2026 Compare Cities Cost of Living:
Middletown, DE vs Winchester, VA

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Highlights
Is it cheaper to live in Winchester or is it cheaper to live in Middletown?
- Winchester is 12.0% less expensive than Middletown.

Which city has more affordable housing, Winchester or Middletown?
- Winchester housing costs are 28.4% less expensive than Middletown housing costs.

Is Health Care more affordable in Middletown or is Health Care more affordable in Winchester.
- Health related expenses are 7.9% less in Winchester.
 Middletown, DEWinchester, VAUnited States
 Overall  Unlock91.6100
 Food & Groceries108.3  Unlock100
 Health  Unlock103.6100
 Housing141.0  Unlock100
 Median Home Cost  Unlock$332,900$338,100
 Utilities109  Unlock100
 Transportation  Unlock83.1100
 Miscellaneous112.0  Unlock100
100 = National Average (Below 100 means cheaper than the US average. Above 100 means more expensive.)
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Reviews for Middletown    4 Reviews

Over 13 years ago

Housing in Middletown is abundant and affordable. There are townhomes and single family homes. There are very small lots to large farmettes available right now. A major  More

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Over 15 years ago

.... I could leave Delaware  More

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Over 18 years ago

Outdoor recreation is very limited here. There are very few parks with walking trails in Middletown. The state parks are beautiful, but it seems that very few people  More

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Reviews for Winchester    17 Reviews

I have lived in Winchester for 13 years and I find the locals to be rude, unpleasant and loud. Women worse than men... that's not to say all is bad, the city has some  More

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Over 10 years ago

Worst place I have ever lived. My neighbors hate jemmy since I am not a clone. They do not respect other people's property.I put up a fence and the same day the  More

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I would have to say I agree with much of what another individual wrote: it's like going back in time or living in a place that refuses to adapt to cultural diversity.   More

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