The UK experienced a substantial rise in owner occupation over the twentieth century. Despite the recent fall in ownership rate, many tenants still aspire to own their own homes. These strong aspirations to own are attributed to a set of financial and non-financial benefits. Although the financial benefits are perceived to be significant and to outweigh housing benefits, there is a paucity of rigorous research measuring and confirming the significance and nature of the financial benefits from buying versus renting. This research calculates, for the first time, the historical pure financial returns from buying versus renting in Britain for first-time buyers and disaggregates the results by the eleven regions. It investigates whether the long-term growing homeownership aspiration in Britain has been sustained and rationalised by solid financial payoff or not. It is based on a DCF analysis of historical housing and mortgage market data from 1975 to 2012. The empirical analysis produces more than 18,000 simulations using a comprehensive financial model. The results of the research explore the return from house purchase differential between regions and develop a regional return ranking. It also explores the historical contribution of capital gains to the overall return by calculating the returns after excluding capital gains. The research investigates how much timing matters by comparing the returns at (or near) peaks and troughs over the major three housing cycles. The research finally explores how many holding years were historically required in order for house purchase by first time buyers to breakeven.