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Former NYC Mayor Giuliani Sells Price-Reduced Manhattan Penthouse for $4.95M
To tell the truth, this does not seem like a successful real estate tale. The former mayor of the United States, Rudy Giuliani, just sold his penthouse on the Upper East Side for $4.95 million. It appears to be a luxurious offer in a famous Madison Avenue building. In actuality, it feels less like a victory lap and more like a clearance sale.
For years, the cooperative located at 45 E. 66th Street had been up for sale and down. In 2023, it was listed for $6.5 million, but bidders were uninterested. Following price reductions, withdrawals, and relistings, the ultimate discount brought it just under the $5 million threshold. Although the buyer’s identity is still unknown, his lawyer Gary Rosen confirmed the transaction.
Why is this important to me or to you? Since real estate is a representation of power, timing, and occasionally decline, it is more than just numbers. In 2002, while Giuliani’s power was at its peak, he once purchased this property. After twenty years, he is departing New York completely and giving up the keys for a price that speaks for itself.
Is this transaction more indicative of Giuliani’s decline in popularity or of the cooling luxury market in New York, in your opinion?
From $6.5M Dreams to a Clearance Sale
The pain of seeing a dream price gradually plummet is well known to anyone who has ever followed a real estate listing. That was the precise route taken by Giuliani’s apartment.
It was priced at $6.5 million when it first came out in 2023.Realtor was among the first to draw attention to that exorbitant price, and to be honest, it wasn’t an absurd amount for a co-op that was landmarked on the Upper East Side. The market, however, spoke. Buyers did not line up for months.
The property was relisted at $5.2 million by early 2025, and it eventually sold for $4.95 million. Consider that the original price was reduced by over $1.55 million. If you’ve ever sold a house, you understand how it feels to lose leverage in addition to money.
This indicates to me—and perhaps to you as well—that time is crucial, even in the premium market in New York City. The seller rarely has a good outcome from listings that linger, especially when there are legal issues involved.
This has happened before when famous mansions were listed at dream prices only to be later lowered. Take a peek at Emma Stone’s remodeled Austin home, which took several months and modifications before finding a buyer.
Inside the Stately Penthouse
Price by itself doesn’t reveal the complete story, so let’s take a moment to consider this. As you and I both know, homes are lived-in spaces rather than just statistics. Furthermore, Giuliani’s apartment wasn’t your typical co-op.
We are discussing more than 10,000 square feet on the top floor of the Fred Leighton Building, a structure that is a monument in and of itself. It has everything you could possibly want inside, including a formal dining room, a wood-paneled library, views of the city, and even a shrine of Yankees memorabilia that shouted “personal.”
Here’s the kicker, though. Although the location was prestigious, fashion is important. Parts of the d cor felt outdated, as noted by websites like Curbed, and seemed to be stuck in the early 2000s. Additionally, dating can be very expensive when buyers are spending millions of dollars.
I can’t help but wonder whether this property would have sold for more money at the initial listed price if Giuliani had updated the interiors. If the atmosphere felt outdated, would you still spend about $6 million on prestige?
It serves as a reminder that even the most prominent properties can be detracted by outdated interior design. Compare that to the $6.35 million sale of Julia Hough’s house in the Hollywood Hills, where modern improvements were a major factor.
Legal Shadows Over the Sale
The tale really takes off at this point. It would be impossible to discuss this penthouse without bringing up the lawsuits.
Do you recall Shaye Moss and Ruby Freeman? Giuliani falsely accused the Georgia election workers of tampering with ballots. He was found guilty of slander, and they were awarded $146 million. As part of that decision, a judge even ordered the confiscation of this apartment and other belongings.
Take a moment to consider that. Imagine having your house, where you’ve spent decades, almost taken away by a court order. Every time this penthouse was listed, that cloud lingered over it.
Giuliani was able to keep it after reaching a private settlement earlier this year. However, the harm had already been done. The property was now a legal headline rather than just a posh co-op. Buyers were aware of this.
