This dissertation investigates how online platforms such as Airbnb, Reddit, and Craigslist reflect and shape contemporary housing dynamics within American urban regions. It features three papers that each analyze user text data within these platforms through a combination of natural language-based machine learning modeling with qualitative reviews of user's written contributions. The first chapter examines how Airbnb hosts employ rhetoric to commodify their short-term rentals in reference to cultural narratives relevant to neighborhood gentrification and residential exclusion. The second study explores how Reddit users debate about regional housing by drawing on policy frames to justify their arguments and persuade other users. The third paper considers how landlords posting advertisements for rentals on Craigslist use the intentional delineation of move-in fee financial requirements to influence the behavior of prospective tenants. These three papers collectively delineate how behaviors regarding three distinct housing subjects- neighborhood cultural change, housing policy debates, and rental market searches- are now conducted within online platforms. Results across the three studies demonstrate how user interactions on these sites reinforce preexisting housing dynamics and inequalities regarding unit availability and affordability at both the individual household and metropolitan level. These findings emphasize how longstanding sociocultural understandings of housing are now reinforced within these emergent online communities. The dissertation additionally illustrates how a mixed-methodological framework combining computational tools with subjective interpretation of text data is an ideal approach for answering research questions relevant to the intersection of urban housing and digital platforms. All three chapters engage with policy implications relevant to their individual findings, and the dissertation concludes by considering its overarching applicability for future research, applied data science initiatives, and towards contemporary urban housing governance.