Abstract: Homelessness and chronic disease have been previously linked. We examined the bidirectional, sex-specific, relationship between homelessness and cerebrovascular disease among aging veterans seeking U.S. Department of Veterans Affairs (VA) healthcare services. A retrospective study was conducted among a cohort of 4,061,031 veterans (mean [± standard deviation] age: 68.7 [± 10.3] years; 94.6% men) followed between 2017 and 2021 and defined through linkage of VA Corporate Data Warehouse, Homeless Operations Management System, and Mortality Data Repository databases. Multivariable Cox regression models were constructed to bidirectionally examine associations between the first episode of homelessness and the first cerebrovascular disease event by sex. Multistate modeling was applied to examine sex differences in transitions from a healthy state to death through homelessness and cerebrovascular disease, adjusting for confounders. Overall, the earliest homelessness episode and earliest subsequent cerebrovascular disease event were negatively associated (hazard ratios (HR) = 0.30 [95% confidence intervals (CI): 0.29, 0.32]) among the 4,057,313 veterans who did not experience cerebrovascular disease before homelessness. Conversely, the earliest non-fatal hemorrhagic stroke event and earliest subsequent homelessness episode were positively associated (HR = 1.13, 95% CI: 1.04, 1.24) among the 4,059,465 veterans who did not experience homelessness before cerebrovascular disease. Female veterans were less likely than male veterans to transition from a healthy state to homelessness, stroke, or death. Irrespective of sex, veterans who experience homelessness may be less likely to be later diagnosed with cerebrovascular disease, while those who experience non-fatal hemorrhagic stroke may be more likely to later experience homelessness.