2025 Compare Cities Cost of Living:
Shepherdstown, WV vs Winchester, VA

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Highlights
Is it cheaper to live in Winchester or is it cheaper to live in Shepherdstown?
- Winchester is 17.6% less expensive than Shepherdstown.

Which city has more affordable housing, Winchester or Shepherdstown?
- Winchester housing costs are 20.2% less expensive than Shepherdstown housing costs.

Is Health Care more affordable in Shepherdstown or is Health Care more affordable in Winchester.
- Health related expenses are 16.9% less in Winchester.
 Shepherdstown, WVWinchester, VAUnited States
 Overall  Unlock91.6100
 Food & Groceries107.5  Unlock100
 Health  Unlock103.6100
 Housing126.4  Unlock100
 Median Home Cost  Unlock$332,900$338,100
 Utilities89  Unlock100
 Transportation  Unlock83.1100
 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 Shepherdstown    4 Reviews

Over 12 years ago

Beautiful and mostly  More

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Over 14 years ago

Shepherdstown has been my home for 25 years since I was a teenager and the people are wonderful and friendly! I love Shepherdstown and I am proud to call it my  More

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Over 14 years ago

We bought our vacation home in this quaint, historic town and are loving the time we spend there. The nearby Potomac river is beautiful and offers canoeing and kayaking  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 9 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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