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Life course-informed theories of development suggest it is important to integrate information about positive and negative aspects of the social environment into studies of child and parental wellbeing, including both stressors that compromise health and resources that promote well-being. We recruited a sample of 169 pairs of caregivers and young children (birth to 5 years) from a community health clinic and administered survey questions to assess stressors and resources. We constructed inventories of stressors and resources and examined the relationships between these inventories and caregivers’ depressive symptoms, anxiety symptoms, and sleep problems, and young children’s medical diagnoses derived from electronic health records. Cumulative stressors and resources displayed bivariate and adjusted associations with caregivers’ depressive symptoms, anxiety symptoms, and sleep problems. For depressive and anxiety symptoms, these associations were evident in models that included stressors and resources together. Caregivers with high stressors and low resources displayed the highest levels of depressive and anxiety symptoms and sleep problems. In terms of children’s health outcomes, only modest trends were evident for developmental/mental health outcomes, but not other diagnostic categories. Future studies are needed to examine stressors and resources together in larger samples and in relation to prospectively assessed measures of child well-being.