This study explores the relationships between acculturation and health behaviors among low-income housing residents, and examines whether these relationships are mediated by social and contextual factors. The fact that acculturation may influence health behaviours is known, yet the mechanisms underlying its effect have not been much explored so far. A composite acculturation scale was developed using latent class analysis, resulting in four distinct acculturative groups, and 828 residents in the Boston metropolitan area completed surveys that assessed acculturative characteristics, social/contextual factors, and health behaviors. Path analysis was used to examine interrelationships between acculturation, health behaviors, and social/contextual factors, specifically self-reported social ties, social support, stress, material hardship, and discrimination. 69% of the people interwieved were born outside of the U.S. Less acculturated groups exhibited healthier dietary practices and were less likely to smoke than more acculturated groups. Acculturation had a direct effect on diet and smoking, however not on physical activity. Acculturation also showed an indirect effect on diet through its relationship with material hardship. Our finding that material hardship mediated the relationship between acculturation and diet suggests the need to explicate the significant role of financial resources in interventions seeking to promote healthy diets among low-income immigrant groups. Future research should examine these social and contextual mediators using larger, population-based samples, preferably with longitudinal data.