The latest trend in homelessness in Australia relates to older women who have become unexpectedly homeless or who are currently at housing risk for the first time, later in life (Westmore & Mallett, 2011). Identified in the literature as the silent and hidden women (McFerran, 2010) little is known about the experiences of these women who do not seek help until their situation becomes critical. This research enquiry seeks answers to the question “What are the lived experience of older women who find themselves unexpectedly homeless, or at housing risk for the first time later in life?”. Using a feminist, participatory, heuristic framework, I invited older women to participate in individual interviews to discuss their lived experience of homelessness. Prior to the interviews taking place, I volunteered as a Community Cultural Development worker/artist within a women’s shelter, a social housing complex and community-based drop- in centre to better understand the context surrounding homelessness for vulnerable women. Within this role, artmaking was used to start conversations with the women and to develop the research question. Drawing upon interviews with twenty women aged from forty-five to seventy-seven (average age of fifty-seven years and seven months), and through a continued creative process, new insights into the experiences of older women who found themselves unexpectedly homeless or at housing risk, emerged. Four key themes were identified - family of origin, living with uncertainty, the journey from hopelessness to hope, and the journey of belonging. Further findings reflected a number of important ‘tipping points’ experienced by older women who were homeless or at housing risk, and revealed an interconnected set of factors that contributed to lived homelessness. Overall, this research uncovered an understanding of how these older women navigated their journey from a feeling of hopelessness to a feeling of hope about their future. This research is a testament to hope, belonging, and ‘the space in-between’, the transitional space, as described by Winnicott (2002). The findings confirm that using an art-based, feminist participatory, heuristic methodological approach was a useful way to connect with this vulnerable population of older women. The findings also provide guidance for policy makers and service providers about the needs of this currently increasing cohort of older women who become unexpectedly homeless or at housing risk for the first time later in life.