


105 High Street, Chestertown, MD 21620
Listing Courtesy of Coldwell Banker Chesapeake Real Estate Company

Sold onDecember 1, 2025· Listed at $1,250,000
This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.
From within and without, from the front, the sides and the back, this exceptional 1876 and 1998 residence sings. Every passer-by has stopped and gazed upon the wrap around porch. No doubt, many a conversation "over the railing" has taken place for decades. Those fortunate enough to have enjoyed hospitality inside this German-wood clad home have experienced both its expansive flow of inter-connected rooms with center hall, the cozy grandness of an era long ago and comfortable living today amidst an eclectic mix of modern art and furniture, antiques, and other treasures. Prominent historic downt...
Listing updated: December 2, 2025 at 12:56 AM
Listed by:
Richard Keaveney (410) 708-6470, Cross Street Realtors LLC
Source: Bright MLS · MLS #MDKE2005728
| Date | Event | Price |
|---|---|---|
| Dec 1, 2025 | Sold | $1,165,000 |
| Oct 5, 2025 | Listed for sale | $1,250,000 |
119 High Street, Chestertown, MD 21620
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This home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.
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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Samson Properties participates, and is provided by BRIGHT through a licensing agreement. © 2026 Bright MLS, All Rights Reserved. Information deemed reliable but not guaranteed. 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. Data last updated: 7/22/2026.