Large purpose-built retirement complexes including continuing care options are increasingly popular ways to ‘age in place’ for older people in New Zealand and internationally. Promoted by their corporate owners as a lifestyle choice offering a wealth of activities and social interaction in manicured settings along with security and increasing care on site as needed, these entities offer new ways for wealthier older people to age. Applying an ethnographic approach to a case study residential complex in Auckland, New Zealand, we explore how residents experience inclusion and exclusion, and sense of community within such environments with a diversity of fit and frail residents. Data was collected from interviews, walk-about conversations, social site mapping and a selection of media material to gain an understanding of the social issues important to the residents. The twelve participants, aged between 70 and 87, were all independent residents living in the independent part of the complex, which is situated in a socio-economically wealthy suburb of Auckland. We identified that social connections were often fragile, and existing social group membership was key to shared community experiences and a sense of belonging. Residents who found themselves on the social fringes, particularly as newcomers or through health decline, were at risk of marginalisation, stigma, and social exclusion. Further, we identified how the design and layout, and tensions in the structure of the resident-management relationship potentially hinder inclusiveness and sense of community. These findings shed light on alternative experiences at odds with the commercial and populist framing of these places as age-friendly and inclusive communities promoting active lifestyles.