Condoland casts CityPlace – a massive residential development of more than thirty condominium towers just outside Toronto’s downtown core – as a microcosm of twenty-first-century urban intensification that has transformed the city skyline beyond all recognition. Built almost entirely by a single private developer, this immense neighbourhood took decades to plan, design, and develop, but the end result lacks a sense of place and is not widely accessible to those who need homes: only a fraction of its 13,000 units constitute affordable housing, and public amenities are limited. Casting an eye toward the frantic vertical urbanization of Toronto, Condoland traces the forty-year history of the city’s largest residential megaproject. James T. White and John Punter summarize the tools used to shape Toronto’s built environment and critically explore the underlying political economy of planning and real estate development in the city. Using detailed field studies, interviews with key actors, archival research, and with nearly two hundred illustrations, White and Punter reveal how a promise to reproduce Vancouverism, a celebrated model of Canadian urban development, unravelled under an alarmingly flexible approach to planning and design that is acquiescent to the demands of a rapacious development industry. Through a uniquely design-focused evaluation of a phenomenon increasingly known as “condo-ism,” Condoland raises key questions about the sustainability and long-term resilience of city planning.