Sleep debt is associated with presenteeism and mental health; however, the association of sleep debt with presenteeism and well-being in the context of work-related social factors (commuting time, workdays, and working hours) has not been fully elucidated. This study aimed to examine whether work-related social factors are associated with presenteeism and well-being via sleep debt. The participant group comprised 872 full-time and 526 part-time workers (mean age: 44.65 ± 12.37 and 48.47 ± 12.93 years, respectively). For both the full-time and part-time workers, increased sleep debt was significantly associated with presenteeism (β = −0.171; β = −0.160) and low well-being (β = −0.135; β = −0.153). Notably, commuting time was significantly associated with increased sleep debt in full-time workers (β = 0.09). In contrast, the number of workdays was significantly associated with increased sleep debt in part-time workers (β = −0.102). Working hours were not significantly associated with sleep debt for both full- and part-time workers. These results reveal that sleep debt might lead to various risks among workers, elucidating the work-related social factors related to sleep debt. They also highlight the importance of considering work-related social factors when addressing sleep debt.