View 204 RICHARD DRIVE Chestertown, MD MLS# MDKE2003218
  • Recently Listed with Virtual Tour
1 of 54
$420,000
3

Beds

2.0

Baths

1,540

Sq.Ft.

204 RICHARD DRIVE

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 1006 TWIN COURT Chestertown, MD MLS# MDKE2003202
$385,000
3

Beds

2.1

Baths

1,800

Sq.Ft.

1006 TWIN COURT

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 104 METCALF ROAD Chestertown, MD MLS# MDKE2003198
  • Recently Listed
1 of 17
$234,900
3

Beds

1.1

Baths

104 METCALF ROAD

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
The time to sell is now! THE TIME TO SELL IS NOW!
View 8220 AIRY HILL ROAD Chestertown, MD MLS# MDKE2003162
  • Recently Listed
1 of 7
$499,000
0.0

Baths

8220 AIRY HILL ROAD

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 105-S WATER STREET Chestertown, MD MLS# MDKE2003176
$769,500
4

Beds

2.1

Baths

2,565

Sq.Ft.

105-S WATER STREET

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 410 CANNON STREET Chestertown, MD MLS# MDKE2003174
  • Recently Listed
1 of 23
$395,000
3

Beds

1.1

Baths

1,584

Sq.Ft.

410 CANNON STREET

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 110 CAMELOT DRIVE Chestertown, MD MLS# MDKE2003160
  • Price Reduced
1 of 69
$434,900
5

Beds

3.1

Baths

3,200

Sq.Ft.

110 CAMELOT DRIVE

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 6292 BROAD NECK ROAD Chestertown, MD MLS# MDKE2003156
$110,000
2

Beds

1.0

Baths

1,150

Sq.Ft.

6292 BROAD NECK ROAD

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 129 TRAFFORD DRIVE Chestertown, MD MLS# MDKE2003146
  • Price Reduced with Virtual Tour
1 of 49
$449,900
3

Beds

2.1

Baths

2,176

Sq.Ft.

129 TRAFFORD DRIVE

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 10761 KASOTA ROAD Chestertown, MD MLS# MDKE2003144
$875,000
3

Beds

3.0

Baths

2,382

Sq.Ft.

10761 KASOTA ROAD

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 23240 CLARISSA ROAD Chestertown, MD MLS# MDKE2003142
$299,500
3

Beds

2.0

Baths

1,404

Sq.Ft.

23240 CLARISSA ROAD

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 9762 VOGELER DRIVE Chestertown, MD MLS# MDKE2003100
$735,000
2

Beds

1.1

Baths

1,521

Sq.Ft.

9762 VOGELER DRIVE

Chestertown, MD

Bright
Courtesy of EXP REALTY, LLC
View 24349 CHESTERTOWN ROAD Chestertown, MD MLS# MDKE2003102
$299,950
3

Beds

1.0

Baths

1,327

Sq.Ft.

24349 CHESTERTOWN ROAD

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 411 GREENWOOD AVENUE Chestertown, MD MLS# MDKE2003132
$385,000
3

Beds

2.1

Baths

1,676

Sq.Ft.

411 GREENWOOD AVENUE

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 114 METCALF ROAD Chestertown, MD MLS# MDKE2003130
  • New Construction
1 of 17
$234,900
3

Beds

1.1

Baths

114 METCALF ROAD

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 209 E CAMPUS AVENUE Chestertown, MD MLS# MDKE2003128
$449,000
3

Beds

2.1

Baths

2,397

Sq.Ft.

209 E CAMPUS AVENUE

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 7920 CARRIAGE LANE Chestertown, MD MLS# MDKE2003114
$495,000
3

Beds

2.1

Baths

1,764

Sq.Ft.

7920 CARRIAGE LANE

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 23829 E FORK DRIVE Chestertown, MD MLS# MDKE2003096
$2,200,000
3

Beds

4.1

Baths

3,342

Sq.Ft.

23829 E FORK DRIVE

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 21217 TEXAS AVENUE Chestertown, MD MLS# MDKE2003120
$215,000
2

Beds

1.0

Baths

912

Sq.Ft.

21217 TEXAS AVENUE

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 100 SILVER HEEL DRIVE Chestertown, MD MLS# MDKE2003108
  • New Construction
1 of 42
$357,990
4

Beds

2.1

Baths

1,849

Sq.Ft.

100 SILVER HEEL DRIVE

Chestertown, MD

Bright
Courtesy of DRH REALTY CAPITAL, 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

68

Estimated median home price

$407,500
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 3
$100K - 200K 6
$200K - 300K 18
$300K - 400K 7
$400K - 500K 10
$500K - 600K 2
$600K - 700K 2
$700K - 800K 6
$800K - 900K 4
$900K - 1M 5
$1M - Max 5

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 38
Townhouse 15
Condo 0
Commercial 7
Rental 4
Lots and Land 8
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 10/3/2023)

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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