Manuscript Type Empirical Research Question/Issue This paper examines real estate transactions among Korean listed firms, their affiliated companies and controlling shareholders from 1999 to 2011. The goal of this study is to test whether the controlling individuals gain higher returns from the trades than the other parties in a persistent manner. Research Findings/Insights Investigating price changes across the transactions reveals that the controlling shareholders consistently earn higher returns than the listed firms, while this is not the case for the affiliated firms. The listed firms, in expectation of bleak potential in value growth, acquire real estate properties from their controlling shareholders while disposing of properties with promising prospect of growth in value. When the listed firms either buy or lease a property from controlling shareholders, the market value of the acquired property increases less than the leased. Theoretical/Academic Implications All of the findings confirm a tunneling nature of the listed firms’ real estate transactions with their controlling shareholders. Practitioner/Policy Implications The findings show a possibility that listed firms and the controlling shareholders can plot property transactions so as to offer biased profits for the individuals at the expense of minority shareholders. Such profitability becomes viable by manipulating transaction timing and does not necessitate predatory pricing of the assets transferred.