Jumbo was a Sulphur Point regular, dossing down on what he could find, rain or shine.
He now rarely ventured into the city, he said.
With the help of LifeLink Samaritans manager Kay Brown and Rotorua Rentals, the 47-year-old is feathering a new nest in a modest two-bedroom flat, with a bathroom, kitchen and television. He was rapt when told he had a flat, he said.
"I didn't think it would ever happen. I counted the days, week after week, year after year I had been on the street, and I had almost given up."
On the first two nights he slept on the floor, out of habit, before he found his comfort zone, he said.
"Sleeping in a bed was like sleeping on cloud 12, bro," he said. "I just wanted to get off the street, it wasn't cold in winter but I wanted to have a roof over my head."
It is no luxurious lifestyle. The $145 weekly rent is paid automatically from his benefit, leaving $118 for food and power.
The quiet location, with trees and sun, was "perfect", said Ms Brown. "We had to find a place suitable, I couldn't be happier for him."
Getting Jumbo into the flat is only the tip of the iceberg, she said.
"Keeping him there over the winter will be the real test."
Jumbo, a former Wellington City Council gardener, wants to lead a better life.
"I'm not one to be sitting around," he said. "I had it sweet, I had no one to answer to but the reality was I had to start again somewhere. It can only start if you want it, you are the only one who can make it happen.
"I don't want to go back."
He began to change his life after Maori Warden Raelene Tokona suggested he join the wardens, he said.
Buoyed by new living conditions he signed up in April as a volunteer three to four hours a day at the Brooklands shopping centre.
"He's come a long way since he was on the street, he's doing really well," said Raelene.
Homeless advocate Roger Brown said Jumbo had shown initiative.
"He has shown others what is possible."