2026 Compare Cities Overview:
Winter Garden, FL vs Oakland, FL

Are people in Oakland older or younger than people in Winter Garden?
- The Median Age in Oakland is 1.6 years younger than in Winter Garden.

Are housing costs cheaper in Oakland or Winter Garden?
- Oakland housing costs are 3.8% less expensive than Winter Garden housing costs.

Which city has a longer commute, Oakland or Winter Garden?
- The average commute for residents of Oakland is 2.4 minutes shorter than it is for residents of Winter Garden.

Things to do in Winter Garden?
Winter Garden, Florida is a city located in Orange County. The city offers a variety of shops and restaurants, as well as outdoor activities such as golfing and hiking.

Things to do in Oakland?
Living in Oakland, FL is a great experience for those who love the outdoors. With its lush, rolling hills and beautiful lakes, Oakland is a perfect spot for outdoor recreation. Whether you are looking to go boating or fishing on the lake, take a hike in one of the many nearby parks or simply soak up the sunshine while taking in the stunning scenery, Oakland is sure to leave you with plenty of memories. The city also offers plenty of shopping and dining opportunities as well as entertainment venues that can be enjoyed year-round. With its charming neighborhoods and friendly neighbors, it’s easy to see why so many people choose to call Oakland home.