This essay surveys the many, contradictory links between private ownership and human flourishing and assesses the moral implications of this complexity. It begins with and ultimately broadens claims made by leading South African scholars on the need to reconsider longstanding ways of thinking about property, particularly the “rights paradigm.” Private ownership in obvious ways benefits an owner. But as explained, the links between private rights and human flourishing are far greater, implicating not just owners but neighbors, surrounding communities, the landless, future generations, and other life forms. The recognition of private property rights can both expand and curtail human flourishing. As for human flourishing, it is equally complex in that it is affected by many factors going far beyond physical needs. Property rights are created by law and involve the use of state power to protect rights by curtailing the liberties of non-owners and others. The only sound moral justification of this use of coercive power — this use of state power to help owners control and dominate others — rests in the ways a well-designed property regime can foster the welfare of nearly everyone, owners and non-owners alike. Law thus should not vest an owner with any power that does not, on balance, promote widespread human flourishing. Inherited ways of thinking about private property cloud these realities and distort inquiries into property’s origins and moral and practical consequences. Much of this thought is best wiped away with discussion begun from a new place, from an express recognition of private property as an evolving, socially created, morally complex institution that can both promote and undercut human flourishing, an institution that must be carefully calibrated to maintain its moral legitimacy and maximize its social benefits.