During the last two decades, it has become increasingly popular to buy a second home, with a significant number of these acquired abroad. Several factors explain this trend, including: general growth in households’ income; more leisure time, longer holidays, part time employment; more flexible employment including remote working; the housing wealth effect; lower barriers of distance; greater mobility; the liberalisation of financial markets; domestic technology innovations; and new forms of hyper consumption (Paris, 2009). The demand for second homes by foreign buyers in Portugal has been increasing since 2013, in some cases surpassing pre-crisis demand. The motives of this new wave of foreign buyers in Portugal seem to have undergone significant changes. Before the crisis, the key motivations driving second home ownership by foreign buyers were leisure or lifestyle (holiday and or retirement) and investment (to let investment and resale potential and investment diversification) (King, Warnes and Williams, 2000; Janoschka and Haas, 2014). While increasing international investment in the Portuguese property market has attracted media and public attention, there are few studies that try to understand new buyer motivations. Similarly, there is a lack of both empirical and theoretical analyses that elucidate the way in which foreign second homeowners affect housing market dynamics. This paper aims to fill this gap through a comparative triangulated analysis of pre- and post- crisis motivations. We draw on a unique survey sample collected in 2006-7 of British overseas second homeowners. To understand the processes instigating post-crisis shifts, we draw on qualitative fieldwork conducted in 2016/2017 including semi-structured interviews with real estate professionals and other key actors. Alongside new motivations, our results reveal the continued importance of lifestyle mobility related with quality of life, lower costs of life, proximity, climate and security (Sardinha, 2013; Torkington, 2012, O´Reilly, 2007). Today, however, new incentives and strategies, related with taxation and immigration policy, are driving the increasing trend of second home buying in Portugal. We conclude that macro and micro factors related with changing economic and political factors provide the structural opportunities for a diversifying group of residential tourists, investors and migrants in Portugal and reflect critically on the sustainability of this trend.