Gavin Hunt, 41, from Tile Cross, and brothers Christopher Dixon and Jamie Dixon, both from Castle Bromwich, used axes and crowbars to break into homes.
They then demanded car keys and cash.
Hunt was jailed for 12 years and 10 months, Jamie Dixon, 32, to eight years and 10 months, and Christopher Dixon, 29, to seven years and three months.
The three men, who wore balaclavas, targeted homes with expensive cars parked outside.
In one case in January 2013, Hunt and Christopher Dixon smashed into a house in Newton Road in Great Barr, where they pulled a nine-year-old boy from where he was hiding behind the sofa and threatened him with an axe while his family found the car keys.
The men stole a Nissan Pulsar GTR in the Great Barr robbery; an Audi R8 from Grange Park, Northampton; an Audi RS4 from Tile Cross Road in Birmingham, an Audi RS6 from Western Road in Sutton Coldfield; and an Audi RS4 from Oldburgh Drive in Loxley, Warwickshire.
Det Con Damian Forrest, from West Midlands Police, said: "I have no doubt that the gang would have used serious violence to achieve their objectives if they had not got what they wanted."
Correction 23 September 2014: In the original version of this story it was not made clear which defendants were involved in the offence in January 2013. The story was amended following clarification by the Crown Prosecution Service.
Three men have been jailed for a series of robberies across the Midlands, including one in which a nine-year-old boy had an axe held to his throat.