Empirical evidence suggests that the stability of personality itself contributes to successful ageing and is associated with longer life. The aim of this study was to investigate the association between personality traits and the self-perceived health status, stratified by medical conditions in a representative sample of non-institutionalized elderly people in Chile. The data used for this study come from the fourth waves (2009) of the Chilean Social Protection Survey (SPS-2009). Included were a total of 2655 subjects aged 65 and over. The results showed that higher scores of all five personality factors were associated with good health. Those with the perception of poor health were more likely to be female, with lower education level and older than those with good health. With the exception of agreeableness, strong and significant associations with self-perceived health were demonstrated for extraversion, conscientiousness, emotional stability and openness, among elderly with medical conditions. Among elderly without medical problems, significant associations with self-perceived health were demonstrated only for extraversion, agreeableness and emotional stability. This study has shown that there is a consistent association between personality factors and self-perceived health throughout the older population. Our results suggest that extraversion and openness traits could be acting as “protector” factors and agreeableness and conscientiousness traits as “resilient” factors, facing to the health problems among elderly people.