View 104 Conley Drive Chestertown, MD MLS# MDKE2003806
$234,900
3

Beds

1.1

Baths

1,280

Sq.Ft.

104 Conley Drive

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
View 117 Water Street N # 2B Chestertown, MD MLS# MDKE2003732
$405,000
1

Beds

1.0

Baths

850

Sq.Ft.

117 Water Street N # 2B

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 207 Pondview Court Chestertown, MD MLS# MDKE2003816
$499,000
5

Beds

3.1

Baths

2,878

Sq.Ft.

207 Pondview Court

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 349 & 351 High Street Chestertown, MD MLS# MDKE2003720
$425,000
6

Beds

0.0

Baths

349 & 351 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 0 Gateway Drive Chestertown, MD MLS# MDKE2003756
$100,000
Studio

Beds

0.0

Baths

0 Gateway Drive

Chestertown, MD

Bright
Courtesy of COTTAGE STREET REALTY LLC
View 10605 Tonopah Road Chestertown, MD MLS# MDKE2003746
$299,900
4

Beds

2.0

Baths

1,248

Sq.Ft.

10605 Tonopah Road

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 9062 Fairlee Road Chestertown, MD MLS# MDKE2003724
$325,000
3

Beds

2.0

Baths

1,344

Sq.Ft.

9062 Fairlee Road

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View Cloquet Chestertown, MD MLS# MDKE2003654
$70,000
Studio

Beds

0.0

Baths

Cloquet

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES HOMESALE REALTY
View 9816 Fairlee Road Chestertown, MD MLS# MDKE2003632
$499,000
3

Beds

3.0

Baths

1,624

Sq.Ft.

9816 Fairlee Road

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View Map 36 Parcel 80 Watertower Road Chestertown, MD MLS# MDKE2003624
$55,000
Studio

Beds

0.0

Baths

Map 36 Parcel 80 Watertower Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 8757 Orchard Drive Chestertown, MD MLS# MDKE2003556
  • Virtual Tour
1 of 37
OPEN HOUSE: Saturday 5/11 11:00 AM - 1:00 PM
$498,000
2

Beds

2.1

Baths

2,210

Sq.Ft.

8757 Orchard Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View Elm Road Chestertown, MD MLS# MDKE2003590
$20,000
Studio

Beds

0.0

Baths

Elm Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Lot 24 & 25 Buck Neck Road Chestertown, MD MLS# MDKE2003512
$8,000
Studio

Beds

0.0

Baths

Lot 24 & 25 Buck Neck Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Millbrook Drive Chestertown, MD MLS# MDKE2003562
$22,000
Studio

Beds

0.0

Baths

Millbrook Drive

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 23690 L Road Chestertown, MD MLS# MDKE2003424
$25,000
Studio

Beds

0.0

Baths

23690 L Road

Chestertown, MD

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Courtesy of KELLER WILLIAMS FLAGSHIP OF MARYLAND
View 9020 Cumberland Street Chestertown, MD MLS# MDKE2003374
$297,000
2

Beds

2.0

Baths

1,150

Sq.Ft.

9020 Cumberland Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Elm Road Chestertown, MD MLS# MDKE2003416
$40,000
Studio

Beds

0.0

Baths

Elm Road

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View Montgomery Avenue Chestertown, MD MLS# MDKE2003418
$40,000
Studio

Beds

0.0

Baths

Montgomery Avenue

Chestertown, MD

Bright
Courtesy of THE HOGANS AGENCY
View Caulks Field Road Chestertown, MD MLS# MDKE2003398
$30,000
Studio

Beds

0.0

Baths

Caulks Field Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 23683 L Road Chestertown, MD MLS# MDKE2003390
$25,000
Studio

Beds

0.0

Baths

23683 L Road

Chestertown, MD

Bright
Courtesy of THE LAND GROUP

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

92

Estimated median home price

$309,450
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

PriceCount
$0 - 100K33
$100K - 200K5
$200K - 300K8
$300K - 400K7
$400K - 500K8
$500K - 600K0
$600K - 700K3
$700K - 800K4
$800K - 900K8
$900K - 1M5
$1M - Max11

Homes for Sale by Type in Chestertown, MD

Property TypeCount
Single Family34
Townhouse7
Condo4
Commercial5
Rental13
Lots and Land37
Condo/Town/CoOp0
CoOp0
Multi Family4
Mobile Home0
Farms1

(Data as of 5/9/2024)

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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