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Sell Buy Markets Guides Media Company
Housecats Co.
2077 Somerville Rd
Suite 200
Annapolis, MD 21401
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
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The Housecats Company is an Annapolis-based Compass real estate team specializing in luxury, waterfront, and lifestyle properties across Maryland and Washington, D.C. Our group brings together local expertise, market interpretation, media strategy, and client guidance across Maryland’s most distinctive communities. Sign-up to receive our newsletters and join the pride.
2077 Somerville Rd
suite 200
Annapolis, MD 21401
