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Background: Few studies have assessed the mental health of principals, or studied associations with both organizational and social work environment factors and occupational balance. The purpose of the present study was therefore to investigate associations between supporting and demanding organizational and social work environment factors, occupational balance and stress symptoms in principals. Methods: A total of 4309 surveys (2316 from the first round, 1992 from the second round), representing 2781 Swedish principals who had responded to at least one of two surveys, were included in the present study. The surveys include questions about socio-demographic factors, occupational balance, overtime work, and supporting and demanding organizational and social work environment factors, as well as questions about personal stress and exhaustion. Generalized Estimating Equations (GEE) models were used to specify a repeated measures model with a dichotomous outcome (binary logistic regression) and multiple independent factors. Data from two surveys were combined, taking into account dependent observations due to the fact that many study subjects had participated in both surveys. Results: Associations were found between occupational balance (Q1: OR 2.52, 95% CI 2.03–3.15; Q2: OR 4.95, 95% CI 3.86–6.35; Q3: OR 9.29, 95% CI 6.99–12.34), overtime work (Once a week: OR 1.51, 95% CI 1.10–2.08; Sometimes a week: OR 1.31, 95% CI 1.03–1.66), supportive private life (OR 1.50, 95% CI 1.36–1.66), supportive colleagues at the leadership level (OR 1.24, 95% CI 1.14–1.36), supportive management (OR 1.17, 95% CI 1.07–1.28) and no or negligible stress symptoms. In addition, role demands (OR 0.72, 95% CI 0.63–0.83), having a container function (OR 0.72, 95% CI 0.64–0.82), collaboration with employees (OR 0.77, 95% CI 0.66–0.89), role conflicts (OR 0.75, 95% CI 0.66–0.89) and having a buffer function (OR 0.86, 95% CI 0.77–0.97) were associated with lower likelihood to rate no or negligible stress symptoms. Conclusions: The occupational balance of principals is strongly associated with no or negligible stress symptoms, and thus is a promising venue for promoting well-being. Improvements should be made to several factors in the organizational and social work environments to improve principals’ chances of having occupational balance, and therefore better mental health.