View 8833 Georgetown Road Chestertown, MD MLS# MDKE2005766
$364,000
4

Beds

2.0

Baths

1,625

Sq.Ft.

8833 Georgetown Road

Chestertown, MD

Bright
Courtesy of COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANY
View 108 Flying Cloud Drive Chestertown, MD MLS# MDKE2005928
$364,900
4

Beds

2.1

Baths

1,936

Sq.Ft.

108 Flying Cloud Drive

Chestertown, MD

Bright
Courtesy of CROSS STREET REALTORS 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
The time to sell is now! THE TIME TO SELL IS NOW!
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 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 22481 Goose Hollow Drive Chestertown, MD MLS# MDKE2006012
  • Recently Listed
1 of 18
OPEN HOUSE: Sunday 1/11 1:00 PM - 3:00 PM
$379,500
3

Beds

2.0

Baths

1,296

Sq.Ft.

22481 Goose Hollow Drive

Chestertown, MD

Bright
Courtesy of REALTY MARK CITYSCAPE
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 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 6746 Quaker Neck Road Chestertown, MD MLS# MDKE2006014
$445,000
5

Beds

2.1

Baths

3,371

Sq.Ft.

6746 Quaker Neck Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 6746 Quaker Road Chestertown, MD MLS# MDKE2006022
  • Recently Listed
1 of 49
$445,000
3,371

Sq.Ft.

6746 Quaker Road

Chestertown, MD

Bright
Courtesy of DOUG ASHLEY REALTORS, LLC
View 222 Mount Vernon Avenue Chestertown, MD MLS# MDKE2005876
    1 of 30
    OPEN HOUSE: Sunday 1/11 1:00 PM - 3:00 PM
    $465,000
    4

    Beds

    2.0

    Baths

    1,656

    Sq.Ft.

    222 Mount Vernon Avenue

    Chestertown, MD

    Bright
    Courtesy of LONG & FOSTER REAL ESTATE, INC.
    View 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 201 Greenwood Avenue Chestertown, MD MLS# MDKE2006030
    • Virtual Tour
    1 of 62
    OPEN HOUSE: Sunday 1/11 12:00 PM - 2:30 PM
    $495,000
    4

    Beds

    3.0

    Baths

    3,984

    Sq.Ft.

    201 Greenwood Avenue

    Chestertown, MD

    Bright
    Courtesy of DOUG ASHLEY REALTORS, LLC
    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 100 Adela Way Chestertown, MD MLS# MDKE2005636
    • Virtual Tour
    1 of 71
    OPEN HOUSE: Sunday 1/11 12:00 PM - 2:00 PM
    $500,000
    4

    Beds

    3.1

    Baths

    3,799

    Sq.Ft.

    100 Adela Way

    Chestertown, MD

    Bright
    Courtesy of BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY
    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 218 Camelot Drive Chestertown, MD MLS# MDKE2005982
    • Virtual Tour
    1 of 57
    OPEN HOUSE: Sunday 1/11 12:00 PM - 2:00 PM
    $525,000
    5

    Beds

    3.1

    Baths

    3,932

    Sq.Ft.

    218 Camelot Drive

    Chestertown, MD

    Bright
    Courtesy of COLDWELL BANKER REALTY
    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 251 Devon Drive Chestertown, MD MLS# MDKE2005536
    $595,000
    3

    Beds

    2.1

    Baths

    3,935

    Sq.Ft.

    251 Devon Drive

    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

    109

    Estimated median home price

    $333,900
    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 - 100K34
    $100K - 200K8
    $200K - 300K10
    $300K - 400K16
    $400K - 500K8
    $500K - 600K5
    $600K - 700K5
    $700K - 800K6
    $800K - 900K5
    $900K - 1M0
    $1M - Max12

    Homes for Sale by Type in Chestertown, MD

    Property TypeCount
    Single Family40
    Townhouse8
    Condo12
    Commercial5
    Rental6
    Lots and Land42
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home0
    Farms1

    (Data as of 1/9/2026)

    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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