The physical and societal characteristics of home have been established as important in influencing the health and wellbeing of older adults, yet these have rarely been explored together. There is also limited research into variation across age groups, with older adults often examined as a homogenous group of those 65 years and over. This study advances the knowledge base by using the concept of person–environment (P-E) fit to analyse differences in personal and home environment (physical and societal) characteristics between young-old (65–74 years) and old-old (75 and above) age groups, and to assess how these characteristics influence their self-perceived health. This cross-sectional study draws upon survey data from 1,999 older adult participants from the Australian Housing Conditions Dataset. Descriptive statistics and inferential analysis were used to assess for significant differences between age groups and a binomial logistic regression was utilised to examine influences on health. The analysis found that the factors which influence health varies appreciably between age groups. For the young-old financial strain, being on the fixed-income pension and hypertension were important contributing factors, in contrast for the old-old gender (being male), having depression and the home being modified for disability were key influences. For both age groups heart disease was a contributing factor to perceived health. The results indicate the important contribution to knowledge of incorporating a wide range of person and environment characteristics when exploring P-E fit for older adults. The inclusion of societal aspects, such as financial strain, fixed-income pension, tenure and access to community aged care services when exploring influences on health, arises as a key conclusion of the study. In terms of impact, this research is significant given rising inequalities globally and specifically in the Australian context, the need for policy measures to address income inequality, and its health and social implications for older households.