ABSTRACT In 2020, a coalition formed between a local real estate developer, a nonprofit, and a senator soon to run for state governor, with the goal of turning a never-used county jail in Portland, Oregon, into a homeless shelter. Reading with abolitionist anthropologist Savannah Shange’s concepts of “progressive dystopia” and “carceral progressivism,” this paper is a case study of Wapato Jail’s redevelopment into the Bybee Lakes Hope Center, serving as an in-depth look at how Portland’s localized real estate state utilizes the logics of “carceral progressivism” to maintain the city as a dystopia that works for them [Shange, S. (2019). Progressive dystopia: Abolition, anti-blackness, & schooling in San Francisco. Duke University Press]. Utilizing data from archival materials, news media, and twenty interviews, I argue that the real estate state, composed of local developers with long-standing stakes in the city, form alliances in an attempt to shift the provision of services away from a Housing First approach and to maintain the city in a state of “just crisis enough” to keep growing profits and property values. Cutting across abolitionist and carceral geographies, I present an engagement with the maintenance and growth of carcerality within the real estate state, particularly as elites get involved with homeless services.