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Eastern Shore
Chestertown
Annual 2025 | Overall Market
LIFESTYLE
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.
the draw
Chestertown blends historic charm with a relaxed pace of life, attracting residents drawn to community, heritage, and a quieter Eastern Shore setting.
The Big Picture
175
TOTAL TRANSACTIONS
$379,989
average sales price
19
average days on market
single family homes
TOTAL TRANSACTIONS
149
median sales price
$390,000
median days on market
19
townhouses
TOTAL TRANSACTIONS
21
median sales price
$280,000
median days on market
23
condominiums
TOTAL TRANSACTIONS
0
median sales price
--
median days on market
0
total sales volume
$84,653,901
highest sales price
$4,221,800
featured communities
More Than Real Estate.
It’s How You Live Here.
Buying or selling a home is just the start.
What matters is understanding the place around it — the market, the lifestyle, the culture, the communities, and the forces shaping what comes next.
That’s what we do.
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2077 Somerville Rd
Annapolis, MD 21401