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    Chestertown

    Chestertown town, Maryland

    About Chestertown

    Chestertown, Maryland, a charming gem on the Eastern Shore, offers a lifestyle that feels worlds away from the hustle of city life, yet is surprisingly accessible. Imagine strolling along cobblestone streets, lined with historic brick buildings, with the Chester River glistening nearby. Here, affordability meets charm. The median home value of $302,200 is significantly lower than the national average, making homeownership a realistic dream for many. With a population of just over 5,500, Chestertown fosters a strong sense of community, where neighbors know each other and local events are well-attended. It's a place where you can truly slow down, breathe the fresh air, and enjoy a quality of life that's increasingly rare.

    From an investment perspective, Chestertown presents a compelling case. While the median household income of $43,980 is below the national average, the lower cost of living provides a more favorable financial landscape. The town's low crime rates contribute to a secure environment, perfect for families and retirees. The housing market offers a variety of options, from historic homes to modern builds, all within a walkable downtown area. Chestertown is ideally suited for those seeking a tranquil, affordable lifestyle with a strong sense of community, offering a blend of small-town charm and access to the cultural and recreational opportunities of the Chesapeake Bay.

    Chestertown, Maryland at a Glance

    Chestertown is a city in Chestertown town, Maryland with a population of approximately 5,522. The median home value is $302,200 and the median household income is $43,980.. The violent crime rate is 6.6 per 1,000 residents, compared to the national average of 3.6.. Median rent is $982 per month. Data sourced from the US Census Bureau, FBI Crime Data Explorer, EPA, Walk Score, and FEMA.

    Median Home Value

    $302,200

    Median Income

    $43,980

    Population

    5,522

    Walk Score

    N/A

    Air Quality

    N/A

    Climate Risk

    N/A

    Kurby ScoreLimited Data
    72
    B+

    Good

    Affordability63/100
    Safety95/100
    Economy60/100
    Walkability & Transit: UnavailableEducation: UnavailableEnvironment: Unavailable

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    Demographics
    Population
    5,522
    Median Age
    N/A
    Median Household Income
    $43,980

    41% below nat'l avg

    Bachelor's Degree+
    N/A
    Poverty Rate
    16.2%

    31% above nat'l avg

    Housing
    Median Home Value
    $302,200

    7% above nat'l avg

    Median Rent
    $982

    16% below nat'l avg

    Homeownership Rate
    47.1%

    29% below nat'l avg

    Affordability Index
    N/A
    Safety
    Violent Crime Rate
    6.6 per 1K

    83% above nat'l avg

    Property Crime Rate
    44.7 per 1K

    135% above nat'l avg

    Livability
    Walk Score
    N/A
    Transit Score
    N/A
    Bike Score
    N/A

    Want a detailed report for a specific address in Chestertown?

    Air Quality
    AQI
    N/A
    Category
    N/A
    Climate Risk
    Overall Risk
    N/A
    Risk Score
    N/A
    Noise Levels
    Overall
    N/A
    Road Traffic
    N/A
    Aviation
    N/A
    Rail
    N/A
    Utility Costs
    Electricity Rate
    N/A
    Est. Monthly Electric
    N/A
    Employment
    Unemployment Rate
    3.9%

    5% above nat'l avg

    Poverty Rate
    16.2%

    31% above nat'l avg

    Weather & Climate in Chestertown

    Avg High

    66°F

    Avg Low

    49°F

    Annual Rainfall

    53.4"

    Avg Humidity

    69%

    Monthly Temperature (°F)
    Monthly Precipitation (inches)

    Political Landscape

    Political Leaning
    Leans Democratic
    DemocratRepublican

    → Politically stable

    Based on Anne Arundel County county-level presidential election data

    Presidential Election Results

    Culture & Things to Do in Chestertown

    Attractions & Landmarks
    📜Sultana Education Foundation(historic)
    🏗️Chestertown Marina(landmark)
    🖼️RiverArts Gallery & Gift Shop(gallery)
    📜Washington College(historic)
    🌳Wilmer Park(park)
    📜Chestertown Historic District(historic)
    📜Kent County Courthouse(historic)
    📜Custom House(historic)
    Local Events & Festivals

    Chestertown Tea Party Festival

    Annual festival commemorating the 1774 Chestertown Tea Party.

    Chestertown Arts & Entertainment District First Friday

    Monthly event featuring art, music, and local businesses.

    Kent County Fair

    Annual agricultural fair with exhibits, rides, and entertainment.

    Downrigging Weekend

    Tall ship and maritime heritage festival.

    Things to Know Before Moving

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