Winchester 91 Exceptional
Winchester Livability #2 ranked city in Massachusetts#62 ranked city in the USARanks better than 99% of areas
Is This the Right Place for You? Local Insights Report
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Pros and Cons of Living in Winchester

PROS
  • Amenities Amenities

    Conveniently located, the area boasts a variety of amenities, including grocery stores, shopping, coffee shops and entertainment options all within walking distance.

  • Commute Commute

    The high commute score in this area could imply easy access to public transportation, as well as shorter-than-average commute times to your workplace.

  • Crime Crime

    This area boasts a crime rate that is far below the national average, making it a very safe place to live. These crime statistics encompass both property and violent offenses.

  • Employment Employment

    With higher than average median household income, income per capita and lower unemployment rates, this area scores extremely well in the employment category.

  • Housing Housing

    Impressive scores in the housing category characterize this area, potentially attributed to the availability of affordable housing, strong appreciation rates and high home values.

CONS
  • Cost Of Living Cost Of Living

    This area is known for its high cost of living, which means you should anticipate higher costs for everyday goods and services, housing, groceries, and health care.

What's it like Living in Winchester?

Winchester is a mid-sized city located in the state of Massachusetts. The city has a population of 23,430 inhabitants. In Winchester, there are 3,883 people per square mile, which is well above the national population density average. According to the most recent Census, 79% of Winchester residents are White, 15% Asian and 1% Black. An important consideration when living in Winchester is the longer-than-average commute times. If you seek a short work commute, this area may not be the best choice for you. The one-way commute time here typically takes 34 minutes, far surpassing the national average of 26 minutes.

Whether you’re relocating to a new area to be closer to family, friends or for a new job, living in Winchester could be a positive experience compared to other cities in Massachusetts if you know where to look. Don't forget to determine what matters most to you in a neighborhood. Consider factors such as safety, proximity to work or school, access to amenities (like parks, fitness facilities, grocery stores, restaurants), public transportation options, community atmosphere and the overall vibe you're looking for. Using the livability score which includes data from categories like cost of living, health & safety, employment, you can easily compare the best places to live in Winchester and also determine if there are any nearby cities that might be a better match for your lifestyle. You can also compare Winchester to Massachusetts and the national average.

Using data and statistics Winchester has received a livability score of 91/100. This score is ranked in the 99th percentile when compared to all other cities. Clearly, Winchester is doing something right, as this score ranks well above the average of most cities. The cherry on top is that Winchester also ranks in the top 10 percent of all cities. Based on the grades for each individual category, Winchester has been rewarded with high marks for amenities (A+), crime (A+), education (A+) and housing (B+). There are some categories that Winchester ranks poorly for, including: cost of living (F). It might be worth taking a closer look to find out why.

The mantra of real estate, "location, location, location," underscores the importance of where a property is situated, making it a pivotal factor in your quest for a new home. Fortunately, when you're living in Winchester, you'll discover an abundance of exceptional local amenities and lots of things to do. Among these are conveniently located grocery stores, charming coffee shops, diverse dining options and plenty of spacious parks. These local amenities contribute significantly to its overall appeal, ensuring that your daily needs are met and offering ample opportunities for leisure and recreation. When considering your next move, the thriving local scene in Winchester undoubtedly enhances its desirability, affirming the significance of its prime location.

Low violent crime rates (murder, rape, robbery, assault) provide a safer environment for residents, reducing the risk of personal harm, property theft or violence. Low crime can also lead to increased property values and desirability. With 17 crimes per 100,000 residents, Winchester has a violent crime rate that is far below the national average.

When contemplating a move, job prospects often top the list of priorities. In Winchester, the outlook for new employment is notably brighter than in many other areas. The low unemployment rate of 1.9% points to a surge in job opportunities, the potential for higher wages, enhanced workforce productivity and increased economic growth. These favorable conditions bode well for individuals seeking career advancement and financial stability, making this area an appealing destination for those prioritizing professional opportunities and economic prosperity.

Test scores serve as a vital gauge of a school's academic prowess and the proficiency of its students. They play a pivotal role in assessing whether local schools can deliver a robust educational foundation for children. In Winchester, the schools boast an impressive average test score of 81%, significantly higher than the national average. This outstanding academic achievement not only reflects the excellence of the local educational system, but also indicates the potential for students to thrive academically, making it an attractive destination for families seeking a high-quality education for their children.

A healthy real estate market serves as a key economic indicator. It could signify overall local economic strength, stability and reflects consumer confidence in the area. Based on multiple factors including: median home and rental prices, appreciation rates and home affordability, Winchester has received high marks in the housing category. Based on these calculations, the apartment rental and real estate market appears to be very healthy.

Winchester real estate prices and overall affordability will play a huge role in determining if the area is the right fit for you. Of course there are probably some other items on your “wish list”, but even before they are considered, let’s take a look at the home prices and affordability in Winchester. Median real estate prices in Winchester come in at $1,758,709, which is 181.7% higher than the Massachusetts average. The home price to income ratio compares the median home prices to the median household income. In Winchester, the home price to income ratio is 6.8, which is 15.3% higher than the Massachusetts average.

Best Places to Live in and Around Winchester

See all the best places to live around Winchester

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Compare Winchester, MA Livability

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      Winchester transportation information

      Statistic Winchester Massachusetts National
      Average one way commute34min29min26min
      Workers who drive to work66.8%71.1%76.4%
      Workers who carpool6.2%7.5%9.3%
      Workers who take public transit10.5%9.9%5.1%
      Workers who bicycle0.9%0.8%0.6%
      Workers who walk1.2%4.9%2.8%
      Working from home14.1%4.7%4.6%
      Source: The Winchester, MA 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.