Background The high prevalence of chronic diseases, including congestive heart failure (CHF), chronic obstructive pulmonary disease (COPD), and diabetes mellitus (DM), accounts for a large burden of cost and poor health outcomes in US hospitals, and home telehealth (HT) monitoring has been proposed to improve outcomes. Objective To measure the association between HT initiation and 12-month inpatient hospitalizations, emergency department (ED) visits, and mortality in veterans with CHF, COPD, or DM. Design Comparative effectiveness matched cohort study. Patients Veterans aged 65 years and older treated for CHF, COPD, or DM. Main Measures We matched veterans initiating HT with veterans with similar demographics who did not use HT (1:3). Our outcome measures included a 12-month risk of inpatient hospitalization, ED visits, and all-cause mortality. Key Results A total of 139,790 veterans with CHF, 65,966 with COPD, and 192,633 with DM were included in this study. In the year after HT initiation, the risk of hospitalization was not different in those with CHF (adjusted odds ratio aOR 1.01, 95% confidence interval 95%CI 0.98–1.05) or DM (aOR 1.00, 95%CI 0.97–1.03), but it was higher in those with COPD (aOR 1.15, 95%CI 1.09–1.21). The risk of ED visits was higher among HT users with CHF (aOR 1.09, 95%CI 1.05–1.13), COPD (1.24, 95%CI 1.18–1.31), and DM (aOR 1.03, 95%CI 1.00–1.06). All-cause 12-month mortality was lower in those initiating HT monitoring with CHF (aOR 0.70, 95%CI 0.67–0.73) and DM (aOR 0.79, 95%CI 0.75–0.83), but higher in COPD (aOR 1.08, 95%CI 1.00–1.16). Conclusions The initiation of HT was associated with increased ED visits, no change in hospitalizations, and lower all-cause mortality in patients with CHF or DM, while those with COPD had both higher healthcare utilization and all-cause mortality.