This chapter examines the challenges of the concept of aging in place in environment that itself ages, where the physical infrastructure deteriorates as residents grow older. Through one Hong Kong public housing estate and two Shanghai lilong communities, this chapter explores how environmental decline, historical legacies, and social change shape older adults’ well-being. Employed with mixed methodologies, the findings indicate that across these three cases, physical upgrades alone are insufficient. Effective aging in aging places requires innovative and creative integrated strategies that combine inclusive design, community supports, cultural heritage sensitivity, and meaningful resident participation. The joint effort and interdisciplinary approach can theoretically enhance a sense of identity, belonging, and control among the elderly residents, yet cannot neglect the intrinsic uneven urban landscapes shaped by gentrification, inequality, displacement, and environmental risk. Policies must institutionalize participatory, transgenerational, and socially embedded approaches facilitated by advanced artificial intelligence to ensure equitable and dignified aging in a rapidly aging population in a rapidly transforming urban environment.