Birmingham-based Gurtake Singh preyed on the goodwill of people with sob stories claiming he needed taxi money to visit ill relatives in hospital, West Midland Police told Birmingham Crown Court.
He deceived people into giving donations of 20 pounds to 350 pounds. Singh, who referred to himself as "Mr Con", admitted 11 counts of fraud and one of theft.
Detective Sergeant Phil Poole of West Midlands Police said: "Singh's tactic tended to be knocking doors in a panicked state, sometimes crying, in order to gain entry.
"Victims described him as friendly and charming, even kissing them on the cheek and accepting drinks while engaging them in conversation. He was very plausible and showed no remorse for the people he conned."
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Singh first struck last June when he was allowed into the home of a 69-year-old man where he convinced the victim to hand over 30 pounds and swiped a silver cup on leaving, 'Birmingham Mail' reported.
He also scammed 150 pounds from an 82-year-old woman and returned the next day with fruit to say "thank-you" - before getting her to take out another 350 pounds to help pay for a medical trip to India.
Poole added: "He knew the names of the residents he approached and also names of neighbours.
"It was all calculated to offer them reassurance, that he was genuine, and would honour claims he'd return the money."
Singh was jailed on Monday for three years and one month and also ordered to pay back 1,552 pounds compensation to his victims and banned from cold-calling addresses or asking people in the street for money.