Background/Objectives: People experiencing homelessness (PEH) face greater morbidity, multimorbidity, and premature mortality than the general population. Medical data on this population in Gdańsk remain scarce. The aim of this study was to assess the prevalence, age distribution, comorbidity burden, and healthcare utilization of selected neurological and vascular diseases among homeless men in Gdańsk, Poland. Methods: A retrospective secondary analysis was performed using data from 551 men residing in shelters operated by the largest PEH support organization in Gdańsk. A random sample of 226 individuals (95% confidence level) was analyzed, selected by randomization in Microsoft Excel. Data were extracted from interviews, verified medical documentation, and staff records. Results: Mean age was 57.0 (SD 12.9) years (median 60). Among the studied sample, essential (primary) hypertension (20.4%), heart failure (10.2%), atrial fibrillation (8.9%), and chronic obstructive pulmonary disease (8.4%) were the most common conditions. Sequelae of cerebrovascular disease (ICD-10: I69) affected 8.9% of participants; this subgroup was older and had higher rates of disability certification and hospitalization than the overall sample. Epilepsy (12.0%) and polyneuropathy (4.0%) differed in age distribution, disability rates, and comorbidity burden, with the epilepsy subgroup displaying high substance-use prevalence. Overall, 44.0% of the sample had been hospitalized since 2019. Conclusions: Homeless men in Gdańsk present a high burden of neurological and vascular disease at comparatively young ages, along with substantial multimorbidity. These findings highlight structural inequalities in healthcare access and the need for integrated, equity-oriented health and social care interventions.