The proportion of older people is increasing. During the years lived with disease and functional mobility loss, ensuring their well-being becomes a challenge for society. In addition to health, well-being in old age depends on various circumstances of an individual’s personal life. While contact with family members from a distance or irregular contact may be sufficient for satisfying the need for communication and may alleviate loneliness, it cannot replace the assistance that being present can provide. The difficulties or disadvantages are associated with some types of living arrangements. Therefore, patterns of living arrangements for older people are of key importance in studies of their well-being.The demographic characteristics vary by country but differences are expected to be less between societies experiencing a similar path in development. Since the last decade of the 20th century, rapid changes have brought Eastern Europe closer to the more developed areas of Europe, both in economic and social terms. The patterns of living arrangements for older people in Estonia compared to people of similar age in Belgium show some signs of convergence, the latter being considered representative of Western Europe. The studied period for Estonia includes the transition period from the Soviet regime to the current situation. Accordingly, we address the question of whether this transition accounts for some specific features in Estonia, compared with Belgian trends. We find rather different patterns in the distribution of older people’s living arrangements in the two countries but similar trends in the changes indicating convergence between the two countries.