In one case, the men poured milk onto a Stockport victim's driveway, claiming it was sealant, forcing him to pay £800.
Four family members have been jailed for cheating elderly and vulnerable people out of thousands of pounds.
Francis Tomney, 55, Francis Tomney, 22 and Thomas Tomney, 22, all of Cleveleys in Lancashire, carried out shoddy work on people's driveways - including using milk as a sealant.
Brian Tomney, 29, of Salford, conned an elderly woman with dementia into selling her £60,000 house for £17,000.
All four, who admitted fraud, were jailed at Preston Crown Court.
Francis Tomney senior was jailed for five-and-a-half years for conspiracy to commit fraud by misrepresentation and two charges of cheating the public revenue and handling stolen passports.
'Dishonest and fraudulent'
His twins sons were also given prison sentences. Francis Tomney junior was jailed for five years for conspiracy to commit fraud by misrepresentation and cheating the public revenue.
Francis Tomney, Brian Tomney, Francis Tomney, and Thomas Tomney The Tomney family's behaviour was described by police as despicable
Thomas Tomney was jailed for four years and six months for conspiracy to commit fraud by misrepresentation.
The trio were caught when they were filmed laughing about using milk to seal a driveway.
Brian Tomney was jailed for a total of five years for his involvement in a job undertaken by the Tomneys in Stockport, as well as the buying of the elderly woman's house.
He persuaded an 88-year-old woman with Alzheimer's, who he was doing building work for, to sell her home in Ashton Old Road, Manchester, in 2008 for £17,000. It was worth up to £70,000.
Judge Michael Byrne on sentencing said: "I am satisfied that on each occasion of these transactions they saw the customer as an opportunity to make money but the practices used to further this aim amounted to dishonest and fraudulent conduct in each case."
The Tomneys operated a business carrying out work on driveways at private addresses. The work was often shoddy and in some cases dangerous and victims were charged high prices for work that was either poor or incomplete, police said.
Work was carried out in Knott End, Preesall, Fleetwood, Blackpool, Thornton, Lytham, Stockport and even as far afield as St Albans.
Almost £500,000 in cash and a video demonstrating the fraudulent scheme were discovered by police during an investigation of the Tomneys for other criminality.
Det Insp Gary Brooks, from Lancashire Police, described the family as "organised criminals" and said their behaviour was "despicable".
He said: "We discovered a video demonstrating they were also involved in fraudulent activities where they were targeting old people and conning them out of money.
"Essentially the Tomney family have charged [a man] £800 for sealing his drive; in actual fact it is a bottle of milk. You can see them pour a pint of milk into a container suggesting that is the chemical they're going to treat his driveway.
A drive in Stockport which the Tomneys had worked on Brian Smith's drive in Stockport was originally costed at £400 but this then doubled to £800
"It shows them laughing and joking which just shows the callous nature of these criminals."
Det Insp Brooks said the Tomneys would use "aggressive and intimidating tactics" to get more money from their victims.
"They would be instructed at a reasonable price and they would pretend then to find other work that needed attention and escalate the price.
"The price would be known to double or even quadruple."
One of their victims, Brian Smith, from Stockport, said he was originally quoted £400 but this was doubled to £800. Then they poured white liquid on the drive.
Mr Smith said: "My wife was getting very apprehensive about it. She didn't like them and said 'pay them and get shut of them'.
"I've since learnt the white liquid was milk and I felt foolish but I felt very apprehensive."
Trading Standards said it had identified 51 victims of the Tomneys but believed there were many more.
John Dilworth, from Crown Prosecution Service, said: "These defendants deliberately targeted people who they thought it would be easier to defraud.
"They were superficially charming with victims but in reality treated them with contempt and, in some cases, conned retired people out of their life savings."
Det Insp Brooks said efforts were being made to use cash seized "gained from criminal benefit" to compensate the victims.
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