David Anthony Cave, 47; Colin Andrew Redshaw, 29; and Paul James Donnelly, 35, travelled to the North Yorkshire market town on October 24, 2020, in a stolen black Ford Fiesta ST which was displaying false number plates in a bid to evade detection by police.
When they got to Helmsley, the men entered the garage of a house on Orchard Way, where they stole the three high-valued mountain bikes.
Police were alerted to the burglary and a tactical operation was launched to intercept the car and arrest the trio.
Within 30 minutes, the black Fiesta was sighted by officers on the A170 at Helmsley heading towards Sutton Bank.
A stinger device was deployed to burst its tyres and it came to a stop at the top of Sutton Bank, having left the road and coming to rest on the bank side.
The men were swiftly arrested, the stolen car was secured, and the three mountain bikes were recovered from inside the vehicle.
All three men were charged and remanded into custody to appear at court.
Pleading guilty to burglary, they were sentenced at York Crown Court on Tuesday.
Redshaw, of Brough Court, Middlesbrough received a three year sentence, while Donnelly, of Bolton Court, Middlesbrough was jailed for two years and eight months.
Detective Constable David Adams, who led the North Yorkshire Police investigation, said: "The three men involved in this incident have rightly been given considerable custodial sentences.
“They now have time to reflect on their despicable actions and are facing the consequences for this brazen act of burglary of high-value property in broad daylight.
“It was motivated by greed to line their own pockets at the victim’s expense.”
“The North Yorkshire Police officers who were involved worked quickly and effectively to make sure the stolen vehicle and its occupants were safely stopped, and that the stolen mountain bikes were recovered and later returned to their rightful owner.
“I thank the victim in this case for their support and co-operation with the police investigation. I hope this result brings them some closure on an ordeal which no one should have to experience.
“Burglary is an awful crime and very often has a significant impact and long-lasting effect upon the victims.
“This case also sends out a very clear warning to cross-border criminals who intend to travel into North Yorkshire – you will be caught and held to account for your actions.”