Senior housing communities have been exploring ways to create opportunities for different generations to interact and bond, with the goal of enhancing the level of care they provide for their residents. This study looks at two such initiatives: Bridge Meadows in Portland, Oregon, an intergenerational housing community; and Friendsview Retirement Community in Newburg, Oregon, a senior housing community with multiple intergenerational programs. The former is a budding initiative that is picking up popularity as it includes foster youth, whereas the latter is a more traditional approach that offers intergenerational programs by linking up with universities, and community organizations such as cultural and fitness centers. Secondary analysis is utilized to explore the two initiatives on three major dimensions: design, service and community, enabling me to gauge the challenges and impact of these programs. The study also examines the similarities and differences between intergenerational communities and intergenerational programs in senior housing communities, highlighting the importance of collaborations from various organizations and individuals in such initiatives. By comparing these two unique initiatives, this study also outlines future implications on design, programming and policy levels for designers, planners, local governments, and multiple stakeholders.