#5. Washington Island, WI
Median home value: $187,200
Not all islands are balmy. This one is cool — in both senses of the word! About 700 people live year-round on this island that’s north of the tip of Wisconsin’s Door County Peninsula. The Washington Island Ferry provides year-round service to Washington Island for both passengers and vehicles (there are 100 miles of paved roads on the island).
The island is full of museums, plus it has its very own performing arts center and a fiber arts school that teaches knitting, weaving and basketry. On Saturday during the summer, you can browse the local farmers market, or venture to the lookout tower that rewards you with panoramic views of the island and beyond — after you’ve climbed 186 steps.