View 103 Landing Lane Chestertown, MD MLS# MDKE2005670
$539,999
2

Beds

2.1

Baths

2,100

Sq.Ft.

103 Landing Lane

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 116 Harlan Loop Chestertown, MD MLS# MDKE2005610
$519,000
5

Beds

3.1

Baths

4,067

Sq.Ft.

116 Harlan Loop

Chestertown, MD

Bright
Courtesy of SAMSON PROPERTIES
View 100 Adela Way Chestertown, MD MLS# MDKE2005636
  • Virtual Tour
1 of 71
$515,000
4

Beds

3.1

Baths

3,799

Sq.Ft.

100 Adela Way

Chestertown, MD

Bright
Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 101 Birch Run Road Chestertown, MD MLS# MDKE2005810
$499,999
3

Beds

2.0

Baths

1,961

Sq.Ft.

101 Birch Run Road

Chestertown, MD

Bright
Courtesy of REMAX VISION
View 8620 Park Drive Chestertown, MD MLS# MDKE2005850
$499,900
4

Beds

2.1

Baths

2,524

Sq.Ft.

8620 Park Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 110 Trafford Drive Chestertown, MD MLS# MDKE2005964
$475,000
4

Beds

2.1

Baths

2,880

Sq.Ft.

110 Trafford Drive

Chestertown, MD

Bright
Courtesy of RE/MAX ADVANTAGE REALTY
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
$470,000
4

Beds

2.0

Baths

1,656

Sq.Ft.

222 Mount Vernon Avenue

Chestertown, MD

Bright
Courtesy of LONG & FOSTER REAL ESTATE, INC.
View 109 S College Avenue Chestertown, MD MLS# MDKE2005818
$449,900
3

Beds

2.1

Baths

1,216

Sq.Ft.

109 S College Avenue

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 24543 Chestertown Road Chestertown, MD MLS# MDKE2004580
$425,000
3

Beds

2.0

Baths

3,280

Sq.Ft.

24543 Chestertown Road

Chestertown, MD

Bright
Courtesy of RE/MAX EXECUTIVE
View 411 Greenwood Avenue Chestertown, MD MLS# MDKE2005824
$419,000
3

Beds

2.1

Baths

1,676

Sq.Ft.

411 Greenwood Avenue

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 304 Hadaway Drive Chestertown, MD MLS# MDKE2005848
$399,000
4

Beds

2.0

Baths

1,325

Sq.Ft.

304 Hadaway Drive

Chestertown, MD

Bright
Courtesy of CUMMINGS & CO. REALTORS
View 349 & 351 High Street Chestertown, MD MLS# MDKE2003720
$395,000
6

Beds

0.0

Baths

349 & 351 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 349 High Street Chestertown, MD MLS# MDKE2004076
$395,000
7

Beds

3.1

Baths

3,664

Sq.Ft.

349 High Street

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 517 High Street Chestertown, MD MLS# MDKE2005736
$389,900
3

Beds

0.0

Baths

517 High Street

Chestertown, MD

Bright
Courtesy of L. C. PARKER REAL ESTATE
View 860 & 870 High Street Chestertown, MD MLS# MDKE2003850
$375,000
16,977

Sq.Ft.

860 & 870 High Street

Chestertown, MD

Bright
Courtesy of TAYLOR PROPERTIES
View 7653 Broad Neck Road Chestertown, MD MLS# MDKE2005742
$375,000
4

Beds

3.0

Baths

1,790

Sq.Ft.

7653 Broad Neck Road

Chestertown, MD

Bright
Courtesy of BENSON & MANGOLD, LLC
View 108 Flying Cloud Drive Chestertown, MD MLS# MDKE2005928
$375,000
4

Beds

2.1

Baths

1,936

Sq.Ft.

108 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS LLC
View 204 Rolling Road Chestertown, MD MLS# MDKE2005896
    1 of 40
    OPEN HOUSE: Saturday 12/13 11:00 AM - 1:00 PM
    $370,000
    3

    Beds

    2.0

    Baths

    2,296

    Sq.Ft.

    204 Rolling Road

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 21111 Texas Avenue Chestertown, MD MLS# MDKE2005932
    $370,000
    3

    Beds

    2.0

    Baths

    1,680

    Sq.Ft.

    21111 Texas Avenue

    Chestertown, MD

    Bright
    Courtesy of KELLER WILLIAMS SELECT REALTORS OF EASTON
    View 112 Silver Heel Drive Chestertown, MD MLS# MDKE2005880
    $369,900
    5

    Beds

    3.1

    Baths

    2,615

    Sq.Ft.

    112 Silver Heel Drive

    Chestertown, MD

    Bright
    Courtesy of EXP REALTY, 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

    120

    Estimated median home price

    $320,000
    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 - 100K37
    $100K - 200K10
    $200K - 300K11
    $300K - 400K14
    $400K - 500K11
    $500K - 600K5
    $600K - 700K8
    $700K - 800K4
    $800K - 900K6
    $900K - 1M0
    $1M - Max14

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family49
    Townhouse9
    Condo9
    Commercial6
    Rental4
    Lots and Land44
    Condo/Town/CoOp0
    CoOp0
    Multi Family2
    Mobile Home0
    Farms1

    (Data as of 11/11/2025)

    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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