The housing histories of many Australian boomers will influence their housing choices as they move into the second decade of the 20 Century. Most Retirement Village providers acknowledge that new housing models are required to cater for the aspirations, needs and requirements of the boomer generation as they get older. In addition, climate change and concerns around sustainable living patterns are gaining prominence. The key to future boomer housing is the provision of sustainable and affordable housing landscapes that promote the health and wellbeing of residents for the duration of their life. This paper focuses on Gold Coast housing landscapes, a current hot spot for retirement living, where a number of innovative boomer housing projects are currently being developed. Research will map past and current boomer housing trajectories and ask what of tomorrow's housing landscapes and what can be learned from past housing practices? And in particular with regard to the health and wellbeing of residents, housing affordability and sustainability. To this end a comparative analysis is undertaken between existing 1980s suburban development (the 'Then' of our story) and more recent development in the mid 2000s (the 'Now' of our story). The aim of this analysis is to identify factors that foster healthy ageing of residents and position these at the centre of calls for sustainable and affordable boomer housing landscapes for tomorrow. This research is significant because it contributes to the growing body of knowledge around housing for an ageing population. There is an urgent need for policies to reflect and support these emerging housing landscapes and this paper will go some way to inform decision making processes.