View Cromwell Clark Road Chestertown, MD MLS# MDKE2005156
$3,000,000
Studio

Beds

0.0

Baths

Cromwell Clark Road

Chestertown, MD

Bright
Courtesy of THE LAND GROUP
View 7989 Quaker Neck Road Chestertown, MD MLS# MDKE2005590
$2,500,000
5

Beds

4.1

Baths

4,305

Sq.Ft.

7989 Quaker Neck Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 10121 Fairlee Road Chestertown, MD MLS# MDKE2005852
$2,350,000
6

Beds

5.0

Baths

4,954

Sq.Ft.

10121 Fairlee 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 10121 Fairlee Road Chestertown, MD MLS# MDKE2005866
$2,350,000
6

Beds

5.0

Baths

4,954

Sq.Ft.

10121 Fairlee Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View Little Harbor Way # 1 Chestertown, MD MLS# MDKE2004992
  • New Construction with Virtual Tour
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 Little Harbor Way # 1 Chestertown, MD MLS# MDKE2005768
  • New Construction with Virtual Tour
1 of 25
$1,459,000
3

Beds

2.1

Baths

2,231

Sq.Ft.

Little Harbor Way # 1

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 105 High Street Chestertown, MD MLS# MDKE2005890
    1 of 59
    OPEN HOUSE: Saturday 12/6 12:00 PM - 2:00 PM
    $1,395,500
    5

    Beds

    4.1

    Baths

    3,243

    Sq.Ft.

    105 High Street

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
    View 120 Speer Road Chestertown, MD MLS# MDKE2005054
    $1,250,000
    9,604

    Sq.Ft.

    120 Speer Road

    Chestertown, MD

    Bright
    Courtesy of MACKENZIE COMMERCIAL R E SVCS, LLC
    View 329 High Street Chestertown, MD MLS# MDKE2005172
    $1,250,000
    3,900

    Sq.Ft.

    329 High Street

    Chestertown, MD

    Bright
    Courtesy of CROSS STREET REALTORS LLC
    View 23393 Cacaway Farm Lane Chestertown, MD MLS# MDKE2004002
    $1,195,000
    3

    Beds

    3.1

    Baths

    4,446

    Sq.Ft.

    23393 Cacaway Farm Lane

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 206 Cannon Street Chestertown, MD MLS# MDKE2003606
    $1,150,000
    1

    Sq.Ft.

    206 Cannon Street

    Chestertown, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View 206 Cannon Street Chestertown, MD MLS# MDKE2003620
    $1,150,000
    Studio

    Beds

    0.0

    Baths

    206 Cannon Street

    Chestertown, MD

    Bright
    Courtesy of BENSON & MANGOLD, LLC
    View #25 Landing Lane Chestertown, MD MLS# MDKE2005954
    • Recently Listed
    1 of 22
    $1,099,900
    4

    Beds

    3.1

    Baths

    2,784

    Sq.Ft.

    #25 Landing Lane

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 515 Washington Avenue Chestertown, MD MLS# MDKE2000776
    $899,000
    42,000

    Sq.Ft.

    515 Washington Avenue

    Chestertown, MD

    Bright
    Courtesy of ESHORE
    View 228 S Water St Chestertown, MD MLS# MDKE2005812
    • New Construction
    1 of 32
    $878,000
    3

    Beds

    3.1

    Baths

    2,310

    Sq.Ft.

    228 S Water St

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 201 N Lynchburg Street Chestertown, MD MLS# MDKE2005278
    $850,000
    2,045

    Sq.Ft.

    201 N Lynchburg Street

    Chestertown, MD

    Bright
    Courtesy of RE/MAX ASSOCIATES-HOCKESSIN
    View 104 Little Harbor Way Chestertown, MD MLS# MDKE2005894
    $849,900
    3

    Beds

    2.1

    Baths

    1,980

    Sq.Ft.

    104 Little Harbor Way

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 102 Little Harbor Way Chestertown, MD MLS# MDKE2005950
    $839,500
    3

    Beds

    2.1

    Baths

    1,964

    Sq.Ft.

    102 Little Harbor Way

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 104 Landing Lane Chestertown, MD MLS# MDKE2005952
    • Recently Listed
    1 of 24
    $813,900
    3

    Beds

    3.1

    Baths

    2,192

    Sq.Ft.

    104 Landing Lane

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE
    View 106 Landing Lane Chestertown, MD MLS# MDKE2005892
    • New Construction
    1 of 24
    $799,900
    3

    Beds

    3.1

    Baths

    2,092

    Sq.Ft.

    106 Landing Lane

    Chestertown, MD

    Bright
    Courtesy of GUNTHER-MCCLARY REAL ESTATE

    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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