This article re-examines the late medieval market in freehold land, the extent to which it was governed by market forces as opposed to political or social constraints, and how this contributed to the commercialisation of the late medieval English economy. We employ a valuable new resource for study of this topic in the form of an extensive dataset on late medieval English freehold property transactions. Through analysis of this data, we examine how the level of market activity (the number of sales) and the nature of the properties (the relative proportions of different types of asset) varied across regions and over time. In particular, we consider the impact of exogenous factors and the effects of growing commercialisation. We argue that peaks of activity following periods of crisis (Great Famine and Black Death) indicate that property ownership became open to market speculation. In so doing, we present an important new perspective on the long-term evolution of the medieval English property market.