2025 Compare Cities Overview:
Winchester, MA vs Brookline, MA

Are people in Brookline older or younger than people in Winchester?
- The Median Age in Brookline is 7.1 years younger than in Winchester.

Are housing costs cheaper in Brookline or Winchester?
- Brookline housing costs are 17.2% less expensive than Winchester housing costs.

Which city has a longer commute, Brookline or Winchester?
- The average commute for residents of Brookline is 3.6 minutes shorter 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 Brookline?
Brookline, Massachusetts is a charming town located in Norfolk County. This vibrant community offers a wealth of attractions and activities for all ages, from its historic landmarks and neighborhoods to its variety of parks and recreational areas. There are plenty of things to do in Brookline, whether you're looking for an outdoor adventure or a night out on the town. With its diverse range of shops, restaurants, museums, and entertainment venues, Brookline is an excellent destination for those seeking culture and relaxation. Whether you're visiting with family or friends, Brookline is sure to provide many memorable experiences!