The media mogul, 59, is offloading treasures from her homes in Hawaii, Indiana and California at a giant sale Saturday that will take up three tents on the polo grounds in Santa Barbara, Calif.
And for those who can't make it in person, there's an online sale, too, with all proceeds benefiting Lady O's Leadership Academy for Girls in South Africa.
"I've been accumulating things since 1985," Winfrey tells Entertainment Tonight. "It's just too much stuff. I talk about it a lot in [O] the magazine. We talk about decluttering. And I realized, I need to declutter my own life. It is very freeing. I am downsizing."
Autographed electric scooters? Check. A 19th-century doll, expected to go for up to $8,000? Check. A Louis XVI chest of drawers, perhaps the priciest item, worth up to $50,000? Check.
In fact, there are lots of dolls for sale. "People come to stay with me, and they say they get scared with all the dolls," Winfrey says. "You wake up, and there's like 12 dolls staring at you."
Not that it's easy for her to let go of some of this stuff. But for Winfrey, it's about practicing what she preaches.
"I'm trying not to be attached to things," she says. "I'm trying to live the life that I talk about, like not letting things define you. But it's hard."