Businessman Nick Grindley was woken in the early hours of Tuesday morning to hear his Uppingham shop had been raided for the second time in four months.
A neighbour had alerted police at about 1am after being woken by banging sounds. The neighbour shone a light onto three men outside the shop in Crown Passage and they ran away.
Mr Grindley arrived at work to find part of the door and wall of the Rutland Antiques Centre in Crown Passage demolished.
He said: "We've got new systems in place which kept them out of the shop, but they have caused thousands of pounds of damage.
"I feel disgusted that this keeps happening in Uppingham. These people don't want to work themselves and they just don't care about other people's businesses."
Antique jewellery was stolen in May when ramraiders used a car to force open the shop door.
The car thought to be involved this time was a silver Audi A3 which had been stolen from North Luffenham the night before. It has since been recovered from a ditch on the B1040 at Whittlesey in Cambridgeshire and is being examined by forensic teams.
This time nothing was taken but the shop will need major repair work.
Mr Grindley said: "The police need to do more about the crime happening in Uppingham. It is a small market town and incidents like this need to be taken seriously. These people seem to think they can get away with anything."
The shop opened for business again on Wednesday. Witnesses should contact Pc Adam Ploszczanski on 0116 222 2222 identification number 1681 or Crimestoppers on 0800 555 111.