Current Search

x Chestertown

x 1+ beds

x Has Waterfront Lot

Clear All

Homes for Sale

Chestertown Home Report

Average Home

Average Price

$508,009

Avg Bedrooms

2.37 beds

Avg Bathrooms

1.86 baths

Average Price By Bedrooms

1 bedroom

$200,000

2 bedrooms

$281,499

3 bedrooms

$500,764

4 bedrooms

$637,823

5 bedrooms

$927,175

See additional market statistics

Last updated April 11, 2026.

Quick Searches

Homes for Sale in 20601

Homes for Sale in 20602

Homes for Sale in 20603

Homes for Sale in 20613

Homes for Sale in 20639

Homes for Sale in 20646

Homes for Sale in 20653

Homes for Sale in 20657

Homes for Sale in 20678

Homes for Sale in 20695

Homes for Sale in 21037

Homes for Sale in 21403

Homes for Sale in 21409

Homes for Sale in Annapolis

Homes for Sale in Anne Arundel County

Homes for Sale in Baltimore

Homes For Sale In Bowie

Homes for Sale in Brandywine

Homes for Sale in Broadneck

Homes for Sale in Calvert County

Homes for Sale in Cape St Claire

Homes For Sale In Centreville

Homes for Sale in Charles County

Homes For Sale In Chesapeake Beach

Homes for Sale in Chestertown

Homes For Sale In Crofton

Homes for Sale in Dunkirk

Homes for Sale in Eastern Shore

Homes for Sale in Easton

Homes for Sale in Eastport

Homes for Sale in Hollywood

Homes for Sale in Hughesville

Homes for Sale in Huntingtown

Homes for Sale in La Plata

Homes for Sale in Leonardtown

Homes for Sale in Lexington Park

Homes For Sale In Lusby

Homes for Sale in Mechanicsville

Homes For Sale In North Beach

Homes for Sale in North Point

Homes for Sale in Patuxent

Homes for Sale in Prince Georges County

Homes for Sale in Queen Annes County

Homes for Sale in Saint Marys County

Homes for Sale in Severna Park

Homes for Sale in St. Charles

Homes for Sale in St. Marys County

Homes for Sale in Thomas Stone

Homes for Sale in Towson

Homes for Sale in Upper Marlboro

Homes for Sale in Waldorf

Homes for Sale in White Plains

Waterfront Homes for Sale in Annapolis

Waterfront Homes for Sale in Edgewater

Waterfront Homes for Sale in Lusby

28+ Waterfront Homes for Sale in Chestertown

Sort:

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: April 11, 2026 9 PM.