The owners of this 100-year-old house hired 9.SQUARE and Landscape Architect Andy Masterpole (of Yaggy Colby Associates) to modify their site design to accommodate a more gentle sloping driveway, new 2-car garage, and mud room addition onto the rear of the house. Our approach was one of both functionality and aesthetics to create a brand new layout that was more compatible with a modern family paradigm while blending into the historic architecture. We also created an abundance of outdoor entertaining space of different scales that was more private. The driveway now has a more manageable 9% slope that flattens out behind a small privacy fence with stone piers that match the limestone foundation. Beyond, the driveway is a combination of pavers and colored concrete to double as outdoor parking area and large outdoor event space. The garage sits high at the rear of the site to shield a private sunken patio on the north side of the house with a cedar deck pergola that creates a datum connecting garage to mud room. The design is a holistic approach to entrance, parking, privacy, and entertaining, with materials and style to be consistent with the existing structure.