View 22470 Fairgale Farm Lane Chestertown, MD MLS# MDKE2006502
$1,450,000
4

Beds

5.0

Baths

4,257

Sq.Ft.

22470 Fairgale Farm Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 102 Flying Cloud Drive Chestertown, MD MLS# MDKE2006586
$329,900
3

Beds

2.1

Baths

1,896

Sq.Ft.

102 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 304 Hadaway Drive Chestertown, MD MLS# MDKE2006482
  • Virtual Tour
1 of 38
$309,900
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of REDFIN CORPORATION
The time to sell is now! THE TIME TO SELL IS NOW!
View Sandy Bottom Road Chestertown, MD MLS# MDKE2006554
$59,000
Studio

Beds

0.0

Baths

Sandy Bottom Road

Chestertown, MD

Bright
Courtesy of VILLAGE REAL ESTATE COMPANY LLC
View 107 Flying Cloud Drive Chestertown, MD MLS# MDKE2006510
$375,000
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
$340,000
4

Beds

2.1

Baths

1,972

Sq.Ft.

214 Silver Heel Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 407 High Street Chestertown, MD MLS# MDKE2006496
$798,000
3

Beds

4.1

Baths

3,047

Sq.Ft.

407 High Street

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
$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 - CHESTER
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 226 S Water Street Chestertown, MD MLS# MDKE2006354
1 of 32
OPEN HOUSE: Saturday 8/1 11:00 AM - 1:00 PM
$898,000
3

Beds

3.1

Baths

2,172

Sq.Ft.

226 S Water Street

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 327 Cannon Street Chestertown, MD MLS# MDKE2006104
$1,300,000
3,518

Sq.Ft.

327 Cannon Street

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 103 Sutton Way Chestertown, MD MLS# MDKE2006344
  • Virtual Tour
1 of 53
$550,000
5

Beds

3.1

Baths

3,816

Sq.Ft.

103 Sutton Way

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View Cogar Road Chestertown, MD MLS# MDKE2006304
$3,000
Studio

Beds

0.0

Baths

Cogar Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View 139 Prospect Street Chestertown, MD MLS# MDKE2006250
$198,000
3

Beds

1.0

Baths

1,200

Sq.Ft.

139 Prospect Street

Chestertown, MD

Bright
Courtesy of REDFIN CORP
View Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006274
$225,000
Studio

Beds

0.0

Baths

Haacke Drive Lot 3

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006290
$250,000
Studio

Beds

0.0

Baths

Scheeler Road Lot 2

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View Scheeler Road Lot 2 Chestertown, MD MLS# MDKE2006298
  • New Construction
1 of 4
$250,000
37,026

Sq.Ft.

Scheeler Road Lot 2

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View Haacke Drive Lot 3 Chestertown, MD MLS# MDKE2006302
  • New Construction
1 of 4
$225,000

Haacke Drive Lot 3

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, 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

$325,000
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 32
$100K - 200K 8
$200K - 300K 16
$300K - 400K 17
$400K - 500K 8
$500K - 600K 3
$600K - 700K 4
$700K - 800K 11
$800K - 900K 7
$900K - 1M 0
$1M - Max 15

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 44
Townhouse 10
Condo 17
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 7/25/2026)

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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