A Java coffee house and a Shell petrol station were among business premises affected in an operation targetting illegal structures in Kileleshwa on Monday.
The business owners and employees were seen trying to salvage the little they could as a bulldozer brought down the structures.
The demolition was sanctioned by the National Environment Authority (NEMA). The agency said the building was put up on riparian land and is also on a road reserve.
Also pulled down in the 5am operation were several billboards and kiosks.
The authority says it gave the owners a three-month notice and extended it by a week but the same was ignored.
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Also, the highways authority KeNHA had earlier warned that structures built on Nairobi and other towns' road reserves will be brought down.
Governor Mike Sonko's administration had also warned that the demolitions will continue despite the resistance around the operation.
Sonko earlier said the affected would be relocated to better places, reiterating all illegal structures on road reserves will have to be brought down.
Nairobi Senator Johnson Sakaja and Embakasi East MP Babu Owino have opposed the 'inhumane evictions'.
So far, more than 2,000 structures have been demolished in Nairobi. Sakaja has called upon Sonko to be considerate.
He said the demolitions have left many residents hopeless as their only sources of livelihood have been pulled down.
Babu said: "You do not oppress the same people who elected you. This is wrong."
The exercise has seen business owners and traders, some who had taken loans, lose their property.