View 108 Pine Street Chestertown, MD MLS# MDKE2006322
$142,641
1

Beds

1.0

Baths

910

Sq.Ft.

108 Pine Street

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 10584 Klamath Road Chestertown, MD MLS# MDKE2006328
$319,900
2

Beds

2.0

Baths

10584 Klamath Road

Chestertown, MD

Bright
Courtesy of REAL BROKER, LLC
View 201 Birch Run Road Chestertown, MD MLS# MDKE2006316
$435,000
3

Beds

2.0

Baths

1,588

Sq.Ft.

201 Birch Run Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
The time to sell is now! THE TIME TO SELL IS NOW!
View Cogar Road Chestertown, MD MLS# MDKE2006304
  • Recently Listed
1 of 3
$3,000
Studio

Beds

0.0

Baths

Cogar Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View 103 Flying Cloud Drive Chestertown, MD MLS# MDKE2006154
$339,900
3

Beds

2.1

Baths

1,724

Sq.Ft.

103 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of AMERICAN PREMIER REALTY, LLC
View 139 Prospect Street Chestertown, MD MLS# MDKE2006250
  • Recently Listed
1 of 28
OPEN HOUSE: Saturday 4/4 11:00 AM - 1:00 PM
$225,000
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
$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
$225,000

Haacke Drive Lot 3

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
View 202 Waldo Drive Chestertown, MD MLS# MDKE2006260
  • Recently Listed
1 of 3
$389,000
3

Beds

1.1

Baths

2,055

Sq.Ft.

202 Waldo Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View Lenapah Rd Chestertown, MD MLS# MDKE2006284
  • Recently Listed
1 of 3
$3,000
Studio

Beds

0.0

Baths

Lenapah Rd

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP LLC
View Tonopah Road Chestertown, MD MLS# MDKE2006286
  • Recently Listed
1 of 3
$3,000
Studio

Beds

0.0

Baths

Tonopah Road

Chestertown, MD

Bright
Courtesy of ASHLAND AUCTION GROUP 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 106 Queen Street S Chestertown, MD MLS# MDKE2006152
    1 of 70
    OPEN HOUSE: Friday 4/3 5:00 PM - 7:00 PM
    $865,000
    3

    Beds

    3.1

    Baths

    2,472

    Sq.Ft.

    106 Queen Street S

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View 107 Conley Drive Chestertown, MD MLS# MDKE2006220
    $170,000
    3

    Beds

    1.0

    Baths

    1,140

    Sq.Ft.

    107 Conley Drive

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    View 8276 Broad Neck Road Chestertown, MD MLS# MDKE2006216
    $1,495,000
    4

    Beds

    3.1

    Baths

    3,383

    Sq.Ft.

    8276 Broad Neck Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 104 Flying Cloud Drive Chestertown, MD MLS# MDKE2006212
    $399,900
    5

    Beds

    3.1

    Baths

    2,535

    Sq.Ft.

    104 Flying Cloud Drive

    Chestertown, MD

    Bright
    Courtesy of REAL BROKER, LLC
    View 515 N Kent Street Chestertown, MD MLS# MDKE2006204
    $495,000
    4

    Beds

    2.1

    Baths

    2,220

    Sq.Ft.

    515 N Kent Street

    Chestertown, MD

    Bright
    Courtesy of CROSS STREET REALTORS LLC
    View 21125 Iowa Avenue Chestertown, MD MLS# MDKE2006198
    $339,900
    2

    Beds

    1.0

    Baths

    1,294

    Sq.Ft.

    21125 Iowa Avenue

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, 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

    106

    Estimated median home price

    $339,900
    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 - 100K29
    $100K - 200K7
    $200K - 300K11
    $300K - 400K14
    $400K - 500K11
    $500K - 600K5
    $600K - 700K5
    $700K - 800K7
    $800K - 900K6
    $900K - 1M0
    $1M - Max11

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family37
    Townhouse7
    Condo17
    Commercial7
    Rental9
    Lots and Land37
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms0

    (Data as of 3/31/2026)

    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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