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The Midwestern Martha's Vineyard, From Pioneers to Millionaires

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Today, the lakeside town of Okoboji, Iowa is a place for rest and relaxation, a pricey summer getaway for midwesterners who want to stay close to home. It wasn't always that way. In 1857, the town was the site of clashes between settlers and the indigenous Sioux Indians which resulted in the so-called "Spirit Lake Massacre." The settlers were persistent, however, and by 1860 occupied a permanent settlement on the lake. By the turn of the century, the borough had turned from a rough and tumble frontier town to a resort community with the construction of an inn. In 1917, a lumber baron by the name of Franklin Floete built this 32-room mansion (above), a testament to the sort of tribes Okoboji had begun to attract.

? The region keeps the legacy of that massacre close to the surface, despite the transition to a fun-loving vacation getaway. An amusement park, now known as Arnolds Park, was built not far from the site of the massacre in 1917. The park (above) drew the crowds and the surrounding lake was soon ringed by large lake houses for those who wanted to spend the entire summer by the lake—or wailing away on the wooden roller coaster. The popularity of this summer escape is still going strong, with a generational following that packs out the township from May to August.

WHAT'S ON THE MARKET NOW:

? Built in 1929, The Hacienda is one of Okoboji's classic estates, with the photos to prove it. Lately, the four bedroom seems to have fallen into disrepair, with the property being marketed as a house or a building lot. A teardown would be a sad fate for this $2.85M diamond in the rough, but, with 230 feet of waterfront, the temptation might be too great.

? Further down the same street, Lakeshore Drive, this 1994 build has the wood-frame construction of a quintessential lake house, but with more bells and whistles than one might expect—well, before a glimpse at the price tag anyway. Outdoor entertaining space galore, six bedrooms, a boathouse and attached three-car garage drove the price up to $2.5M.
? Those looking to go all out on a midwestern lake house would be well-served by this $2.9M offering in nearby Spirit Lake. Built in 2006, the 9,000-square-foot manse offers six bedrooms and an ever-so-woodsy timber-frame construction, but the next owner will have to make do with, boo hoo, just 84 feet of lake frontage.

· History [City of Okoboji]
· 4703 Lakeshore Drive [IDX]
· 7005 Lakeshore Drive [IDX]
· 17204 Ross Road [IDX]