Inside Oprah Winfrey’s Tortured Childhood Homes—and Rise to Real Estate Stardom—as She Opens Up About Traumatic Rift With Her Mom

Oprah Winfrey is one of the richest women in Hollywood, having built up an extraordinary fortune that includes a TV network, a production company—and a collection of truly exceptional homes.

But the 71-year-old billionaire has now candidly revealed that all of that fame and fortune have long been tainted by a very painful childhood trauma she still struggles to deal with many decades later: her relationship with her mother, Vernita Lee, who died in 2018.

Lee was 17 when she gave birth to Winfrey in 1954. Lee was still living in her childhood home in Mississippi, and the TV mogul spent the first years of her life being raised by her grandmother in that house.

Today, the house in which Winfrey was born has been razed and its location has been turned into a tourist attraction.

“On January 29, 1954, Oprah Winfrey was born in a wood frame house located on this site,” states the plaque.

Now, in a new episode of “The Oprah Podcast,” Winfrey has tearfully revealed that the pain of her childhood has only built up over time and that she still grapples with the fraught relationship with her mother to this day.

She confessed that she has always struggled to think of anything positive to say about her mother, recalling a time when she was asked to speak about Lee at their church.

The only thing she was “grateful” for where her mom is concerned is that she didn’t “abort” her when she learned she was pregnant, Winfrey said.

“I had been asked to come to church to give all these accolades about my mother,” she said. “It was important for her to be seen as religious in the community, and I couldn’t think of one thing.

“I was like, ‘Oh, my God, I don’t have one memory.’ And so, when it came time for me to speak, I thought, ‘Well, what do I actually have to be grateful for?’ She didn’t abort me. She did the best that she knew.”

Winfrey went on to explain that her mother was not capable of giving her what she “needed” throughout her life, conceding that Lee did “the best that she could do,” even though that was not enough.

“The best that she knew was not enough to feed what I needed, was not enough to make me feel whole, was not enough to make me feel valued or seen or important to her. It was not,” Winfrey said.

“But it was the best that she could do, and I gave up the hope that it could have been anything other than what she had.”

Winfrey previously confessed that she found it difficult to comfort her mom when she was nearing the end of her life in 2018.

“In hospice care, they have a little book about the little conversations,” Winfrey told People magazine shortly after her mother’s death. “I thought, ‘Isn’t this strange? I am Oprah Winfrey, and I’m reading a hospice care book on what to say at the end.’

“She’s sitting in this little room—she loves sitting in this room where it’s 80 degrees. She just watches TV all day.

“What I said was, ‘Thank you. Thank you, because I know it’s been hard for you. It was hard for you as a young girl having a baby, in Mississippi.

“‘No education. No training. No skills. Seventeen, you get pregnant with this baby. Lots of people would have told you to give that baby away.

“‘Lots of people would’ve told you to abort that baby. You didn’t do that. I know that was hard. I want you to know that no matter what, I know that you always did the best you knew how to do. And look how it turned out.'”

When Winfrey was born, her mother was working as a housemaid, while living in a small home on a farm in Kosciusko, MS.

The land where the property once sat is located off of Oprah Winfrey Road, which runs north of Highway 12 and is near the church where she first spoke as a child. It was renamed in honor of the TV mogul when she first rose to success with her popular daytime show.

Winfrey lived in the home with her grandmother Hattie Mae (Presley) Lee until she was 6, at which point she moved to Milwaukee to reunite with her mother, who had run off to work as a housekeeper in Wisconsin after giving birth.

Winfrey moved into a multifamily property with her mother and lived there for three years until relocating to Nashville.

When Winfrey was 9, Lee sent her to live in Nashville with her father, Vernon, and his then-wife, Zelma, who became something of a surrogate mother for the young TV star.

While in Tennessee, she attended East Nashville High School, won the Miss Black Tennessee beauty pageant at age 17, and won a scholarship to Tennessee State University.

She also worked as a part-time news anchor at WVOL radio station before becoming the first African American female news anchor at WLAC-TV in 1974.

By 2000, Winfrey’s father had separated from Zelma and was set to tie the knot with his then-partner, Barbara.

To help the newlyweds celebrate, Winfrey bought them a stunning four-bedroom, five-bathroom property in 2000. Though she had purchased it as a wedding gift, Winfrey’s name remained on the deed while her father and his wife lived there.

The property became a point of contention in 2014 when Barbara and Vernon were divorcing.

Following their divorce, the TV mogul reportedly put the home on the market for $1.5 million and kicked her former stepmom out.

At the time, Barbara told the Daily Mail that she “lost everything” because of Winfrey.

The home was sold for $1.2 million and hit the market once again for $1.5 million in 2017. It was sold within a month for $1.49 million.

Although she is no longer the owner of the Nashville home, Winfrey boasts an incredible collection of homes from California to Hawaii. In total, her real estate holdings are estimated to be worth around $158 million.

Her main stateside residence is in the coastal enclave of Montecito, CA, where her neighbors include Prince Harry and Meghan Markle, Gwyneth Paltrow, and Ellen DeGeneres and Portia de Rossi.