Inside the Secretive World of Celebrity Real Estate—and How Stars Hide Their Multimillion-Dollar Deals From Prying Eyes

When they’re not lighting up the stage or screen, many of Hollywood‘s biggest stars turn their hands to another very lucrative endeavor: real estate investment.

To look at any one of the entertainment industry’s best and brightest is—more often than not—to look at a veritable property mogul with a portfolio that is filled with some of the country’s most enviable homes.

TV mogul Oprah Winfrey, for example, boasts a collection of properties across the U.S. that are worth an estimated $150 million, while comedian Ellen DeGeneres has bought, flipped, and sold dozens of homes over the past decade alongside her wife, actress Portia de Rossi.

But unlike the average homeowners, these elite A-listers conduct their real estate investments behind a shroud of secrecy, going to great lengths to protect their privacy—and keep their homes away from the prying eyes of fans.

Enter the off-market deal, a tactic that is regularly used by celebrities and other high-profile property owners to buy and sell homes behind the scenes, ensuring that details of their activities are kept as secret as possible from the outside world.

On any given day, a new story will emerge about a celebrity who has bought or sold a home “off-market,” meaning that the dwelling was never listed with an MLS, with negotiations and offers taking place in secrecy—kept hidden from the public until the sale has closed.

Celebrity real estate agent and “Selling the City” star Eleonora Srugo says off-market deals are becoming increasingly popular among her wealthiest clients, revealing that neither of the last two properties she sold was publicly listed.

It has been suggested that these off-market deals are used to boost a home’s feeling of exclusivity and luxury, while others believe that these secretive sales allow for a property to be sold at a higher price than it might be if it were publicly listed, because it prevents true transparency as far as home values are concerned.

However, according to real estate agent Cara Ameer, who is based in California and Florida, this tactic is most often employed because it helps to protect the privacy of whichever high net worth individual is trying to buy or sell a home, enabling them to avoid splashing images of their interiors across the internet for people to analyze and critique.

An off-market deal is of even greater importance to a celebrity if their home sale might give away details about their personal lives, she adds, particularly when it comes to a divorce or separation.

“Celebrities prefer to sell off-market due to privacy, safety, and security,” she explains. “They may be going through a personal situation, and so they don’t want the media getting wind of them putting their home on the market. 

“This is often the case with divorces, breakups, and lawsuits. When celebrity homes are listed, they are emptied out of any personal belongings [that might link] them to [their A-list owner]. This is also due to potential security breaches—no one wants to expose their luxury décor and belongings for all to see.”

What’s more, an off-market sale often makes it harder for someone to track down a home’s owner, especially if those involved in the deal have conducted their business through an LLC or a business manager.

“The title is typically held in a trust or an LLC, [and] you would have no idea who is behind that without doing some really deep digging,” Ameer explains.

“The address on the tax record might be that of a business manager or wealth adviser so as to put another wall between the name showing on the title and the address.”

If a celebrity is buying a home, they will often send employees to scout their chosen locations to ensure that the property suits their standards before they agree to view it themselves, Ameer says. Some might even purchase a dwelling without ever setting their own eyes on it to avoid risking their business becoming public knowledge.

“There are typically nondisclosure agreements to be signed that are required of agents representing properties that celebrities want to see, as well as the agents representing those celebrities looking to buy,” she went on.

“The owner of the home may also be required to sign one that prohibits any of these parties from disclosing any information about who is showing the home.”

While off-market deals are becoming more frequent among the world’s wealthiest homebuyers and sellers, they are by no means a new tool. Many celebrities have relied on such deals over the years to keep their personal business personal.

Take, for example, one of the world’s most famous women, Taylor Swift, 35, who has gone to great lengths to conceal her real estate dealings from her hordes of fans, securing multiple properties in off-market deals, including two New York City abodes.

While some details of the homes—one, a townhouse, and the other a $9.75 million Tribeca loft—have been revealed, no interior images have ever been shared because the properties were never publicly listed, affording the pop star at least a small piece of privacy.

Comedian-turned-real estate mogul DeGeneres, 67, and her wife, de Rossi, 52, have bought and sold multiple homes in the greater Los Angeles area over the last decade, many of which were secured in off-market deals.

One of her most lucrative deals to date involved the sale of an enormous blufftop estate in Carpinteria, CA, which was purchased for $96 million by billionaire Robert Friedland in an off-market deal in 2024.

The sale was part of a very secretive property swap, which saw DeGeneres and de Rossi—who relocated to the U.K. at the end of 2024—buying back a $32 million home that they had previously sold to Friedland just months earlier.

Then there’s pop star Justin Bieber, 31, and his wife, Hailey Bieber, 28, who secured themselves a dazzling $16.6 million vacation home in Palm Springs, CA, in 2023. This off-market purchase was not publicly revealed for close to a year.

Clint Eastwood, 94, sold his longtime home in Pebble Beach, CA, in an off-market deal in 2017, having owned the property for more than 20 years.

As first reported by Variety, the Spanish Colonial mansion was being shopped around to a handful of lucky buyers for $9.75 million, having been purchased by the Hollywood legend for $3.9 million through a real estate trust in 1994.

“Pretty Woman” star Richard Gere, another celebrity who has quit the U.S. in favor of moving abroad, prepared for his relocation by offloading his stunning six-bedroom, 11-bathroom New Canaan, CT, home for $10.75 million in an off-market deal in 2024.

The 75-year-old actor had originally purchased the home from singer Paul Simon in 2022 and had intended to turn it into a working farm, before deciding to move to Spain, where his wife, Alejandra, is from.