During the transformation period after 1989, Czech cities (similarly as other cities in the former eastern bloc) went through a dynamic development in many areas. Our contribution deals with one of the key areas of postsocialist transformation of the city, specifially the humanization of mass housing in large housing estates. These housing estates creates heritage from central planning period, which in many Czech towns cannot be overlooked. At the beginning of 1990s, housing estates suffred from a number of drawbacks that needed to be put right. The paper describes more than two decade-long process of housing estates humanization which gradually led up to the removal of monofunctional (strictly residential) model and settng the multifunctional model. This leads to improvement of civic amenities, implementation of new urban-architectural solutions and creating new job opportunities. As a result, these changes increase the quality of life in housing estates, both in terms of objective and subjective point of view.