Houses are lifetime investments for many. For majority of us, we can’t shop around for better ones all the time. Families change in time and as do family’s needs. Houses age, and require updating. Some people would chose to demolish the existing or move to a different new house. However, building upon the existing is one solution that is more sustainable and perhaps better than other alternatives if it can be accommodated but the users. How should designers tackle introducing new insertion into the existing site and building to achieve good outcomes for the client? This project aims to find best possible solution for the client by embrace the existing condition, regulations, and client’s needs while keeping the existing and the new insertion bringing together the new and old with simplicity and functionality. This project has been developed through site visits, many discussions, multiple iterations, drawings, renderings and critiques. The project proposal includes two alternative solutions. First option uses the full width of the site, where the new addition is built to the site boundary. This provides opportunity for the client for large open plan family area as well as large semi-covered exterior area creating a transition space between interior and exterior. Second option is perhaps a more neighbour friendly proposal. The semi-covered exterior area wraps around the open family area. The interior become smaller, but offers clients opportunity to have smaller exterior pocket deck adjacent to the kitchen. Having two alternative helps the client with negotiating through regulations and approval process. This proposal offers a solution to the client where the new insertion works well with the existing building fabric yet gaining plenty of space to accommodate for their growing needs.