The group, with a Jaguar Land Rover worker at the helm, targeted luxury motors at addresses in Walsall, Cannock, Rugeley and Four Oaks, Sutton Coldfield, as well as Warwickshire and Derbyshire, during a campaign of crime that lasted from March 8 2015 and May 5 2017.
A sixth member of the gang received a suspended jail term.
Among the high-end vehicles taken were a BMW 6 series, an Audi A7, a VW Golf VRM and an Audi TT, Wolverhampton Crown Court heard.
The racket was uncovered by chance when a photography fan spotted four men acting suspiciously in Brueton Drive, Erdington, Birmingham, and took pictures of them which he handed to police.
GALLERY: Car key gang sentenced
The quality was so good officers were able to identify one of the cars as a £27,500 Mercedes stolen from an address in Clarion Way, Cannock, hours earlier during the night of April 16/17 2017.
The pictures captured the moment 26-year-old JLR employee Sikander Farooq, branded by Judge Michael Challinor as a "determined and callous professional criminal," got into the car after handing cash to Gavin Hladkiy, aged 36, who had brought the car to the rendezvous with 25-year-old "career burglar" Nathan Somers.
Alimaan Hussain, aged 27, whose family lived just yards away in Spring Lane, was also there.
The snap sparked a major crime investigation and one of the officers involved explained: "The man had his digital camera with him and took decent photos.
"It was a gut reaction prompted by something that looked dodgy to him as the men had arrived in different cars for a meeting in a side road in broad daylight. It is possible we might not have broken the gang without those pictures."
Professionally executed burglaries
The probe concentrated on its activity between March and May 2017 which ended with the photographed men in the dock alongside Alimaan and his brothers Adnan and Aqeel Hussain, aged 28 and 23, respectively.
Searches of the homes of the Hussain's and Farooq unearthed spare parts linked to vehicles that had been stolen in car key burglaries as long ago as March 2015.
A BMW found on the drive of one of the raided addresses had an inner wing from a BMW M3 stolen in Derbyshire in 2015.
Farook and Adnan Hussain were "at the heart" of the organisation, sending the burglars and dealing with the stolen cars, said Judge Challinor who continued: "The burglaries were planned and professionally executed.
"The number of them and the degree of planning illustrated the sophistication of the enterprise."
The court was told Aqeel Hussain, Hladkiy, Somers and two others, who have been dealt with separately, carried out the burglaries while Alimaan and Adnan Hussain together with Farooq received the vehicles and co-ordinated their disposal
Alimaan Hussain and Adnan Hussain both pleaded guilty to conspiracy to commit burglary. The latter was sentenced to three years and nine months while his brother, a talented boxer of previous good character, who admitted the offence on the grounds he was "drawn into" the conspiracy at a late stage, received a two-year suspended sentence with 200 hours unpaid work.
Farooq of Fellbrook Close, Stetchford, also of previous good character, was found guilty of conspiracy to commit burglary, conspiracy to handle stolen goods, and handling a stolen VW Golf VRM, after a trial and was jailed for five years.
Aqeel Hussain was locked up for two years and three months after pleading guilty to two counts of burglary and an attempted burglary.
Somers, of Tangmere Drive, Castle Vale, Birmingham, was jailed for three years after pleading guilty to burglary and handling stolen goods.
Gavin Hladkiy, of Wilmore Road, Perry Barr, admitted handling the stolen Mercedes and received a two-year three month sentence.
Det Sgt Jim Byrne from the Staffordshire Police Major Organised Crime Department said after the case: "This was a well organised operation where a group of men were targeting high end performance cars across the Midlands.
"Our detectives have worked hard and shown great tenacity to piece together the activities of these men since the investigation began in 2017."