The purpose of the present study was to investigate the decision-making process and outcomes associated with downsizing to a smaller home in late life. Using Wiseman’s behavioral model of elderly migration, participants’ reasons for moving (push factors) and reasons for selecting the new residence (pull factors) were explored. It was hypothesized that the relation between push-pull factors and relocation outcomes would be serially mediated by control and sense of place (SOP). Self-report measures of reasons for moving, relocation controllability, SOP, satisfaction with the move, and psychological well-being were examined in a sample of 68 older adults (mean age 72.7 years) who had downsized to a smaller home in the past year. Haye’s PROCESS macro was used to test serial multiple mediator models for each of the relocation outcomes (i.e., satisfaction with the move and six subscales of well-being). Results showed that placing greater importance on push relative to pull factors was associated with lower levels of well-being in three domains: environmental mastery, purpose in life, and self-acceptance. Although SOP discrepancy (i.e., SOP in current versus previous home) was not a significant mediator, the serial mediation model with relocation controllability and current SOP as mediators was significant for move satisfaction, environmental mastery, and personal growth. This suggests that older adults whose downsizing decisions are more strongly influenced by push factors feel less control over relocation, find it more difficult to develop a SOP in the new home, and, in turn, experience lower levels of well-being and relocation satisfaction. These findings can be used to inform older adults’ downsizing decisions and to develop supports for relocating older adults.