The rise and crash of the Roman villa system reads eerily like the modern story of American foreclosures-profit schemes of land speculation, securitized, and excessively mortgaged. Where did this process of suburbanizing the rural hinterlands begin? I propose to interrogate the rise of the villa, the first suburban experiment, to inform our understanding of modern landscapes of speculation. Poorly defined in common lore, Roman-era villas actually consumed large swaths of landscape, far more expansive than their well-studied architecture. As sprawling, army-supplying agricultural complexes, they colonized the empire from Palestine to Britain. By probing their origin in and near Rome, along with parallels to the current crisis, I hope to reveal some of modern civilization's latent tendencies to speculate on landscape futures. Perhaps peeling apart this synergy of leisure, speculation, and profit in Roman villas can reformat our current landscape speculative practices.