In real estate development, fund-raising methods through project financing have been established as a common approach. In the old practice of real estate project financing, contractors offered credits such as joint surety, takeover of debt, completion guarantee, and sales guarantee for the debt of the project company for financial institutions. When a contractor offers credits for the implementation of a project, the project can be propelled in a stable and fast manner. However, many projects were carried out through the credit enhancement of contractors, it worked to deteriorate the financial soundness of the contractors. It even had negative impacts on financial institutions that had nothing to do with the projects via the contractors. Those problems have recently led to attempts at structuralization through new and diverse methods of credit enhancement including condition takeover of debt, secured loan commitment for unsold estate, and advance subscription and rent instead of the old credit enhancement method that imposed all the project risks onto contractors. However, there are no specific discussions about the legal effects of those new methods of credit enhancement. In addition, there are many cases in which a contract is concluded with the concerned parties having no clear perception of legal effects. Contractors are still burdened with ultimate risks with the possibilities of expediency and illegitimacy. Real estate development through project financing seems to continue its expansion, but the current practice of real estate project financing is nothing but an altered version of the old financing approach. The limitations of real estate project financing dependent on contractors should be overcome by searching for an investment structure proper for projects through structured financing and new institutions.