Due to social stigma, lack of social support, and minimal legal employment opportunities, transgender women (transwomen) face elevated rates of unstable housing. This study examined the association between housing status and HIV risk behaviors among 517 transwomen encountered through street outreach. Seven variables (including sociodemographics, HIV status, housing status, and sexual partner type) were used to estimate partial associations during multivariable analyses; housing status was coded trichotomously (housed, marginally housed, and homeless) for these analyses. Results demonstrated that homeless and marginally housed transwomen engaged in significantly higher rates of illicit drug use than housed transwomen; however, marginally housed and housed transwomen engaged in significantly higher rates of illegal hormone injections than homeless transwomen. Rates of sex work were high in the sample as a whole, though sex with an exchange partner was most common among the marginally housed transwomen. Multivariate logistic regression revealed that unstable housing moderated the association between HIV status and engagement in unprotected serodiscordant anal intercourse. The marginally housed transwomen exhibited the greatest risk profile for HIV acquisition or transmission.