View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
  • Virtual Tour
1 of 66
$499,900
4

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 1014 Twin Court Chestertown, MD MLS# MDKE2006516
$499,000
3

Beds

2.0

Baths

1,817

Sq.Ft.

1014 Twin Court

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
  • Virtual Tour
1 of 41
$475,000
4

Beds

3.0

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
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 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$450,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 10781 Fermoy Road Chestertown, MD MLS# MDKE2006640
  • Recently Listed
1 of 54
$449,900
4

Beds

2.1

Baths

2,160

Sq.Ft.

10781 Fermoy Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
$430,000
2

Beds

2.1

Baths

1,857

Sq.Ft.

24295 Langford Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
$429,999
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
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 522 High Street Chestertown, MD MLS# MDKE2006614
  • Recently Listed
1 of 15
$425,000
2

Beds

3.0

Baths

1,518

Sq.Ft.

522 High Street

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 109 S College Avenue Chestertown, MD MLS# MDKE2006040
$419,900
3

Beds

2.1

Baths

1,216

Sq.Ft.

109 S College Avenue

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 103 Trafford Drive Chestertown, MD MLS# MDKE2006416
1 of 67
OPEN HOUSE: Saturday 6/20 11:00 AM - 1:00 PM
$399,900
3

Beds

2.1

Baths

1,944

Sq.Ft.

103 Trafford Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 104 Flying Cloud Drive Chestertown, MD MLS# MDKE2006212
$394,900
5

Beds

3.1

Baths

2,535

Sq.Ft.

104 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 23043 Bay Shore Spur Chestertown, MD MLS# MDKE2005584
$385,000
4

Beds

3.0

Baths

2,630

Sq.Ft.

23043 Bay Shore Spur

Chestertown, MD

Bright
Courtesy of ROCK HALL PROPERTIES REAL ESTATE
View 107 Flying Cloud Drive Chestertown, MD MLS# MDKE2006510
$385,000
5

Beds

3.1

Baths

2,534

Sq.Ft.

107 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CENTURY 21 NEW MILLENNIUM
View 6746 Quaker Neck Road Chestertown, MD MLS# MDKE2006014
$384,000
5

Beds

2.1

Baths

3,371

Sq.Ft.

6746 Quaker Neck Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 6746 Quaker Road Chestertown, MD MLS# MDKE2006022
$384,000
3,371

Sq.Ft.

6746 Quaker Road

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 213 Byford Drive Chestertown, MD MLS# MDKE2006026
  • Recently Listed with Virtual Tour
1 of 39
$380,000
4

Beds

2.0

Baths

1,277

Sq.Ft.

213 Byford Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 117 Water Street N # 2A Chestertown, MD MLS# MDKE2006166
$375,000
2

Beds

1.0

Baths

787

Sq.Ft.

117 Water Street N # 2A

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY

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

129

Estimated median home price

$350,000
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 31
$100K - 200K 11
$200K - 300K 13
$300K - 400K 20
$400K - 500K 13
$500K - 600K 6
$600K - 700K 4
$700K - 800K 8
$800K - 900K 6
$900K - 1M 0
$1M - Max 17

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 57
Townhouse 6
Condo 16
Commercial 10
Rental 13
Lots and Land 40
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 0

(Data as of 6/16/2026)

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.

© 2026 BrightMLS. All Rights Reserved.