In colonial America, land acquired new liquidity when it became liable for debts. Though English property law maintained a firm distinction between land and chattel for centuries, in the American colonies, the boundary between the categories of real and personal property began to disintegrate. There, the novelty of easy foreclosure and consequent easy alienation of land made it possible for colonists to obtain credit, using land as a security. However, scholars have neglected the first instances in which a newly unconstrained practice of mortgage foreclosure appeared—the transactions through which colonists acquired land from indigenous people in the first place. In this article, I explore these early transactions for land, which took place across fundamental differences between colonists' and native communities' conceptions of money, land, and exchange itself. I describe how difference and dependence propelled the growth of the early American contact economy to make land into real estate, or the fungible commodity on the speculative market that it remains today.