Important residential buildings and estates from the early 20th century are recognized as housing heritage. Five (former) workers’ housing estates in Austria (Eysnfeld, Steyr; Knappensiedlung, Hüttenberg) and Germany (Fritz-Schumacher-Siedlung, Hamburg; Ernst-Thälmann-Park Siedlung, Berlin; Piesteritz in Lutherstadt Wittenberg) together illustrate a complex field of conservation, adaptation, and participation regarding the management of change. The article argues for a sincere need for negotiation between different actors such as residents, owners, heritage authorities, and urban development authorities. Within this complex constellation of actors, we must weigh up heritage values and conservation practices, possible and necessary changes, as well as private, com-munal, and public interests. Thus, conservation and adaptation require broad participation if heritage protection is to exist not only on paper but in practice.