Healthcare workers’ age is increasingly rising, negatively affecting their physical health. In particular, workability is an emerging phenomenon that predominantly affects healthcare workers. This study aims to assess physical health status and workability among ageing healthcare workers. A cross-sectional study using the Work Ability Index (WAI) was performed. Data were collected in a university hospital in northern Italy. Data were collected voluntary through a questionnaire. Healthcare workers participating in the survey were contacted personally by two resident physicians. Thus, the total number of study participants was 220 among nursing aides, nurses, and physicians. Data were analyzed by performing ANOVA and regression to assess the differences between the healthcare workers and age groups. A generalized linear model was tested to evaluate the effect of age and task on workability. The majority of healthcare workers had good WAI values. Physicians’ workability was higher than nursing aides. Nursing aides suffered more from cardiovascular disorders, while physicians and nurses had more musculoskeletal disorders. However, the distribution was statistically different (χ2 = 24.03, p = 0.00), as most of the physicians’ workability values were good and good, while those of nursing aides and nurses were good and medium. In line with previous studies, the decrease in WAI with ageing is strictly dependent on the type of task assigned. Due to heavy physical tasks, nurses and nurses’ aides showed a greater WAI than physicians. This study highlights the critical issues faced by ageing healthcare professionals. In the near future, it is necessary to find solutions to cope with these changes and devise possible interventions aimed at ameliorating workability.