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 #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
The time to sell is now! THE TIME TO SELL IS NOW!
View #35 Landing Lane Chestertown, MD MLS# MDKE2005956
  • Recently Listed
1 of 26
$786,900
3

Beds

2.1

Baths

1,964

Sq.Ft.

#35 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View #36 Landing Lane Chestertown, MD MLS# MDKE2005958
  • Recently Listed
1 of 26
$753,500
3

Beds

2.1

Baths

1,964

Sq.Ft.

#36 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View #37 Landing Lane Chestertown, MD MLS# MDKE2005960
  • Recently Listed
1 of 24
$765,900
3

Beds

2.1

Baths

1,964

Sq.Ft.

#37 Landing Lane

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 311 Devon Drive Chestertown, MD MLS# MDKE2005930
  • Recently Listed with Virtual Tour
1 of 40
$598,000
5

Beds

3.1

Baths

3,504

Sq.Ft.

311 Devon Drive

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, 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 Georgetown Road Chestertown, MD MLS# MDKE2005844
  • Recently Listed
1 of 7
$89,500
Studio

Beds

0.0

Baths

Georgetown Road

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
View 7521 Pine Avenue Chestertown, MD MLS# MDKE2005920
  • Recently Listed
1 of 24
OPEN HOUSE: Saturday 12/6 12:00 PM - 1:00 PM
$265,000
3

Beds

1.0

Baths

1,040

Sq.Ft.

7521 Pine Avenue

Chestertown, MD

Bright
Courtesy of CHESAPEAKE REAL ESTATE ASSOCIATES, LLC
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 108 Little Harbor Way Chestertown, MD MLS# MDKE2005902
$635,000
Studio

Beds

0.0

Baths

108 Little Harbor Way

Chestertown, MD

Bright
Courtesy of GUNTHER-MCCLARY REAL ESTATE
View 611 Cannon Street Chestertown, MD MLS# MDKE2005906
$299,000
2

Beds

1.1

Baths

920

Sq.Ft.

611 Cannon Street

Chestertown, MD

Bright
Courtesy of SELECT LAND & HOMES, LLC
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 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 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
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 204 Rolling Road Chestertown, MD MLS# MDKE2005896
    $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 101 Metcalf Road Chestertown, MD MLS# MDKE2005882
    • New Construction
    1 of 26
    $264,900
    3

    Beds

    1.1

    Baths

    1,280

    Sq.Ft.

    101 Metcalf Road

    Chestertown, MD

    Bright
    Courtesy of REAL BROKER, LLC
    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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