Over fall term 2022, Community and Regional Planning graduate students worked with the City of Sisters to design a research based redevelopment proposal for the Sisters Elementary School and Sisters School District administration building site. Students analyzed potential opportunities and challenges of revitalizing these two adjoining properties through three different lenses: 1) age friendly neighborhoods; 2) adaptive reuse of preexisting structures, and 3) a community and recreation center. Despite different focus areas, as the teams moved through the planning process, they sought to incorporate what they understood to be community values: connection, livability, accessibility, equity, and safety. With their focus areas and these values in mind, they organized their proposals around the overarching themes of connectivity, built spaces (especially housing), and open and green spaces. The teams imagined the site in a way that would sustain Sisters’ strong sense of pride and community as the city continues to grow in the future. They also wanted to encourage healthy lifestyles for Sisters’ residents and ensure that people of all ages, incomes, and abilities could access the site safely. This report describes the information that the teams gathered and analyzed to create their designs, details each team’s site proposal, and offers ideas for implementation.