This research explores some of the first cases of intergenerational living in London; Buccleuch House, the ‘Lifecycle Home’ in Chobham Manor, and Supportmatch UK Homesharing. The cases are studied through a number of themes, ranging from the motivation behind engagement in intergenerational living, the benefits and drawbacks of such a living arrangements, the design of intergenerational schemes, and the viability of intergenerational developments for the mainstream housing market. The experiences of key stakeholders involved in the intergenerational schemes are cross compared, with the aim of gaining a holistic understanding of the recent emergence of intergenerational living in London, focusing on the forms it can take, its design and development, and its’ future prospects. This research works towards a body of literature that promotes ways in which diversity can be encouraged in urban planning and offers inspiration in how this can be done. Furthermore, the topic bares great relevance to the debate sparked by the COVID-19 pandemic surrounding housing and healthcare, and especially that of older generations. Findings indicate that although becoming a more heavily debated topic, making frequent appearances in government policy and planning discourse, intergenerational living is still relatively niche in London. In order to transgress from niche to norm, a combined effort from stakeholders and a different approach to how we develop our cities is necessary.