Homes for sale in Chestertown, MD
Figures for Chestertown, MD, week ending September 15, 2026.
Paige
watching Chestertown · 139 homes for sale
Paige
The biggest shift in town this week was at 6746 Quaker Neck Road, where the asking price on that residential property dropped from $445,000 down to $339,000. It is a clear sign that sellers are making moves right now. Two properties currently available include 1003 Twin Court, a 3 bedroom residential home listed 27 days ago that reduced to $499,900 from $524,900. There is also 101 S College Avenue, a 2 bedroom residential home listed 36 days ago, asking $359,000 after dropping from $369,000. Looking at the wider market, 19 homes sold in the last 30 days at a median sold price of $330,000 after spending a median of 23 days on market before selling. Meanwhile, the median days on market for what is currently listed sits higher at 69 days, with 9 properties taking a median reduction of 8.7% over the last 7 days as new inventory slows.
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