This paper aims to introduce new evidence of consistently negative impacts on enterprise value when corporations increase real estate holdings. Adopting a different approach from previous studies, our data analysis shows that corporate real estate portfolios and enterprise value share an inverse relationship. Surprisingly, this trend was seen during the Japanese real estate bubble in the late 1980’s. Previous reports from the United States and Singapore show that only in the retail sector do increases in corporate real estate holdings have a positive influence on stock performance. However, our research indicates that the stock performance of Japanese firms in the retail sector was negative across the board for firms in other sectors.