This paper explains how history, economics, public policy, and culture have combined to make Tokyo a city full of microspaces and how those microspaces shape Tokyo’s land use possibilities. Today’s Tokyo is a “new” city, having been largely rebuilt from scratch after wartime devastation, and its land use is deeply shaped by that history. As for regulation, Japan’s combination of hierarchical zoning and progressive taxation policies encourage an entirely different mix of land use in Tokyo’s urban core than what is found in most American cities. Tokyo’s postwar profusion of small landowners coexists in tension with its major corporate conglomerates, which combine real estate development with commuter railway infrastructure and consumer businesses on a scale unheard of in the United States. When ambiguities and disputes regarding land use arise, in practice they are mediated outside of courtrooms by local citizen-governance bodies and the powerful yet under-resourced Tokyo police, both of which play a unique role in these communities. By exploring these countervailing forces and explaining the mix of formal and informal actors shaping them, this paper aims to help policymakers, researchers, and activists in America’s cities better understand what lessons can (and cannot) be drawn for American urban policy from Tokyo’s microspaces.