The COVID-19 pandemic limited older adults’ access to preventative and diagnostic services and negatively affected accessibility to age-appropriate exercise programs. The purpose of this study was to assess the feasibility of conducting guided virtual functional fitness assessments before and after participation in an 8-week virtual, live fitness program (Vivo) designed for older adults. It was hypothesized there would be no significant difference between in-person and virtual functional fitness assessments and function would improve following the program. Thirteen community-dwelling older adults were recruited, screened, and randomly assigned to in-person-first or virtual-first fitness assessment groups. Validated assessments were delivered using standardized scripts by trained researchers and included Short Physical Performance Battery (SPPB) balance, a 30 s Chair Stand Test, 8 Foot Up-and-Go Test, 30 s Arm Curl Test, and 2 min Step Test. The eight-week, twice-a-week live virtual fitness program involved cardiovascular, balance, agility, Dual-Task, and strength training. Results showed no significant differences between all but one assessment measures, and several measures improved following the eight-week program. Fidelity checks demonstrated the high fidelity of program delivery. These findings illustrate that virtual assessments can be a feasible method to measure functional fitness in community-dwelling older adults.