This explorative case study focuses on property investment decision-making from a behavioural perspective on the very micro level. The study aims at contributing to the understanding of how property investors manage the decision-making process, including issues like organising, valuing and financing. By applying a qualitative approach, we analyse an extraordinary large transaction that took place in the Swedish property market 2008. In an open bid transaction properties of the corporation Vasakronan was sold for SEK 41.1 billion (equal to € 4.3 billion). Managers in both the purchasing company and the consortium with the second highest bid were interviewed. They were encouraged to speak freely, but we also supplied an interview guide with a number of themes as well as specific questions. The findings reveal two types of characters in property investment decision-making behaviour with respect to how actors can organise the work and use external consultants, value the properties, and secure the financing necessary for a final bid. We use a qualitative empirical approach to analyse an extraordinary large property transaction from a buyer’s point of view, and we present detailed information about this transaction as well as general insights about actual behaviour rarely revealed in previous research or textbooks.