Background: Chronic obstructive pulmonary disease (COPD) and heart failure (HF) are chronic diseases that impart significant health and care costs to the patient and health system. Limited access to health services affects disease severity and functional status. Telemonitoring has shown promise in reducing acute care utilization for chronic disease patients, but the benefit for the underserved has not been determined. We evaluated acute care utilization outcomes following an acute event of a 90-day transitional care program integrating telemonitoring technology and home visits for underserved COPD and HF patients. Materials and Methods: Patients were enrolled into the program between October 2010 and August 2012. Primary outcomes included rates of emergency department (ED) visits and all-cause re-admission at 30, 90, and 180 days postdischarge. Program and functional status at enrollment and discharge and satisfaction with telemonitoring at discharge were measured. Telemonitoring included daily symptomatology recording and was removed at 90 days. A control cohort was identified through electronic health records and propensity-matched via 15 variables to achieve a sample size with balanced baseline characteristics. Results: Program patients showed 50% reduction in 30-day re-admission and 13–19% reduction in 180-day re-admission compared with control patients. There was no significant difference in ED utilization. Patients were satisfied with telemonitoring services, and functional status improved by program end. Conclusions: This feasibility study suggests telemonitoring in the context of a transitional care model following an acute event may reduce all-cause 30-day re-admissions by up to 50% and has the potential to reduce longterm acute care utilization and thus care costs. More rigorous and long-term investigation is warranted.