The rising prevalence of chronic diseases could be mitigated by expanding community programs. This study aimed to evaluate the feasibility of delivering a community wellness program for older adults living with chronic disease. A two-group randomized controlled study, with blinded assessments, enrolling adults (≥50 years) with chronic disease, was conducted at a Western Australian community hub. Participants randomly allocated to the intervention participated in exercise groups and a wellness activity twice a week. Both the intervention and control groups received a Fitbit™ and workbook. The primary outcomes were recruitment, retention, acceptability, and suitability. The secondary outcomes measured at baseline and 12 weeks included physical function and physical activity (step count). There were 126 older adults approached, of whom 22 (17.5%) were recruited. Eighteen participants (mean age = 70.8 ± 8.1, n = 8 intervention, n = 10 control) completed 12 weeks. Two intervention participants (25% adherence) completed over 70% of sessions and eight participants (44.4% retention) accepted an ongoing 3-month program. Health problems (30.2%) were barriers to both recruitment and adherence. There were no significant between-group differences in physical function. Physical activity was significantly higher in the intervention group compared to the control group (p = 0.01). Tailored programs with ongoing support may be required to improve the health of older adults living with chronic disease.