Mitt Romney spent the first five years of his life in Detroit's Palmer Woods neighborhood, before his family decamped to the ultra-wealthy suburb of Bloomfield Hills. Romney's first house has not survived Detroit's efforts to fight blight, as it was demolished in 2009 after falling into disrepair.

The home where a young Romney spent his formative years, it sits on a street that has been very generous to the former Governor's campaign. Once at the center of a much larger tract, the land has since been parceled off.

Home to the Romney clan during Mitt's tenure as Massachusetts governor, this brick mansion sits on a densely treed and private lot in the tony Boston suburb of Belmont. The Romneys owned the historic '30s spread for more than two decades before unloading it for $3.5M in 2009.

Purchased for upwards of $2.5M, this New Hampshire lake house has been in the Romney portfolio since 1997, and the addition of a neighboring parcel has upped the value to $10M. A 5,400-square-foot stone-and-shingle lodge is the highlight of the property, which also includes stables, tennis courts, and a guest house.

By the time Romney was running the 2002 Winter Olympics in Salt Lake City, he had just completed construction on this sprawling ski lodge in the mountains of Park City. Sited on nearly 11 acres, with sweeping views of the valley, it sold in 2009 for around $5.2M.

Probably the most famous of Romney's homes is this oceanfront spread in La Jolla. Purchased in 2010 for $12M, the existing 3,000-square-foot home will be expanded to more than 11,000 square feet and is set to include the infamous $55K car elevator.

After years as a fixture on the Chicago political scene, Obama settled on this brick mansion as a permanent home for his family—at least until he was swept into the White House in 2008. The Obamas paid $1.65M for the Georgian manor, which was built in 1910 and features "four fireplaces, glass-door bookcases fashioned from Honduran mahogany, and a 1,000-bottle wine cellar."

Prior to purchasing their current home, the Obamas bought and sold a four-bedroom condo in Chicago's Eastview Park condominium community. The ground floor unit, sold by the Obama for $415K in 2005, rented in 2010 for $2,400 per month.

After transferring from Occidental College to Columbia University, Obama moved into this modest two-bedroom flat near the school on Manhattan's Upper West Side. Thirty years later, the place was up for rent again, this time for $2,400 per month.

Set on an exclusive and secluded peninsula in Kailua, Hawaii, this is the rental house where Barack Obama and his family have spent each Christmas since his inauguration. The 6,900-square-foot pad goes for $4,000 per night in high season, and rumor is the Secret Service take up residence in the surrounding houses.

Like many presidents before him, Obama chose preppy Martha's Vineyard as a summer getaway from the pressures of the White House. Of course, the house he rented was hardly modest. Known as Blue Heron Farm, the 28.5-acre estate was sold last year to starchitect Norman Foster for a whopping $22M.