Emerging research suggests that prolonged sedentary behaviour (SB) is detrimental to health. Changes in SB patterns are likely to occur during particular life stages, for example at retirement age (55–65-year-old). Evidence on socio-ecological SB correlates is scarce and inconsistent in this age group. Moreover, the influence of socio-ecological correlates may vary depending on health and retirement status. This study examined social and environment correlates of overall weekend day sitting among adults at or approaching retirement age, and moderating effects of perceived physical health and retirement status. Baseline data from the Wellbeing, Eating and Exercise for a Long Life study in 2839 Australian adults (55–65-year-old) were analysed. Participants self-reported proximal social factors, neighbourhood social and physical environment, physical health and retirement status. MLwiN multilevel regression analyses were conducted. In the multivariable model, only social support from friends/colleagues to discourage sitting (B = −0.891; p = 0.036) was associated with overall weekend day sitting. No moderation of retirement status, nor physical health were found in the multivariable results. Results from this study suggest the importance of social factors in relation to weekend day sitting among 55–65-year-old adults. Health promotion initiatives in this age group should pay special attention to enhancing social interaction opportunities. Moreover, findings suggest that SB-specific correlates may need to be examined in future research.