Milwaukie Way reconsiders the potential for an urban infill development to respond to its context, creating a lively public space while also preserving the existing built fabric. Sited on a central commercial avenue in a popular neighborhood in Southeast Portland, the clients wanted the new building to engage with passing shoppers and maximize the potential value of the site. They imagined 7,300 square feet of new leasable space for a combination of cafe, boutique retail, and offices. Complicating this ambition, an existing 1929 Spanish Colonial-style building sat in the center of the lot, greatly limiting the available street frontage for the new development. The challenge became how to balance the needs of the new building with the integrity of the historic structure, while increasing the possibilities of public engagement across the site. Our approach was to avoid competing with or demolishing the old building and instead physically pull the proposed buildings back from the lot frontage, extending the activity of the street into the site through a new pedestrian alleyway. Choosing to embrace and highlight the existing site elements, two new buildings were developed as quiet and complimentary backdrops to the existing building’s stucco and terracotta. Clad in vertically ribbed black metal, these structures are punctuated by a consistent pattern of six-foot wide window and door openings that appear cut from their dark textured surfaces to create a ribbon-like effect. Exterior corners are rounded to further enhance the appearance of a continuous, uninterrupted surface. Internally, the building provides flexible spaces that nonetheless have distinct character. Support functions, such as bathrooms, stairs, and mechanical equipment, are grouped in a central core allowing the retail and office spaces to have exposed floor and roof structures. The exposed “ribbed” wood joist ceilings on each level give the open spaces richness and texture. Bridging between new and old, the scale of the alleyway is reminiscent of Old World streets, providing a vibrant environment for neighborhood gathering, interaction, and chance meetings. This shared space simultaneously maximizes the potential retail frontage of the new buildings, while providing more engagement with the existing building. The result is an approach to development that both graciously accommodates the requested program of the client, while also protecting and reinvigorating the existing structures and neighborhood.