Moscow city authorities unleashed 700 bulldozers overnight to tear down 97 buildings recently deemed illegal by the mayor's administration, state media reported Tuesday.
Photos of the buildings widely posted on social media showed shocked workers milling about as their businesses were razed.
Many of the buildings, primarily made of sheet metal and plastic, hosted convenience stores and eateries and were built with dubious permits after the Soviet Union collapsed two decades ago.
"The majority of these unlawful structures were directly above underground utilities infrastructure - telephone lines, gas pipes, heating systems, power grids, etc," the head of the city's building inspectorate, Sergei Shogurov, said in comments carried by state news channel Vesti.
Local authorities began tearing down smaller kiosks of similar design as part of a citywide beautification project shortly after Sergei Sobyanin, a former head of the presidential administration, was appointed mayor in 2010.
Sobyanin said Tuesday that the buildings destroyed the previous night were "dangerous for Muscovites" because they were located too close to metro stations or on utilities infrastructure.
"Most of the structures were built in the 1990s with clear condonation or assistance by officials," Sobyanin said in a post on the Russian social network VKontakte.
Lawyers protested that such buildings had permits and were razed without court approval.
"What Sergei Sobyanin did can be described with only one word: banditry," lawyer Artur Airapetov told radio station Kommersant FM, adding that last night Moscow returned to the near anarchy of the post-Soviet 1990s.
"In 2015, Mr Sobyanin lost absolutely all of the court cases on removing such real estate. When he lost these cases - and I want to note that he lost not only in courts of primary jurisdiction, but all the way up to the Supreme Court - he issued an illegal decree," Airapetov said.
In December, the city's administration decreed that over 100 such buildings had to be removed within 90 days, according to a copy of the order on the government's legal information website.
"What happened is largely reminiscent of a special operation," popular blogger Ilya Varlamov said in a LiveJournal post with dozens of photos.
"Yesterday morning they began cutting the buildings off from utilities, then toward the evening everything was cordoned off by the police," Varlamov said. "At midnight, bulldozers all around Moscow started demolition. Today we've woken up to a different Moscow."
Alex Shifrin, a Canadian who ran a chain of soup kiosks in Moscow before his outdoor business model for "SoupChik" was ruined amid such demolitions in 2010, expressed empathy for the business owners, as Russia is struggling with an economic recession.
"At one point we had six locations. Two of them were taken down: one with a bulldozer, and one they just turned off all the power and told us to pack up and leave, which we did within two days," Shifrin told dpa.
"I feel for the business owners - those are real families and real jobs," Shifrin said. "Thriving entrepreneurship and the rule of law is no match for runaway corruption and common disregard from the regulators."