This essay explores the contingent relationships between landownership and status in Britain, the Caribbean, and the East Coast of North America across the long eighteenth century. In Britain, where land was scarce, land was the measure of wealth and status, and the creation of landed estates bound the ruling elite together. As the global economy expanded, driven by colonialism, new relationships were embedded within very different cultural landscapes. In the Caribbean, plantation landscapes were high-risk investments that relied on enslaved labor to ensure returns on highly capitalized production. In America, the availability of land recast the relationship between improvement, landownership, and labor. Land played an important role in defining newfound freedoms increasingly at odds with coercion and enslavement.