Chestertown 66 Good
Chestertown Livability #238 ranked city in Maryland#11,931 ranked city in the USARanks better than 59% of areas
Is This the Right Place for You? Local Insights Report
  • Uncover the key details before you move
  • Use local data to guide a smarter investment
  • Compare neighborhoods side by side
Local Insights Report

Pros and Cons of Living in Chestertown

PROS
  • Health & Safety Health & Safety

    A high score in the health and safety category is a result of good air quality and the accessibility to health facilities such as hospitals, clinics, doctors, pharmacies and fire stations.

CONS
  • Amenities Amenities

    A majority of amenities are not ideally situated within a reasonable walking distance, which may lead residents to rely on a vehicle or public transportation.

  • Commute Commute

    Public transportation is not readily available in this area and the average commute time to work could also be longer than the national average.

What's it like Living in Chestertown?

Located in the state of Maryland, Chestertown is a small-sized city with a population of 5,197 inhabitants. The majority of Chestertown residents report their race to be White; this is followed by Black and Asian. Chestertown is not known to have a high population (over 15 years old) of married people. At only 36% married, this city falls well below the national average. Not a fan of sitting in traffic during your commute to work? Chestertown offers shorter work commutes, with an average one-way commute time taking only 19 minutes, far lower than the national average of 26 minutes.

If you’re considering relocating to any new city, it could be a very discouraging task. However, it could also be a good experience if you are willing to get to know the area before actually living in Chestertown, Maryland. When searching for a new neighborhood, several key items should be considered. Safety is of utmost importance, ensuring a secure environment with low crime. Proximity to your workplace or school helps reduce commuting time and offers convenience. Access to amenities such as parks, grocery stores, and healthcare facilities enhances your daily life. Public transportation options contribute to easy mobility. A sense of community fosters a supportive and engaging environment. Lastly, the overall atmosphere should align with your desired lifestyle, ensuring a fulfilling living experience. Considering these items will guide you towards finding the perfect neighborhood that fits all your needs. To help you find the best places to live in and around Chestertown, AreaVibes has created a livability score using key metrics like amenities, crime, cost of living, education, employment and more.

With a livability score of 65/100, Chestertown is ranked #12,125 in the United States and #247 in Maryland. There are some categories that Chestertown scores poorly for, including: amenities (F). It might be worth taking a closer look to determine why.

The unemployment rate in Chestertown has consistently declined over the years and currently stands well below the national average at 0.9%. This downward trend holds the potential to reduce poverty and inequality within the region, promote higher wage levels and stimulate greater economic growth. Such positive indicators signal the overall robust health of the local economy, offering a promising outlook for its residents and fostering an environment of financial well-being and prosperity.

There are many factors that go into deciding if an area is the right fit for your lifestyle. Certain “must haves” like low crime, great schools and nearby amenities are all at the top of most people's lists. But before even considering if those options are attainable, we'll need to know if the real estate in Chestertown is actually affordable. The median home price for Chestertown homes is $467,344, which is 9.7% lower than the Maryland average. If we take a closer look at the affordability of homes in Chestertown, we’ll see that the home price to income ratio is 7.8, which is 69.6% higher than the Maryland average.

Best Places to Live in and Around Chestertown

See all the best places to live around Chestertown

How Do You Rate The Livability In Chestertown?

1. Select a livability score between 1-100
0
Awful
25
Poor
50
Average
75
Good
100
Great
2. Select any tags that apply to this area
View results

Compare Chestertown, MD Livability

City Image
    City Default Image
      vs

      Chestertown transportation information

      Statistic Chestertown Maryland National
      Average one way commute19min32min26min
      Workers who drive to work52.6%73.7%76.4%
      Workers who carpool11.3%9.3%9.3%
      Workers who take public transit1.3%8.9%5.1%
      Workers who bicycle0.9%0.3%0.6%
      Workers who walk16.6%2.4%2.8%
      Working from home14.4%4.4%4.6%
      Source: The Chestertown, MD data and statistics displayed above are derived from the United States Census Bureau American Community Survey (ACS) and include 2026 modeled data developed using proprietary methodologies.