The problem of homelessness has increased to a great degree in the last decades. In Estonia, homelessness became an urgent issue in the mid-1990, but until now has not been studied much. The aim of this paper is to describe the homelessness situation in Estonia in both the historical and the present-day perspective. The article is based on an empirical study conducted in the city of Tartu. According to social work experts, the number of homeless people in Estonia has grown in the last several years, reaching 3,500. In Tartu alone, there are approximately 200–300 homeless people.The study was conducted using the quantitative method. The sample group consisted of 57 homeless people. A questionnaire was used for the collection of data and the questioning was performed in the form of face-to-face interviews. In this paper authors give an overview of the reasons for loss of a home, the relationship of the homeless to their families, their health condition and aspects related to their working lives.