Who knew indie movie icon, ironic Republican, and enemy of Roger Ebert Vincent Gallo could also negotiate multimillion dollar real-estate deals in his spare time?

In July 2006, Gallo purchased the John Lautner-designed Wolffe House in the Hollywood Hills—an insanely modern work of art in wood, stone, and glass—for just under $4 million. Now, with the staggering asking price of $5.9 million, he stands to clear a nearly $2 million dollar profit in less than one year.

And it's hardly his first purchase and sale of architecturally significant property. He recently sold a one-bedroom apartment at the Sierra Towers in West Hollywood (formerly owned by David Geffen) to Cher for close to $4.5 million. He's also owned a couple of apartments in the much ballyhooed Richard Meier buildings on Manhattan's West Side.

Click for a full tour of Gallo's Hollywood property!