Although retirement ages are rising in the United Kingdom and other countries, the average number of years people in England can expect to spend both healthy and work from age 50 (Healthy Working Life Expectancy; HWLE) is less than the number of years to the State Pension age. This study aimed to estimate HWLE with the presence and absence of selected health, socio-demographic, physical activity, and workplace factors relevant to stakeholders focusing on improving work participation. Data from 11,540 adults in the English Longitudinal Study of Ageing were analysed using a continuous time 3-state multi-state model. Age-adjusted hazard rate ratios (aHRR) were estimated for transitions between health and work states associated with individual and combinations of health, socio-demographic, and workplace factors. HWLE from age 50 was 3.3 years fewer on average for people with pain interference (6.54 years with 95% confidence interval [6.07, 7.01]) compared to those without (9.79 [9.50, 10.08]). Osteoarthritis and mental health problems were associated with 2.2 and 2.9 fewer healthy working years respectively (HWLE for people without osteoarthritis: 9.50 years [9.22, 9.79]; HWLE with osteoarthritis: 7.29 years [6.20, 8.39]; HWLE without mental health problems: 9.76 years [9.48, 10.05]; HWLE with mental health problems: 6.87 years [1.58, 12.15]). Obesity and physical inactivity were associated with 0.9 and 2.0 fewer healthy working years respectively (HWLE without obesity: 9.31 years [9.01, 9.62]; HWLE with obesity: 8.44 years [8.02, 8.86]; HWLE without physical inactivity: 9.62 years [9.32, 9.91]; HWLE with physical inactivity: 7.67 years [7.23, 8.12]). Workers without autonomy at work or with inadequate support at work were expected to lose 1.8 and 1.7 years respectively in work with good health from age 50 (HWLE for workers with autonomy: 9.50 years [9.20, 9.79]; HWLE for workers lacking autonomy: 7.67 years [7.22, 8.12]; HWLE for workers with support: 9.52 years [9.22, 9.82]; HWLE for workers with inadequate support: 7.86 years [7.22, 8.12]). This study identified demographic, health, physical activity, and workplace factors associated with lower HWLE and life expectancy at age 50. Identifying the extent of the impact on healthy working life highlights these factors as targets and the potential to mitigate against premature work exit is encouraging to policy-makers seeking to extend working life as well as people with musculoskeletal and mental health conditions and their employers. The HWLE gaps suggest that interventions are needed to promote the health, wellbeing and work outcomes of subpopulations with long-term health conditions.