Barrons’ Twenty Best Places to Buy a Second Home: Lake Geneva, Wisconsin

For second homes in America’s most affluent locations, the past year was ugly. No way else to describe it. Median home prices were down 50% in North Lake Tahoe, and 44% on Martha’s Vineyard, to cite two examples.

Last year was brutal for second homes in the nation’s most affluent areas. But the market is firming up again. Here’s our list, expanded to 20 sites, for those seeking top-tier refuges.

Lake Geneva has long been called the Newport of the West because 19th-century Chicago industrialists, such as the Wrigleys, Swifts and Montgomery Wards, built their 20-room “summer cottages” on the grassy shores of the crystal-blue lake that inspires the town’s name. The lakeside imperial lawns are still dotted with Tudor, Italianate and French chateau mansions of that era. Chicago investor Richard Driehaus’ annual summer soirees require so much temporary staff (one year it featured a circus theme replete with a baby elephant) that the money manager becomes the largest employer in town.

The Grand Geneva Resort a few miles off the lake is the former Playboy Club where Hugh Hefner once retreated. Today, many prefer Chuck’s Lakeshore Inn, where you might bump into a CEO in boat shoes or an NBA star. Until recently, an Italian steakhouse in town bore the name of the Milwaukee Brewers’ star Ryan Braun; he has a house nearby and managed last year to be the National League’s Most Valuable Player and to overturn a suspension for alleged performance-enhancing drug use. Lake Geneva deal of the year: Michael Keefe, one of the area’s top real-estate agents, sold his own home for $5.9 million in 2011.

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