
1 of 22
$259,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

103 Metcalf Rd

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 103 Trafford Drive Chestertown, MD MLS# MDKE2006416
$419,900
3

Beds

2.1

Baths

1,944

Sq.Ft.

103 Trafford Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 108 Oak Leaf Drive Chestertown, MD MLS# MDKE2006224
$299,500
2

Beds

2.1

Baths

1,867

Sq.Ft.

108 Oak Leaf Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 8706 Elm Road Chestertown, MD MLS# MDKE2006390
$320,000
3

Beds

2.0

Baths

1,232

Sq.Ft.

8706 Elm Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
$445,000
2

Beds

2.1

Baths

1,857

Sq.Ft.

24295 Langford Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 10594 Millbrook Drive Chestertown, MD MLS# MDKE2006378
$329,000
3

Beds

2.0

Baths

1,499

Sq.Ft.

10594 Millbrook Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 115 Acorn Drive Chestertown, MD MLS# MDKE2006360
  • Virtual Tour
1 of 40
$296,000
2

Beds

2.1

Baths

1,864

Sq.Ft.

115 Acorn Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 21217 Texas Avenue Chestertown, MD MLS# MDKE2006364
$244,500
2

Beds

1.0

Baths

912

Sq.Ft.

21217 Texas Avenue

Chestertown, MD

Bright
Courtesy of RE/MAX LEADING EDGE
View 108 Pine Street Chestertown, MD MLS# MDKE2006322
$115,000
3

Beds

1.0

Baths

910

Sq.Ft.

108 Pine Street

Chestertown, MD

Bright
Courtesy of REAL BROKER, 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

121

Estimated median home price

$340,000
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 28
$100K - 200K 10
$200K - 300K 16
$300K - 400K 18
$400K - 500K 11
$500K - 600K 7
$600K - 700K 5
$700K - 800K 7
$800K - 900K 8
$900K - 1M 0
$1M - Max 11

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 50
Townhouse 8
Condo 17
Commercial 8
Rental 10
Lots and Land 37
Condo/Town/CoOp 0
CoOp 0
Multi Family 1
Mobile Home 0
Farms 0

(Data as of 5/14/2026)

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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