Homes for sale in Chestertown, MD
Figures for Chestertown, MD, week ending October 25, 2026. Last week's read — this week's is still being written.
Paige
watching Chestertown · 134 homes for sale
Paige
The most notable move in Chestertown this week was at 105 High Street, where the asking price was brought down from $1,395,500 to $1,195,000. If you want to look at a couple of options, 24607 Chestertown Road is a 3 bedrooms residential listed 11 days ago for $365,000. You could also see 7655 James Lane, a 3 bedrooms residential 15 days on market at $519,900. Looking at the wider picture, only 1 new home came on the market while 5 sellers took price cuts, showing that activity is leaning heavily on existing options. With 134 total homes for sale sitting a median of 69 days on market, inventory is lingering longer than the recent sales that closed in a median of 64 days.
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