Would you walk away from a property with this much baggage if you were the buyer? Please share your opinions here; I’d be interested in knowing what you think.
Divorce, Buyouts, and Financial Entanglements
In addition to the lawsuits, Giuliani’s private life was also involved in the transaction. In order to obtain complete ownership, he had to pay his third ex-wife, Judith, $2.5 million before the purchase was finalized. In exchange, she received property in Hamptons.
The pattern repeats as you go back further. In 2002, the year he formalized his divorce from his second wife, Donna Hanover, he paid approximately $4.8 million for the penthouse.
This flat is therefore more than just a financial asset. It has been used as leverage in a number of court settlements, divorces, and now a distressed sale. Giuliani’s co-op goes above and beyond the adage, “My home has seen everything.”
This raises the question of whether this location was ever really a home or merely a byproduct of a protracted conflict.
Florida Bound: From Central Park Views to Palm Trees
The last move is now. Giuliani is relocating to Florida as his primary residence, according to his lawyer. Only palm palms and the distance from the city he formerly ran remained, along with the vistas of Central Park and the grandeur of the Upper East Side.
This is more than just a relocation story to you and me. It is symbolic. After serving as America’s mayor in Manhattan, Giuliani became a divisive figure who fled south. The sale isn t just about money it s about leaving behind an era of power, reputation, and influence that once defined him.
I can t help but think: when you sell the home that carried so much history, are you closing a chapter, or running from it?
What s your take did Giuliani sell because he had to, or because he was ready to finally cut ties with New York?
By the way, I often share quick real estate updates and behind-the-scenes news on WhatsApp it s where you can catch stories before they hit the headlines.
What This Sale Says About NYC s Luxury Market
I don t know about you, but when I see a penthouse on Madison Avenue drop from $6.5M to $4.95M, I immediately wonder: is the luxury market softening, or was this just Giuliani s baggage dragging the price down?
Here s the thing. Upper East Side co-ops still command premium prices. Many listings above $5M do move, but only if they re updated and carry the right prestige. Giuliani s apartment had prestige, sure, but it also carried legal drama, dated interiors, and a seller who couldn t wait forever.
So what s the takeaway for you? If you re following NYC real estate, this is a reminder: even prime addresses aren t bulletproof. Buyers today are picky, and they d rather pay top dollar for something fresh than inherit a headline-making property with baggage.
And Giuliani s markdown isn t happening in isolation. Across the country, stars are rethinking their real estate strategies likeNick and Vanessa Lachey picking up Naomi Osaka s former LA homefor $8M, a deal that shows how prime properties still move fast when priced right.
What s Next for the Building and for Giuliani?
Here s where I always like to zoom out. The buyer of this penthouse hasn t been named yet, which makes me curious. Was it a private equity guy? An international buyer? Or maybe someone who saw an opportunity to own prime real estate at a markdown? Whoever it is, they re stepping into a building with history and high-profile neighbors.
As for Giuliani, the chapter closes with him in Florida. That s not just a change of address it s a statement. He s no longer tied to New York, no longer living in the shadow of Central Park. Instead, he s starting whatever s left of his public and private life in a state where many retirees go to disappear quietly.
And that s the bigger question you and I are left with: was this just a financial move, or the symbolic end of Giuliani s New York story?
What do you think did this sale mark the final break between Giuliani and the city that once defined him?
For more celebrity real estate stories like this one, check out ourReal Estate & Homeownershipsection.
Disclaimer:This article is based on publicly available reports, property records, and media coverage. It is intended for informational purposes only and should not be taken as legal or financial advice. All quotes and references belong to their original sources.
Table of Contents
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From $6.5M Dreams to a Clearance Sale
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Inside the Stately Penthouse
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Legal Shadows Over the Sale
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Divorce, Buyouts, and Financial Entanglements
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Florida Bound: From Central Park Views to Palm Trees
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What This Sale Says About NYC s Luxury Market
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What s Next for the Building and for Giuliani?
