Over the past decade, real estate developers continued to build new housing in cities that were losing population. This articulates a seeming paradox: If former residents are leaving a place, what drives developers and investors to continue to build new housing? Population loss is hardly a rare occurrence in the United States, and although many American cities have experienced decline, the phenomenon of new housing in shrinking cities remains understudied. Toledo, Ohio, offers an archetypal Rust Belt setting where new housing continues to be built, even though Toledo has lost population both at the city and regional levels for decades. This thesis presents an in-depth case study exploring the degree to which demographic change, the provision of new housing types not found elsewhere in the market, and the spatial redistribution of regional employment inform developers’ decision to pursue a market-rate residential project. The thesis further interrogates the role of image-making, marketing, and public-sector investment within broader economic development efforts to retain and attract educated younger adults to Toledo. Interviews with real estate developers and allied practitioners provide insight into the everyday experience of pursuing and justifying new housing in the context of a shrinking city. Ultimately, the thesis aims to draw out lessons from Toledo that developers, investors, and public officials in other shrinking localities can apply to inform their policy-making and investment decisions.