2025 Compare Cities Overview:
Westport, CT vs Winchester, MA

Are people in Winchester older or younger than people in Westport?
- The Median Age in Winchester is 3.7 years younger than in Westport.

Are housing costs cheaper in Winchester or Westport?
- Winchester housing costs are 15.9% less expensive than Westport housing costs.

Which city has a longer commute, Winchester or Westport?
- The average commute for residents of Winchester is 8.6 minutes shorter than it is for residents of Westport.

Things to do in Westport?
Westport, CT is a town located along the Long Island Sound. It's known for its scenic shoreline, upscale shopping, and history of being home to some of the most influential figures in American media and arts. Westport also boasts some of the best public schools in the state making it an attractive residential option for many families.

Things to do in Winchester?
Winchester is a lovely suburban town located just 8 miles north of Boston in Middlesex County Massachusetts. Serving as home to some of New England’s oldest homes Winchester Center is a great place to explore history while also benefiting from access to Boston’s cultural assets. This well ranked school district also offers families plenty of educational opportunities as well.