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 103 Trafford Drive Chestertown, MD MLS# MDKE2006416
$419,900
3

Beds

2.1

Baths

1,944

Sq.Ft.

103 Trafford Drive

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 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
The time to sell is now! THE TIME TO SELL IS NOW!
View 24295 Langford Road Chestertown, MD MLS# MDKE2006320
    1 of 71
    OPEN HOUSE: Saturday 6/6 2:30 PM - 4:30 PM
    $445,000
    2

    Beds

    2.1

    Baths

    1,857

    Sq.Ft.

    24295 Langford Road

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View 115 Acorn Drive Chestertown, MD MLS# MDKE2006360
    $296,000
    2

    Beds

    2.1

    Baths

    1,864

    Sq.Ft.

    115 Acorn Drive

    Chestertown, MD

    Bright
    Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
    View 21217 Texas Avenue Chestertown, MD MLS# MDKE2006364
    $244,500
    2

    Beds

    1.0

    Baths

    912

    Sq.Ft.

    21217 Texas Avenue

    Chestertown, MD

    Bright
    Courtesy of RE/MAX LEADING EDGE
    View 108 Pine Street Chestertown, MD MLS# MDKE2006322
    $115,000
    3

    Beds

    1.0

    Baths

    910

    Sq.Ft.

    108 Pine Street

    Chestertown, MD

    Bright
    Courtesy of REAL BROKER, LLC - CHESTER
    View 10584 Klamath Road Chestertown, MD MLS# MDKE2006328
    • New Construction
    1 of 20
    $319,900
    3

    Beds

    1.1

    Baths

    10584 Klamath Road

    Chestertown, MD

    Bright
    Courtesy of REAL BROKER, LLC - CHESTER
    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
    $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
    $340,000
    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
    $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
    $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 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 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

    122

    Estimated median home price

    $345,000
    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

    PriceCount
    $0 - 100K30
    $100K - 200K8
    $200K - 300K15
    $300K - 400K18
    $400K - 500K12
    $500K - 600K5
    $600K - 700K4
    $700K - 800K8
    $800K - 900K6
    $900K - 1M0
    $1M - Max16

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family52
    Townhouse5
    Condo17
    Commercial9
    Rental12
    Lots and Land39
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home0
    Farms0

    (Data as of 6/4/2026)

    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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