2026 Compare Cities Cost of Living:
Windermere, FL vs Leesburg, FL

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Highlights
Is it cheaper to live in Leesburg or is it cheaper to live in Windermere?
- Leesburg is 5.0% less expensive than Windermere.

Which city has more affordable housing, Leesburg or Windermere?
- Leesburg housing costs are 59.4% less expensive than Windermere housing costs.

Is Health Care more affordable in Windermere or is Health Care more affordable in Leesburg.
- Health related expenses are 2.1% less in Leesburg.
 Windermere, FLLeesburg, FLUnited States
 Overall  Unlock100.7100
 Food & Groceries106.9  Unlock100
 Health  Unlock101.2100
 Housing177.8  Unlock100
 Median Home Cost  Unlock$291,300$338,100
 Utilities103  Unlock100
 Transportation  Unlock85.1100
 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 17 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 Leesburg    4 Reviews

My city sits between Lakes Harris and Griffin as part of the St. John's river system it helped the city grow.Now we rest between the two top growing communitys in  More

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Due to poor wages for the working class most people have to work two jobs this includes both husband and wife therefore children lack supervision so the crime rate is  More

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Nice little town surrounded by lakes. Great if you are retired as the majority of the population is 60+. This is largely driven by The Villages (largest retirement  More

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