2025 Compare Cities Overview:
Winchester, MA vs Oakland, CA

Are people in Oakland older or younger than people in Winchester?
- The Median Age in Oakland is 5.5 years younger than in Winchester.

Are housing costs cheaper in Oakland or Winchester?
- Oakland housing costs are 33.9% less expensive than Winchester housing costs.

Which city has a longer commute, Oakland or Winchester?
- The average commute for residents of Oakland is 1.2 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 Oakland?
Oakland, California is the vibrant city at the heart of the Bay Area. With its beautiful parks and nature preserves, lively nightlife scene, and booming arts and music scene, there’s something for everyone in this diverse and thriving city. Visitors can explore historical landmarks like Jack London Square or take a stroll through Chinatown. The city also offers plenty of outdoor activities including kayaking on Lake Merritt or hiking through Redwood Regional Park. With its bustling atmosphere, great cultural attractions and countless outdoor experiences to choose from, Oakland is sure to make any visit an unforgettable one!