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10 Things to Know Before Moving to Winchester, MA

Written by Aislyn Hobbs

Situated eight miles outside of Boston proper, Winchester is a quaint little suburb town surrounded by rivers and lakes. Since the majority of Winchester residents drive to work, the town offers a tranquil escape from the city’s constant noise and traffic. 

Due to its location in one of the original American colonies, Winchester boasts a history that dates back to 1640. After becoming an official town over two centuries later, Winchester blossomed into the idyllic suburb it is today.

Here are ten things to know before moving to Winchester, Massachusetts.

1. There’s a small percentage of youths

Winchester is far more rural and dispersed than Boston, which has a much denser population (22,875 vs. 3,800/km²). Expect a slightly older population here, with a median age of 42, as is typical in suburbs. 

Due to the small percentage of the population between the ages of 20 and 39, you may have difficulty meeting other people in your generation if you are in your twenties or thirties. But when it comes to the remaining population, the age distribution is very uniform. While whites make up 82% of Winchester’s population, there is also a sizable Asian minority, accounting for 13% of the total.

2. The cost of living in Winchester is 74% higher than the national average

Being a wealthy neighborhood adjacent to one of the most costly cities in the US, it’s no surprise that Winchester can have a very steep cost of living. The high cost of housing in Winchester accounts for the majority of the 74% cost of living premium compared to the rest of the country. A house in Winchester can be yours for an average price of $1,386,958. There are a lot of rental options in Winchester, and the average monthly rent is $3,600.

Everything else, like groceries, transportation, and utilities, will be more expensive than the national average, but typically only by 10% to 20%.

3. One of the safest cities in America

Winchester is among the safest cities in America, and that’s saying a lot! With a total of 3 crimes per 1,000 people, Winchester has one of the lowest crime rates in the United States among cities of any size (less than 84% of America’s cities). 

The violent crime rate is 8.8, while the property crime rate is 15.2. If you’re looking to live in a city where your safety is almost guaranteed, Winchester is your best bet.

4. The Winchester School District serves the city

Whether you’re a parent or a student, living in Winchester gives you access to some of the nation’s top schools and colleges. There are several excellent public schools in the Winchester School District, which mostly serves the residents of Winchester. 

Your younger children will thrive at the contemporary, widely recognized Vinson-Owen Elementary and McCall Middle Schools, and your adolescent will thrive on the magnificent Winchester High School campus.

5. Harvard University and Massachusetts Institute of Technology are only minutes away

Are you relocating to Winchester and worried about the availability of suitable universities for your older children or yourself? If you still have any reservations, you may put them to rest knowing that Winchester is close to illustrious educational institutions.

It goes without saying that Harvard University is a world-class institution. It is 17 minutes (7.3 miles) away from Winchester. The public four-year institution Boston College is renowned for its excellence and rigorous academic requirements. It’s only 24 minutes (11.0 miles) away.

The prestigious Massachusetts Institute of Technology, or MIT for short! MIT is highly regarded and holds high standards in the field of education. MIT is 9 miles away. 

6. It rains and snows a lot in Winchester

With an average high of 83 degrees Fahrenheit in the summer, this city enjoys pleasant weather. However, winters can drop to 16 degrees Fahrenheit, and there is far more precipitation in Winchester than the national average. 

Winters in Winchester are chilly and rainy, with 53 inches of snow yearly and 47 inches of rain. You can count on about 200 days of sunshine and about 135 days with rain or snow. Bring along something warm to keep you cozy!

7. Work in the healthcare or education sector

Winchester is conveniently located near a major American commercial center. No matter what industry you’re targeting, Winchester has plenty of job opportunities!

If you are looking for a high-paying job in this area, you should know that the healthcare industry is a fantastic choice, especially for roles like operating room nurse, pharmacy technician, and registered nurse. Jobs such as public school teachers, law clerks, and university professors also tend to pay the most.

8. The Museum of Bad Art is a must-see

The founders of MoBA had a different vision from what is expected of a typical art museum, which would display high-quality works of art. Gathering and exhibiting some of the most repulsive works of art since 1994, the Museum of Bad Art has become a popular destination for art lovers and haters alike. 

Make sure you stop by the Museum of Bad Art in Winchester if you’re in need of some self-esteem boost or simply some laughs!

9. Take the kids to the Beanstalk Adventure Ropes Course

You might not expect to find Beanstalk in a furniture store, but that doesn’t change the fact that it is one of the most popular attractions in Winchester! 

Beanstalk Adventure Ropes Course is an odd yet entertaining addition to Jordan’s Furniture Store, with a two-story, long rope course with a height of 12 and 24 feet, respectively. 

The BeanSprout course, perfect for children ages 2 to 7, is also a part of this attraction. Among Winchester’s many family-friendly attractions, Beanstalk Adventure stands out.

10. Eat at China Sky, Ristorante Lucia, or A Tavola

Winchester is not only home to wonderful attractions, but it is also a culinary mecca!

Looking to satisfy your sweet taste and consume gingerbread outside of the holiday season? Lucky you if you call Winchester home! You can trust the Gingerbread Construction Company with all of your custom gingerbread needs.

The best Chinese and Japanese chefs in the state get together at China Sky to create a wide variety of mouth-watering delicacies that are true to real Chinese and Japanese cuisine. China Sky is the place to go in Winchester if you’re an Asian foodie who can’t get enough!

The authentic Italian fare and delightful, old-world decor of Ristorante Lucia make it a must-visit. Popular items on their extensive menu include chicken parmesan and fried calamari. Everyone from families to couples looking for a night out can find what they’re looking for at this friendly restaurant, which is a local favorite.

At A Tavola, you can find delicious Italian cuisine prepared using seasonal, locally sourced ingredients. From appetizers to main courses, their varied menu offers it all, from a selection of handmade pasta to the irresistible porchetta.


Winchester, MA, offers a peaceful retreat from Boston, with a rich history since 1640. While it has an older population and a high cost of living, it stands out as one of the safest cities in America. 

Proximity to top schools, job opportunities, cultural attractions, and culinary delights add to its charm. In essence, Winchester provides a unique living experience with a blend of history, safety, education, and cultural diversity.

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