Jake Gyllenhaal Sells Apartment Inside Celebrity-Loved ‘Paparazzi-Proof’ Building in New York for $14 Million

Actor Jake Gyllenhaal has offloaded his stunning Tribeca condo for $14 million—providing one lucky (and very wealthy) buyer with the opportunity to rub shoulders with a host of celebrities who also call the paparazzi-proof apartment building home.

The “Prisoners” star landed a buyer for his pad at 443 Greenwich St. in an off-market deal, as first reported by The Real Deal.

Gyllenhaal purchased the abode in 2017 for $8.63 million, joining other A-listers who have owned properties in the building over the years, including Jennifer Lawrence, Blake Lively and Ryan Reynolds, Harry Styles, Mike Myers, Justin Timberlake, and Lewis Hamilton.

The building, which was built in 1882, also houses Jennifer Gates, a daughter of Bill Gates and Melinda French Gates. The billionaire co-founder of Microsoft had purchased the unit from Formula One driver Hamilton in 2023 for $51 million.

The building at 443 Greenwich St. has become a hot spot for A-listers due to its extreme privacy. Often described as being “paparazzi-proof,” the building is a haven for stars seeking safety from prying eyes.

Among the building’s many safety features are an underground entryway and private elevators that access the units, ensuring that residents can come and go as they please without having to interact with their neighbors.

In keeping with that theme, many of the units in the former bookbinding factory are registered to LLCs and trusts, as is the case with Gyllenhaal’s former property, which was purchased through a limited liability company that is connected to an address in Los Angeles.

It is unclear where the actor, who recently starred in Broadway’s “Othello” with Denzel Washington, is currently living. Though he holds the keys to a Hollywood Hills home, he spends the majority of his time on the East Coast.

Gyllenhaal’s former unit is situated on the fifth floor and sprawls across 2,868 square feet.

It boasts three bedrooms, three bathrooms, a chef’s kitchen, and an open floor plan.

The building provides a 24/7 door attendant, 24/7 concierge service, and a live-in building manager, among many other amenities.

It also boasts a 71-foot indoor pool, a 5,000-square-foot roof terrace, a 4,000-square-foot landscaped courtyard, a gym, a locker room, and a Turkish bath.

While the building prides itself on its discretion, its board has found itself embroiled in a recent controversy.

Gyllenhaal’s sale comes hot on the heels of news that the building’s condo board is suing its developer, Nate Berman’s Metro Loft, and its architect, CetraRuddy, for $376 million.

The lawsuit filed in 2021 by 443 Greenwich St. alleges breach of contract, construction defects, and code violations—all allegations denied by the developer and architect. The lawsuit is ongoing.

It was also dragged into another scandal last year, when one of its residents, actress Blake Lively, became embroiled in a bitter lawsuit against fellow actor Justin Baldoni, which saw the latter recounting an awkward encounter he had with Lively in her residence in the building.

In a 179-page complaint filed at the end of 2024, he laid out a series of allegations against Lively and her husband, Reynolds, including one claim that he was “pressured” into accepting changes to the “It Ends With Us” script that had been made by the actress during a visit to her Tribeca home.

According to Baldoni, he was “summoned” to the couple’s New York City apartment to discuss changes that Lively had made to a specific scene in the movie, which takes place between the two lead characters on a rooftop. The actor and director says that when he arrived at the home, he was greeted by Reynolds, who immediately began heaping praise on his wife’s script updates.

“As the meeting was ending, a famous, and famously close, friend of Reynolds and Lively, walked into the room and similarly began praising Lively’s script,” the lawsuit states, according to CNN. “Baldoni understood the subtext: he needed to comply with Lively’s direction for the script.”

Baldoni claims that he later sent Lively a text message to reiterate his appreciation for the changes that she had made, adding that he “would have felt that way without Ryan and Taylor,” and that he was “excited and grateful” to be working on the project with her.

His reference to “Taylor” has led many to believe that the person in question is pop star Taylor Swift, who is a close friend of Lively and Reynolds.

The couple’s apartment is mentioned again in the lawsuit, when Baldoni says that Reynolds “swore at [him] and accused him of fat-shaming his wife” while the director was paying a visit to the abode.

Baldoni’s lawsuit was dismissed in June of this year; however, the legal battle between the two on-screen stars is ongoing.