There are substantial differences in work organization between residential and commercial construction sectors. This paper examined differences in work factors between construction sectors and examined the association between sector and health behaviors, health outcomes, and work outcomes. We surveyed 929 male construction apprentices (44% residential and 56% commercial) and found that residential apprentices reported fewer workplace safety policies, higher frequency of heavy lifting, and greater likelihood of reporting musculoskeletal pain compared to apprentices in commercial work. Residential apprentices reported higher job strain, lower supervisor support, more lost workdays due to pain or injury, and lower productivity related to health than commercial apprentices. Multivariate Poisson regression models controlling for multiple work factors showed that residential construction work, high job strain, heavy lifting, low coworker support, and low supervisor support were each independently associated with one or more work or health outcomes. These findings suggest that interventions should seek to improve coworker and supervisory supportive behaviors, decrease job strain, and reduce organizational stressors, such as mandatory overtime work. Our study shows disparities in health and safety between construction sectors and highlights the need for interventions tailored to the residential sector.