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Homes for Sale

Chestertown Open Houses

103 Metcalf Rd
Chestertown, MD 21620

$259,900, 3 Beds, 2 Baths

103 Landing Ln
Chestertown, MD 21620

$499,999, 2 Beds, 3 Baths

101 S Mill St
Chestertown, MD 21620

$515,000, 2 Beds, 3 Baths

22481 Goose Hollow Dr
Chestertown, MD 21620

$279,900, 3 Beds, 2 Baths

102 Flying Cloud Dr
Chestertown, MD 21620

$329,900, 3 Beds, 3 Baths

Chestertown Home Report

Average Home

Average Price

$603,772

Avg Bedrooms

3.3 beds

Avg Bathrooms

2.69 baths

Average Price By Bedrooms

1 bedroom

$275,000

2 bedrooms

$341,488

3 bedrooms

$532,124

4 bedrooms

$729,682

5 bedrooms

$877,071

See additional market statistics

Last updated July 13, 2026.

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18+ Waterfront Homes for Sale in Chestertown

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eXp Realty | Montague Properties

Melanie Montague

5010 Connecticut Ave #500
Washington, DC 20036

License #573553

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Melanie Montague - eXp Realty - Montague Properties - Winback participates, and is provided by BRIGHT through a licensing agreement. 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 Closed or are no longer being offered for sale. © 2026 BRIGHT, All Rights Reserved Information Deemed Reliable But Not Guaranteed. Data last updated: July 13, 2026 4 PM.