Population ageing has become a domain of international discussions and research throughout the spectrum of disciplines including housing, urban planning, and real estate. Older people are encouraged to continue living in their homes in their familiar environment, and this is referred to as “ageing-in-place”. Enabling one to age-in-place requires new housing arrangements that facilitate and enable older adults to live comfortably into old age, preferably with others. Innovative examples are provided from a Dutch social housing association, illustrating a new approach to environmental design that focuses more on building new communities in conjunction with the building itself, as opposed to the occupational therapeutic approaches and environmental support. Transformation projects, referred to as “Second Youth Experiments”, are conducted using the Røring method, which is based on the principles of co-creation. De Benring in Voorst, The Netherlands, is provided as a case study of an innovative transformation project. This project shows how social and technological innovations can be integrated in the retrofitting of existing real estate for older people. It leads to a flexible use of the real estate, which makes the building system- and customer preference proof.