View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
  • Recently Listed with Virtual Tour
1 of 40
$598,000
5

Beds

3.1

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 21111 Texas Avenue Chestertown, MD MLS# MDKE2005932
$370,000
3

Beds

2.0

Baths

1,680

Sq.Ft.

21111 Texas Avenue

Chestertown, MD

Bright
Courtesy of KELLER WILLIAMS SELECT REALTORS OF EASTON
View 108 Flying Cloud Drive Chestertown, MD MLS# MDKE2005928
  • Recently Listed
1 of 21
$375,000
4

Beds

2.1

Baths

1,936

Sq.Ft.

108 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View Georgetown Road Chestertown, MD MLS# MDKE2005844
  • Recently Listed
1 of 7
$89,500
Studio

Beds

0.0

Baths

Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 7521 Pine Avenue Chestertown, MD MLS# MDKE2005920
  • Recently Listed
1 of 24
OPEN HOUSE: Saturday 12/6 12:00 PM - 1:00 PM
$265,000
3

Beds

1.0

Baths

1,040

Sq.Ft.

7521 Pine Avenue

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 108 Little Harbor Way Chestertown, MD MLS# MDKE2005902
$635,000
Studio

Beds

0.0

Baths

108 Little Harbor Way

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
$299,000
2

Beds

1.1

Baths

920

Sq.Ft.

611 Cannon Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 204 Rolling Road Chestertown, MD MLS# MDKE2005896
$370,000
3

Beds

2.0

Baths

2,296

Sq.Ft.

204 Rolling Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 101 Metcalf Road Chestertown, MD MLS# MDKE2005882
  • New Construction
1 of 26
$264,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

101 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 112 Silver Heel Drive Chestertown, MD MLS# MDKE2005880
$369,900
5

Beds

3.1

Baths

2,615

Sq.Ft.

112 Silver Heel Drive

Chestertown, MD

Bright
Courtesy of EXP REALTY, LLC
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
1 of 30
OPEN HOUSE: Sunday 12/7 10:00 AM - 12:00 PM
$470,000
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 304 Hadaway Drive Chestertown, MD MLS# MDKE2005848
$399,000
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
  • Virtual Tour
1 of 53
$499,900
4

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 109 S College Avenue Chestertown, MD MLS# MDKE2005818
$449,900
3

Beds

2.1

Baths

1,216

Sq.Ft.

109 S College Avenue

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 303 E Campus Avenue Chestertown, MD MLS# MDKE2005756
$363,000
3

Beds

2.0

Baths

1,532

Sq.Ft.

303 E Campus Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 206 S Water Street Chestertown, MD MLS# MDKE2005840
$619,000
4

Beds

3.1

Baths

2,008

Sq.Ft.

206 S Water Street

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View 318 Lincoln Chestertown, MD MLS# MDKE2005842
$269,000
3

Beds

2.0

Baths

960

Sq.Ft.

318 Lincoln

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8750 Georgetown Road Chestertown, MD MLS# MDKE2005834
$339,000
3

Beds

2.0

Baths

1,900

Sq.Ft.

8750 Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824
$419,000
3

Beds

2.1

Baths

1,676

Sq.Ft.

411 Greenwood Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 101 Birch Run Road Chestertown, MD MLS# MDKE2005810
$499,999
3

Beds

2.0

Baths

1,961

Sq.Ft.

101 Birch Run Road

Chestertown, MD

Bright
Courtesy of REMAX VISION

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

$320,000
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 37
$100K - 200K 10
$200K - 300K 11
$300K - 400K 14
$400K - 500K 11
$500K - 600K 5
$600K - 700K 8
$700K - 800K 4
$800K - 900K 6
$900K - 1M 0
$1M - Max 14

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 49
Townhouse 9
Condo 9
Commercial 6
Rental 4
Lots and Land 44
Condo/Town/CoOp 0
CoOp 0
Multi Family 2
Mobile Home 0
Farms 1

(Data as of 11/11/2025)

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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