Limited data indicates that homelessness during pregnancy is linked to adverse outcomes for both mothers and newborns, but there is an information gap surrounding pregnant individuals struggling with homelessness. In a landscape of increasing healthcare disparities, housing shortages and maternal mortality, information on this vulnerable population is fundamental to the creation of targeted interventions and outreach. The current study investigates homelessness as a risk factor for adverse obstetrical, neonatal, and postpartum outcomes. We reviewed more than 1000 deliveries over 1year at a large public hospital in New York City, comparing homeless subjects to a group of age-matched, stably housed controls. Multiple outcomes were assessed regarding obstetrical, neonatal, and postpartum outcomes along with social stressors. Homeless pregnant individuals were more likely to experience numerous adverse outcomes, including cesarean delivery and preterm delivery. Their neonates were more likely to undergo an extended stay in the intensive care unit and evaluation by the Administration for Children's Services, suggesting that they may be at an increased risk for family separation. After delivery, patients were less likely to exclusively breastfeed or return for their postpartum visit. Regarding personal history, they were more likely to endorse a history of violence or abuse, use illicit substances, and carry a psychiatric diagnosis. These findings indicate that homelessness is linked to numerous adverse obstetrical, neonatal, and postpartum outcomes that worsen health indices and exacerbate pre-existing disparities. Initiatives must focus on improved outreach and care delivery for homeless pregnant individuals.