The acquisition of a plot of land is a complex legal transaction. When a foreign element is added to this transaction, the complexity inevitably increases. In the interest of promoting the proper functioning of the EU internal market, this study investigates how this complexity can be reduced. To this end, it offers an in-depth study of the land registration systems of the Netherlands, Germany, and England & Wales to understand how differentland registration systems unfold in legal practice. It then provides an overview of the various challenges that are faced by the different stakeholders that are involved in these transactions. Subsequently, the already existing initiatives, that aim to contribute to a facilitation of cross-border real estate transactions, are discussed. After having synchronized the identified challenges with the solutions provided by these initiatives, different strategies to further reduce the remaining challenges are evaluated. Given that the study is enriched with insights from the reality of legal practice, it is of interest to academics and (legal) practitioners in the field.