The Inside Story of Oprah Winfrey's Multi-Billion-Dollar Fortune: Yachts, Horse Farms and So Many Mansions

Oprah Winfrey really rich. No really, we mean madly rich.

This is old news, in fact. But have you ever sat down and thought about how she lives? Thought about how much money she is worth? To start, she is currently worth $2.9 billion. According to Forbes, Oprah Winfrey  is the second richest woman in America, counting only those who have self-made fortunes. She is the owner of a television company OWN, of course, and also Weight Watchers, which brought in over $1 billion last year. 

She is America's first black woman to become a billionaire, a fact that is equal parts frustrating and impressive in its tardiness. She has enough money to finance OWN entirely out of her own pocket for the next two decades. She is worth more than several small countries. If you laid out her fortune in cash it is going to weigh 60,000 pounds. It is almost impossible to be jealous, because her life is just too great to fathom. 

The media giant spends a lot of her time working hard at taking over the world, but she also manages in plenty of opportunities to spend that hard-earned money. One of her lucrative hobbies is real estate. Winfrey owns a lot of wonderful homes. 

First is a 23,000-square-foot home in Montecito, a tony enclave outside of already-tony Santa Barbara,  that she bought for $50 million in 2004. (Let us all take a moment to imagine how much $50 million was 14 years ago.) The house was so beautiful that she actually ended up shelling out to hire a team of architects and designers to give it a make under. 

Then her other Montecito compound—because why own one hillside southern California mansion when you can actually own two? She acquired this property some years ago, and it is decidedly more fabulous than the first. But before you picture a quaint little cabin in the woods, know that it is actually a 23-acre horse farm that cost $28 million. 

For her vacation purposes, Winfrey usually go to Maui, where she has a 163-acre property with a very beautiful renovated farmhouse on the property, or  to Jackson Hole, where she has a $14 million home complete with a treetop fire pit, whatever that means. 

But what good is a bevy of beautiful mansions at your disposal if you cannot escape them to an even nicer locale? Enter Oprah Winfrey's enviable vacations. 

There is no way that a person can put on the daily grind that the media giant does without occasionally pressing pause to recharge, and that is exactly what she does, to a fascinating degree. Most of her vacations are done in tandem with her BFF and permanent travel partner, Gayle King (Oprah’s partner Stedman Graham keeps a decidedly lower profile than Gayle).

They have toured Italy, stopping to pick truffles in Umbria and go wine tasting in Tuscany and to meet the Italian premier. They have gone clubbing in Ibiza with will.i.am and music industry legend Jimmy Iovine. 

Oprah Winfrey herself has taken her entire staff on a vacation-turned-retreat to her Maui estate. Perhaps the most fabulous of all, a trip to Tahiti with the Obamas, Bruce Springsteen, which was topped off by cruises on David Geffen's luxury yacht. Don't ever tell Oprah she does not know how to let loose. 

With her decades-long career owner of a media agency and hosting a talk show, her giant bank account, her vacations and her homes, it is hard to think about what could be left for Oprah to dominate. She has started a new chapter and has turned her attention to dominate Hollywood. It is the perfect plan, really: When you are not in it for the money, a person can pick and choose from their passion projects and work to bring stories that they think are important to the big screen. 

Oprah Winfrey is no stranger to Tinsel town, having dabbled in producing and acting in everything from Lee Daniels' The Butler to Selma, but she has been turning to Hollywood with full force recently. It all started with a gig as executive producer of the scripted television series Queen Sugar, which follows siblings in a dispute over a family-owned sugarcane farm. The series aired on her eponymous network, but it was a gateway drug, if you will. 

Next was an acting gig in the HBO film The Immortal Life of Henrietta Lacks, which she also served as EP and which recounts the real-life story of an African-American woman who was used as an unwilling participant in medical studies (Oprah plays her daughter, Deborah, who is focused to right the injustice). And next spring audiences will see her starring in the big screen adaptation of A Wrinkle in Time, which recently shot in New Zealand alongside Mindy K aling and Reese Witherspoon. 

The flick was directed by Ava DuVernay, who told our team shortly after wrap time that while Oprah Winfrey was a fantastic addition to the cast, however, her most valuable contribution was the great party she threw for the entire crew, where she served up the margaritas herself.

Oprah Winfrey herself raved about the filming experience, telling our team that it was "one of the greatest experiences of her career." It seems that the acting bug has really set in, it was just announced that she will be starring in a reboot of Terms of Endearment. Billionaire or not, Oprah is not slowing down anytime soon.