View 7655 James Lane Chestertown, MD MLS# MDKE2007208
  • Recently Listed
1 of 50
$519,900
3

Beds

2.1

Baths

2,475

Sq.Ft.

7655 James Lane

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 24607 Chestertown Road Chestertown, MD MLS# MDKE2007204
  • Recently Listed
1 of 28
$365,000
3

Beds

2.1

Baths

2,294

Sq.Ft.

24607 Chestertown Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8901 S Bayview Drive Chestertown, MD MLS# MDKE2007118
  • Recently Listed with Virtual Tour
1 of 51
$525,000
3

Beds

2.1

Baths

1,833

Sq.Ft.

8901 S Bayview Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 21338 Virginia Avenue Chestertown, MD MLS# MDKE2007194
  • Recently Listed with Virtual Tour
1 of 47
$400,000
2

Beds

2.0

Baths

1,000

Sq.Ft.

21338 Virginia Avenue

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 106 Harlan Loop Chestertown, MD MLS# MDKE2007190
  • Recently Listed with Virtual Tour
1 of 68
$425,000
4

Beds

2.1

Baths

3,165

Sq.Ft.

106 Harlan Loop

Chestertown, MD

Bright
Courtesy of DOUGLAS REALTY LLC
View 203 Manor Avenue Chestertown, MD MLS# MDKE2007180
$296,000
3

Beds

1.1

Baths

1,248

Sq.Ft.

203 Manor Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 10484 Cogar Road Chestertown, MD MLS# MDKE2007056
$238,000
3

Beds

1.0

Baths

1,008

Sq.Ft.

10484 Cogar Road

Chestertown, MD

Bright
Courtesy of LPT REALTY, LLC
View 204 S Water Street Chestertown, MD MLS# MDKE2007184
$565,000
2

Beds

2.0

Baths

1,306

Sq.Ft.

204 S Water Street

Chestertown, MD

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Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 8986 Orchard Drive Chestertown, MD MLS# MDKE2007150
  • Recently Listed with Virtual Tour
1 of 54
$679,900
3

Beds

3.1

Baths

3,228

Sq.Ft.

8986 Orchard Drive

Chestertown, MD

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Courtesy of BENSON & MANGOLD, LLC
View 234 N Kent Street Chestertown, MD MLS# MDKE2007128
  • Virtual Tour
1 of 41
$325,000
5

Beds

2.0

Baths

1,802

Sq.Ft.

234 N Kent Street

Chestertown, MD

Bright
Courtesy of TTR SOTHEBY'S INTERNATIONAL REALTY
View Little Harbor Way # 1 Chestertown, MD MLS# MDKE2007154
  • New Construction
1 of 29
$1,800,000
4

Beds

3.1

Baths

3,540

Sq.Ft.

Little Harbor Way # 1

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 103 Metcalf Road Chestertown, MD MLS# MDKE2007148
  • New Construction
1 of 16
$259,900
3

Beds

2.1

Baths

1,280

Sq.Ft.

103 Metcalf Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - CHESTER
View 896 Washington Avenue Chestertown, MD MLS# MDKE2007140
$325,000
1,000

Sq.Ft.

896 Washington Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 105 N Water Street # 3 Chestertown, MD MLS# MDKE2007112
$459,000
2

Beds

2.0

Baths

1,098

Sq.Ft.

105 N Water Street # 3

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 10 Cedar Chase Court Chestertown, MD MLS# MDKE2007124
$495,000
3

Beds

2.1

Baths

1,656

Sq.Ft.

10 Cedar Chase Court

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 6324 Quaker Neck Road Chestertown, MD MLS# MDKE2007098
$2,895,000
5

Beds

3.1

Baths

5,938

Sq.Ft.

6324 Quaker Neck Road

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 22974 Bay Shore Road Chestertown, MD MLS# MDKE2007106
$315,000
2

Beds

2.0

Baths

1,440

Sq.Ft.

22974 Bay Shore Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 7712 Waterview Lane Chestertown, MD MLS# MDKE2007104
$659,999
3

Beds

2.2

Baths

2,716

Sq.Ft.

7712 Waterview Lane

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 104 Maple Avenue Chestertown, MD MLS# MDKE2007096
$1,050,000
7,296

Sq.Ft.

104 Maple Avenue

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC - ANNAPOLIS
View 8732 Elm Road Chestertown, MD MLS# MDKE2007082
$289,000
3

Beds

2.0

Baths

1,056

Sq.Ft.

8732 Elm Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY

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

$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 4
$200K - 300K 21
$300K - 400K 22
$400K - 500K 7
$500K - 600K 4
$600K - 700K 6
$700K - 800K 10
$800K - 900K 7
$900K - 1M 0
$1M - Max 16

Homes for Sale by Type in Chestertown, MD

Property Type Count
Single Family 53
Townhouse 7
Condo 15
Commercial 12
Rental 9
Lots and Land 41
Condo/Town/CoOp 0
CoOp 0
Multi Family 0
Mobile Home 0
Farms 1

(Data as of 10/25/2026)

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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