This study aimed to investigate the prevalence and trajectories of chronic diseases and risk behaviors in immigrants from high-income countries (HIC), low–middle-income countries (LMIC), to Australian-born people. Data were used from five waves of the HABITAT (2007–2016) study—11,035 adults living in Brisbane, Australia. Chronic diseases included cancer, diabetes mellitus, coronary heart disease, and chronic obstructive pulmonary disease (COPD). Risk factors assessed were body mass index (BMI), insufficient physical activity, and cigarette smoking. Diabetes mellitus increased in all groups, with the highest increase of 33% in LMIC immigrants. The prevalence of cancers increased 19.6% in the Australian-born, 16.6% in HIC immigrants, and 5.1% in LMIC immigrants. The prevalence of asthma increased in HIC immigrants while decreased in the other two groups. Poisson regression showed that LMIC immigrants had 1.12 times higher rates of insufficient physical activity, 0.75 times lower rates of smoking, and 0.77 times lower rates of being overweight than the Australian-born population. HIC immigrants had 0.96 times lower rates of insufficient physical activity and 0.93 times lower rates of overweight than Australian-born. The findings of this study can inform better strategies to reduce health disparities by targeting high-risk cohorts.