This study attempted to model important factors that influence subjective well-being (SWB) of the middle-aged and older people in Taiwan, including extraversion, neurotic personality and social support. Multi-samples structural equation model technique was used to investigate the differences between the middle-aged and older people in structural model coefficients. A convenience of sample of 640 participants, 45-95 years of age with a mean age of 61.05 was recruited in Taiwan. There were 296 participants with age 60 and above who were categorized into the older people group. The remaining 344 participants were categorized into the middle-aged group. In general, extraversion personality had significant positive effects on social support and SWB; neurotic personality had significant negative effects on social support and SWB; social support had significant positive effects on SWB. In contrast to the middle-aged people, older people’s social support had an increasing effect on SWB. Four structural paths were found to be non-significant, including the decreasing negative effects of neurotic personality on social support and SWB, the decreasing positive effect of extraversion personality on social support, and the increasing effect of extraversion personality on SWB. Despite the nonsignificant findings, the increasing effect of extraversion on SWB remains important for future research attention.