2025 Compare Cities Overview:
Windermere, FL vs Chesapeake, VA

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Highlights
Are people in Chesapeake older or younger than people in Windermere?
- The Median Age in Chesapeake is 15.8 years younger than in Windermere.

Are housing costs cheaper in Chesapeake or Windermere?
- Chesapeake housing costs are 47.9% less expensive than Windermere housing costs.

Which city has a longer commute, Chesapeake or Windermere?
- The average commute for residents of Chesapeake is 0.8 minutes shorter than it is for residents of Windermere.

Things to do in Windermere?
Living in Windermere, FL is an experience like no other. With its idyllic atmosphere and close proximity to numerous attractions, you will never be bored here. It's the perfect combination of suburban life with a taste of Southern hospitality. The weather is typically sunny and warm, with temperatures remaining moderate year-round. Plus, you can enjoy stunning views of Lake Down and the surrounding green spaces while strolling around town. There's something for everyone in Windermere; you can shop at nearby malls or spend time outdoors kayaking or fishing on the lake. Whether you're looking for a quiet place to call home or an exciting adventure, Windermere has it all!

Things to do in Chesapeake?
Chesapeake, Virginia is a vibrant city known for its beautiful scenery and bustling downtown. Enjoy the temperate climate while exploring its attractions such as outdoor trails, lakeside beaches, shopping centers, delicious restaurants and various entertainment venues. With its excellent shopping centers, lively nightlife and cultural events happening throughout the year, Chesapeake is sure to provide something to keep everyone entertained!

 Windermere, FLChesapeake, VAUnited States
 Population  Unlock247,172329,725,481
 Median Income$131,392  Unlock$69,021
 Median Age  Unlock37.138.4
 Avg. Home Price$689,100  Unlock$338,100
 Unemployment Rate  Unlock5.0%6.0%
 Avg. Commute Time26.65  Unlock26.38
Reviews for Windermere    3 Reviews

I moved to Windermere from Chicago and I am having a difficult time adjusting here. Sure, the weather is great, but everything else is not. I have to drive for long  More

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Windermere, Florida is home to many top athletes and famous people including Tiger Woods & Shaq O'Neil. This is a quaint little town that guards itself against too much  More

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Over 16 years ago

I've spent the last 5 years in Windermere Fl. and 31 years in the state of Florida. Windermere is a small town set amongst the Butler Chain of Lakes. It has it's older  More

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Reviews for Chesapeake    33 Reviews

I lived here in Virginia near the Cedar Rd. not so far from Tidewater Community college. If you want a great place to live to raise children, its Chesapeake  More

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I live around this area currently, in the "Hampton Roads". Which consists of Virginia Beach, Suffolk, Norfolk, Portsmouth, Newport News, Hampton, and Chesapeake. We're  More

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I was born in Hampton Roads and lived there for more than 65 years. We lived in the city of Chesapeake for three years from 2014-2017. Frankly, we were very glad to  More

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