This paper is a theoretical examination of untaxed and taxed entities that invest in real estate. The standard advice to real estate investors is to avoid using entities that are subject to taxation (such as C corporations in the U.S.) and employ entities that are not subject to taxation (such as limited liability companies, S corporations, and real estate investment trusts in the U.S.) in order to avoid double taxation of income. This paper shows that, in most situations, untaxed entities place a greater value of a given real estate property than does a taxed entity, which implies that taxed entities are at a distinct disadvantage at competing in the market for property. However, this conclusion is reversed if untaxed entities use a large amount of financial leverage compared to taxed entities and the borrowing rate for both is greater than the risk-free rate.