Chestertown
Chestertown combines historic architecture, a walkable downtown, and a strong connection to the Chester River. Known for its academic and cultural influences, the town attracts residents drawn to heritage, community, and a slower pace of life. Market activity here is shaped by fit and character, with long-term ownership playing a central role.
Lifestyle
The Draw
Chestertown blends historic charm with a relaxed pace of life, attracting residents drawn to community, heritage, and a quieter Eastern Shore setting.
175Total Transactions | $379,989Average Sales Price | 19Average Days on Market |
Single-Family Homes | Townhouses | Condominiums |
Total Transactions 149 | Total Transactions 21 | Total Transactions 0 |
Median Sales Price $390,000 | Median Sales Price $280,000 | Median Sales Price -- |
Median Days on Market 19 | Median Days on Market 23 | Median Days on Market 0 |
Total Sales Volume $84,653,901 | Highest Sales Price $4,221,800 |
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