This study was premised on the idea that baby boomers, like anyone else, desire to maximize their well-being. That is, they seek situations that provide positive emotion, engagement, relationships, meaning and accomplishment (PERMA) which determine their personal appraisal of well-being based on both objective and subjective measures. Thus, the purpose of the research was to identify the most important PERMA elements of well-being that the baby boomer cohort who have decided to retire but have not yet done so (i.e., pre-retirees), seek in their preference in post-retirement residence. Moreover, this study investigates the degree to which this group sees that choice being influenced by their affinity for technology. The data for this correlational study was collected through a survey instrument administered to respondents electronically. The responses were analyzed utilizing logistic regression to generate research findings and implications. The results of this study suggest there is a relationship between the PERMA elements of well-being, singly and collectively, and their preference in post-retirement residence. Further, when considering the impact of affinity for technology on these two variables, the hypothesis of moderation was not significant. Lastly, the impact of Coronavirus (COVID-19) on baby boomers’ preference in post-retirement residence was also considered. Future research in these areas is warranted as technological innovations continue to impact the delivery of the elements of well-being, and as baby boomers move through their retirement years, to consider the potential impact on their preference in post-retirement residence.