This article was given as the 6th Annual Wolf Family Lecture on the American Law of Real Property, University of Florida Levin College of Law (2013). It draws on property law discussions in Richard R.W. Brooks and Carol M. Rose, Saving the Neighborhood: Racially Restrictive Covenants, Law, and Social Norms (Harvard Univ. Press 2013). The article outlines the ways in which constitutional law and property law engaged in a dialog about white-only racial covenants from their early twentieth-century origins to the middle of the twentieth century and beyond. After a shaky beginning, both constitutional law and property law became relatively permissive about racial covenants by the 1920s. But proponents of racial covenants had to work around property law doctrines — including seemingly arcane doctrines like the Rule Against Perpetuities, disfavor to restraints on alienation, "horizontal privity," and "touch and concern." Moreover, property law weaknesses gave leverage to civil rights opponents of covenants, long before Shelley v. Kraemer (1948), the major constitutional case that made these covenants unenforceable in courts. Even after Shelley's constitutional decision, property law continued to be a contested area for racial covenants, with echoes even today.