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Price cuts this week in Chestertown, MD

Figures for Chestertown, MD, week ending September 15, 2026.

Paige

Price cuts · Chestertown

Paige

9 sellers in Chestertown cut the asking price in the last 7 days, a median reduction of 8.7 percent. The median asking price across everything for sale in Chestertown is $315,000, and what is listed has been on the market a median of 69 days. These are the homes that moved. What are you looking for in Chestertown?

1003 TWIN COURT

For SaleBright MLS

1003 TWIN COURT, Chestertown

3 bd · 3 ba · House · 28 DOM

MDKE2006974, Cross Street Realtors LLC

101 COLLEGE AVENUE

For SaleBright MLS

101 COLLEGE AVENUE, Chestertown

2 bd · 2 ba · House · 37 DOM

MDKE2006918, Doug Ashley Realtors, LLC

10540 TONOPAH ROAD

For SaleBright MLS

10540 TONOPAH ROAD, Chestertown

3 bd · 2 ba · House · 46 DOM

MDKE2006880, Doug Ashley Realtors, LLC

9126 FAIRLEE ROAD

For SaleBright MLS

9126 FAIRLEE ROAD, Chestertown

3 bd · 2 ba · House · 78 DOM

MDKE2006764, Chesapeake Real Estate Associates, LLC

6746 QUAKER NECK ROAD

For SaleBright MLS

6746 QUAKER NECK ROAD, Chestertown

5 bd · 3 ba · House · 258 DOM

MDKE2006014, Doug Ashley Realtors, LLC

Tap a home and I'll open it here — we can keep talking about it.

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