Architectural space has long played an important role in the human imaginary, whether in art, horror, and uncanny fiction, or in the subconscious realm of dreams. But what place do the aesthetics of contemporary architecture hold in the collective and personal imagination? Can modern single bedroom apartments and suburban track houses offer settings for identity creation and the idyllic home? In this thesis, an artist traces these questions in the context of a body of paintings inspired by a life-long fascination with architectural space. These pieces are discussed along with the technical process and formal decisions behind their creation. Several pertinent concepts are researched and discussed in relation, including a comparison of architectural movements, philosophy, repression, nostalgia, and the uncanny.