Berlin police said Sunday that 123 officers were hurt in clashes with left-wing extremists who hurled rocks and bottles at them, smashed shop windows and set cars ablaze.
The overnight violence follows weeks of escalating tensions around a building that is a centre of the far-left youth scene. It has been repeatedly raided by police.
Police said Saturday night's protest was the city's "most aggressive and violent demonstration in the past five years".
Police had sent 1,800 officers to confront the 3,500-strong crowd. The officers used batons and tear gas as the situation deteriorated.
Eighty-six protesters were temporarily detained, with three facing a magistrate on charges of breach of the peace, police said.
The protests centred on a flashpoint building in the German capital's inner-east Friedrichshain district which regards itself as a militant bastion against rising rents and the gentrification of Berlin.
The city-state's minister in charge of security, Frank Henkel, denounced the "orgy of violence of the extreme left" by "anarchists and troublemakers".