This article explores various relationships between the elderly's psychosocial well-being and components of aging-friendly community (continuity, compensation, connection, challenge, and contribution), in order to understand their perception of a matured estate and to discuss implications in housing neighborhood urban design. Interviews with elderly residents living in Bukit Merah (Redhill), one of the matured housing estates in Singapore with a high percentage of elderly residents, were conducted to understand how eldercare infrastructure and social spaces developed within the fabric of a high-rise, high-density public housing estate can support or inhibit their psychosocial well-being, as indicated by the Geriatric Depression Scale (GDS). Our results postulate that different groups of elderly form friendships and participate in activities in both formal social service centers and informal public spaces. The friendships formed in these places and the convenience of amenities around their houses may affect their perception of their current residences. While the elderly residents are generally satisfied with physical infrastructure, a comprehensive, integrated urban design is further needed to facilitate physical activities, social interactions, and active aging in the elderly in order to enhance their psychosocial well-being.