The incident which caused damage to Newby Road Farm, just off Scalby Road, is being investigated by police.
A lamppost, a tree and the street sign were demolished by a Mercedez Benz lorry this morning, around 6.15am.
Since the road closed on Monday, cars and lorries have often been spotted using the residential street to reverse and drive back.
Residents say motorists are driving all the way to the junction because of confusing road closed signs.
Officers are appealing for anyone who was in the area at the time and witnessed the incident or has any dash cam footage.
Anyone with any information should call North Yorkshire Police on 101 press option 2, and ask for PC 698 ADAMS quoting incident number NYP-20022019-0069.