Within the framework of the life trajectory paradigm, factors of poor health in older age may include ethnicity, as well as migration history of an individual. Estonia, with a large share of the Russian population, is a good example to analyze the impact of migration and changes in the ethnic environment on health throughout the life course. The purpose of the study is to assess differences in self–rated health of the older population (50+) living in Estonia and Russia, and identify reasons for these differences. The empirical basis of the study was data of the SHARE survey conducted in Estonia in 2010-2011 and the SAGE survey conducted in Russia in 2007-2010. The sample includes urban population aged 50+ in private households: 2,655 Estonians living in Estonia, 1,478 Russians living in Estonia, and 2,446 Russians living in Russia. The tested ordinal regression models show that the native-born in Estonia have a 39% higher chance of rating their health as good compared to Russians in Estonia, which is associated with differences in educational level in the population aged 50-64, while in the population aged 65+ it is associated with differences in living standards between the native-born and immigrants of the first and subsequent generations. At the same time, Russians from Russia are 70% (population aged 50-64) or 60% (population 65+) less likely to rate their health as good, which is related to the lifestyle and loneliness. Russians aged 65+ in Estonia who moved to the country at the age of 25+ have the same chances. The study negatives the healthy migrant effect identified in young immigrants, and also indicates health behavior and poor quality of social connections as possible reasons for poor health of the older Russian residents.