This paper tests for speculative bubbles in the medieval English property market based on a unique hand-collected dataset from the feet of fines spanning the fourteenth and fifteenth centuries. We focus on asset types where there are sufficiently large numbers of transactions each year to make a long and reliable run of information, and we transform this into annual time-series of prices. We employ a regime switching model that allows for boom and crash episodes to characterise and test for bubble dynamics. The results are consistent with the presence of periodic, partially collapsing speculative bubbles in the market for agricultural land, but there is no such evidence in the context of messuages. Our findings demonstrate that the medieval English property market shares important features with its contemporary counterpart, for instance with the recent so-called ‘barn bubble’.