He sets off to work each morning, strolling with his dogs across the vast grounds of his 16th century country estate west of London, looking precisely like the country squire he has become.
This is a fantasy that's become real.
When he was 19, Winwood wrote the classic, "Dear Mr. Fantasy." It was an ode to the potential pitfalls of celebrity. Nearly 40 years later, he seems to have avoided all of them. He shied away from the sex, drugs and rock 'n roll lifestyle we usually associate with rock stars.
"There are lots of people that live that lifestyle that I've known who aren't alive anymore," he said. "So perhaps there's an element of survival in it."
Unlike so many of his contemporaries, Winwood hasn't merely survived, he's thrived. And he's made his share of history along the way.
Looking back, it seems he was born into a musical life. It was 1948 in Birmingham, England.
"My father was a musician, a semi-professional musician," he said "I used to go and play with him when he did gigs, played at weddings or that kind of thing. And I'd be one of the band."
One of the band at age 9. The word 'prodigy' might have been invented for him.
"When I was 14, it was probably a bit worrying for my parents. I had no interest in anything, even gave up sports. I mean, I used to play a lot of sports. Stopped all that when I was about 13."
He blames it on his obsession of music. But the obsession soon started to pay dividends. He quit school at 14. At 15, he joined The Spencer Davis Group, which took off. And by 16, he'd written his first big hit, "I'm a man."
"I never thought of myself, leading up to that time, as a singer, probably because when I first started playing, my voice hadn't broken. You're never sure how your voice is going to turn out."
His voice turned out fine. A student of American blues and soul music, Winwood was just 17 when he wrote the song that guaranteed his place in rock history, "Gimme Some Lovin'."
It was an instant classic. I was also young Winwood's first encounter with what would be a lifelong tension between commercial and artistic success.
"Obviously, there were other people that were quite happy that it was a worldwide hit. But for me, personally, that wasn't the major goal."
What was the major goal?
"The major goal was to create this music out of rock, blues, and bits of ethnic music and English rock … It was an accidental hit."
Winwood's career became a multi-hit pile-up of happy musical accidents.
His next band, Traffic, is still regarded as one of the most innovative rock ensembles of all time.
And with fame, came money. And it was not to be blown in that rock 'n' roll kind of way, but to be invested in his country estate.
He was 21 when we bought it. But, this being rock 'n' roll, he bought the place not for the peace and quiet, but rather for the noise he and his new band could make.
The new band was "Blind Faith," the first so-called super group, which united Winwood with another up and coming British rock heavyweight, Eric Clapton.
Winwood was on the fast track. But after just one hit album, Blind Faith collapsed under the weight of its own expectations.
Winwood's music became more introspective, and thus less radio-friendly, through the '70s and early '80s. Then just when his superstar status seemed have permanently faded, he stormed back with "Back in the High Life." The 1986 album became his biggest hit ever, earning a Grammy award for record of the year.
A year later "Roll with It" was bigger still. Winwood had become the thing the music industry loves best, a hit machine. He was even one of the first to turn a hit song into a hit commercial.
He was rich, but was he happy in his work? "All through the kind of late '80s and '90s, every A&R record company man was saying, now what we want is another record like 'Back in the High Life.' And, of course, that's not the way to make music at all. That's the tail wagging the dog."
So Winwood walked away from the high life, and rediscovered the joys of country life —and the joys of married life.
Around that time he met and married his wife of 19 years, Eugenia, with whom he's raised four children.
Is it difficult to have a normal family life and be the wife of a rock 'n' roll musician at the same time?
"Steve is a great father," said Eugenia. "He really enjoys spending time with the children. I think the most difficult part about it is the touring."
So now, when he does tour, Winwood simply brings some of the family with him. Daughter Lilly is already showing signs of taking over the family business with her guitar playing.
But mostly his life centers around the homestead, keeping up with the demands of a 500-year-old estate, and "commuting" to the studio in his barn, where he still fires up the old Hammond B-3 organ that has been his signature sound from the beginning.
It's also where he's working on a new album, his 24th. His music — the kind he wants to do — still sells. And he's just released "The Last Great Traffic Jam," a documentary of Traffic's 1994 final tour.
Two of Winwood's mates from that band, Jim Capaldi and Chris Wood, are gone. But Winwood remains true to their memory — and to himself — by doing what he's always done: following his obsession with music.
"I suppose the thing that very first started to drive me when I was 13 or 12 or 9 (was) a love of music, and I enjoy playing it," he said. "I'm discovering more about music all the time."
It almost sounds like he couldn't stop if he wanted to.
"I don't think so."