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

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

Are housing costs cheaper in Westport or Winchester?
- Westport housing costs are 18.9% more expensive than Winchester housing costs.

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

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.

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.