2025 Compare Cities Cost of Living:
Windermere, FL vs Winnetka, IL

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Highlights
Is it cheaper to live in Winnetka or is it cheaper to live in Windermere?
- Winnetka is 0.3% less expensive than Windermere.

Which city has more affordable housing, Winnetka or Windermere?
- Winnetka housing costs are 149.4% more expensive than Windermere housing costs.

Is Health Care more affordable in Windermere or is Health Care more affordable in Winnetka.
- Health related expenses are 14.9% less in Winnetka.
 Windermere, FLWinnetka, ILUnited States
 Overall  Unlock105.7100
 Food & Groceries106.9  Unlock100
 Health  Unlock88.0100
 Housing177.8  Unlock100
 Median Home Cost  Unlock$1,348,300$338,100
 Utilities103  Unlock100
 Transportation  Unlock140.5100
 Miscellaneous107.1  Unlock100
100 = National Average (Below 100 means cheaper than the US average. Above 100 means more expensive.)
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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 Winnetka    2 Reviews

Having had children attend both public and private schools. I would say the private schools are better. While the public schools are fine, there isn't any way to measure  More

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This idyllic, leafy, close-in suburb north of Chicago comes straight out of a Frank Capra (or John Hughes - see Home Alone for a view of the housing stock and  More

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