Tony Keating, who lives in East Pallant, was abruptly woken up when a van collided with his 16th century house.
“I thought it was an earthquake or an explosion,” he said.
He is now calling for steps to be taken to stop it happening again.
Tony said: “So much effort has been put into conservation in Chichester and particularly the Pallant so it seems a pity that one of the oldest properties can be subject to regular damage from lorries and cars.
“Particularly when a couple of bollards could so easily protect the building as in so many other parts of the city.
“We are meant to be conservation minded so we should protect our buildings surely.”
West Sussex County Council said it is looking into the issue.
A West Sussex County Council spokesperson said: “We were sorry to hear the building has been damaged.
“Officers have met with Pallants Residents’ Association a number of times in recent years and discussed ‘historic building strikes’ at this location.
“Ultimately it is down to road users to exercise appropriate care on the road network.
“However, in more recent years we have improved signage and reprofiled the road to try to improve the situation for the affected residents.
“The residents’ association contacted us about this latest incident and we will investigate and respond to them directly.”
Chichester District Councillor Anne Scicluna said: “It’s tragic because it is a beautiful building. They are all listed and in a conservation area.
“It’s a lovely part of Chichester and we have got to protect it. It’s a matter of getting everybody together and sorting this out.”