Explore Chester
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Why Live in Chester
Chester, MD, located on Kent Island between the Chester River and Chesapeake Bay, offers a blend of coastal charm and modern convenience. The area is known for its maritime atmosphere, with numerous marinas and waterfront views. Chester is 17 miles from Annapolis, home to the United States Naval Academy. Outdoor enthusiasts can enjoy Terrapin Nature Park's walking paths and tidal marshes, or the Cross Island Trail for hiking and cycling. Castle Marina provides opportunities for boating and fishing. Indoor fitness options include Club One Fitness and Aerobics. Housing in Chester ranges from ranch-style homes and colonials to New Traditional builds, with properties south of Highway 50 dating back to the mid-20th century and newer developments in the north. The area features a mix of single-family homes, condos, and townhouses, with some waterfront estates requiring additional flood insurance. Annual events like the Kent Island Crab Feast and the Annapolis Baygrass Music Festival foster community spirit. Shopping and dining are centered around Highway 50, with big-box stores like Safeway and Target, and bayside dining options in nearby Kent Narrows, including The Jetty and Bridges. Chester's schools are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving commendable scores. Highway 50 is the main transportation route, connecting Chester to Annapolis, Baltimore, and Washington, D.C., while BWI International Airport is about 30 miles away.
Home Prices in Chester, MD
The median home sale price in Chester, MD is $652,450, up 14% year-over-year. Homes in Chester sell in 292 days on average, compared to the national average of 58 days.
Home Price Trends
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Median Sale Price
$652,450
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Median Single Family Sale Price
$700,000
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Median Townhouse Sale Price
$374,900
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Median 2 Bedroom Sale Price
$599,900
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Median 1 Bedroom Sale Price
$269,000
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Average Price Per Sq Ft
$300
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Number of Homes for Sale
75
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Last 12 months Home Sales
228
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Months of Supply
3.90
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Median List Price
$679,450
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Median Change From 1st List Price
0%
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Median Home Sale Price YoY Change
14%
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