Obama's home Barack Obama While Obama did spend part of his childhood in Hawaii before moving to Chicago, he owns just one home in the Windy City. He and wife Michelle bought the brick home in 2005 for $1.65 million (shown below). Located on Greenwood Avenue, the home, pictured above, was built in 1917 and offers 6,199 square feet of space. Mitt Romney The former governor of Massachusetts owns a smattering of real estate across the country, including homes in Massachusetts, California and New Hampshire. This collection has been pared down; Romney previously owned two other homes a large estate in Belmont, MA that he sold for $3.5 million in 2009 and a ski home in Park City, UT that he also dumped in 2009 for a little over $5.25 million. Mitt-Romney-La-Jolla-house. When Romney is not on the campaign trail, his main home is in the beachfront town La Jolla (shown below). Romney and his wife, Ann, purchased the $12 million La Jolla home in 2008, telling reporters he wanted to be somewhere he could hear the waves. Apparently a home on the high-priced California coast, (median La Jolla home values hit $1,186,200), was the right location. Mitt Romney townhouse In June 2010, the Romneys bought a 2-bedroom townhouse in suburbanBelmont (shown right). According to property listing information, the Romneys paid $895,000 for the 2,100-square-foot home in the new residential development The Woodlands. This is the first purchase the Romneys have made in the Massachusetts area in two years; previously they claimed their sons basement apartment as their legal address. Romney Wolfeboro The Romneys own an 11-acre property (shown right) smack dab on the shores of Lake Winnipesaukee in Wolfeboro. Purchased for $3 million in 1997, the Romneys 5,400-square-foot main house and additional guest houses are home to the extended Romney family each summer.