Five Expensive Buildings with Naughty Celebrity Stories

  Last modified on October 7th, 2021

The high life has its downs. And let’s be honest, it’s fun to read about local celebrities and their problems! Even if those problems may have arisen years ago. Here are some famous UWS buildings with some very naughty celebrity stories…

Fifteen Central Park West

Alex Rodriguez faced a rumored renting ban for having too many women coming in and out of his Upper West Side apartment. In 2014, The New York Post reported that A-Rod was accused of having prostitutes over a few times per week. And being unfriendly to staff in the building.

Naughty Celebrity Stories

photo credit: Keith Allison

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Harperley Hall

The co-op board at 41 Central Park West famously blocked pop star Madonna from buying a third apartment to expand her home. Madonna had previously purchased a second unit to expand her residence. She purchased the property years ago when married to actor Sean Penn.

The battle between Madonna and the co-op board went on for years. But in late 2018, Madonna was declared the loser.

Naughty Celebrity Stories

photo credit: chrisweger

220 Riverside Boulevard

In 2006, Gothamist reported that Donald Trump Jr. was ousted from the condo board at “Trump Place.” Trump Jr. was kicked off the board along with all existing members, after a resident filed petitions for their removal. Donald Trump Jr. was unable to fight the board because his father, now former President Donald J. Trump, was not the actual owner of the building. He simply rented his name to investors to attract tenants.

That plan stopped working, though, evidenced by the removal of his name from all UWS buildings.

Trump Jr. is also on his way out of NYC.

Naughty Celebrity Stories

photo credit: Gage Skidmore

The Dakota

Some of the most exclusive New York City apartments are located at The Dakota. The famous co-op at 1 West 72nd street has had a long list of “problems” starting with the murder of John Lennon just steps away from its doors. Application fees can soar above $1,000 and rejection is a high possibility. Celebrity applicants see as much rejection as unknown rich people.

According to the Real Deal, the co-op board at the Dakota faced a 2013 lawsuit from an African-American hedge fund executive for allegedly using racial slurs and denying an application for a second unit. Details about the settlement or pending status of the lawsuit were not disclosed.

The Dakota

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The Ansonia

The legendary former hotel has a surprisingly insane history. During the 1970s, the basement of The Ansonia was the meeting place for an infamous, members-only sex club called “Plato’s Retreat.” Members included celebrities, porn stars, and the well-to-do.

The Ansonia was also home to Babe Ruth, who reportedly walked around in his bathrobe and had wild parties in his apartment.

Well, things have seriously changed. Here’s another sex club that was based on the Upper West Side

The Ansonia

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