Despite cities taking a back seat to vacation markets in 2021, major transactions made headlines across New York, Miami and Los Angeles.

October is Luxury Month at Inman, and this is the fourth in a 5-part series looking at the high end market. Check back tomorrow for the biggest overall luxury sales of 2021, and click here to read how the luxury housing market became invincible in 2021, here to see the biggest luxury mountain sales and her to see the biggest luxury beach sales. Then join us for Luxury Connect at the Aria Hotel (Oct. 25-26, 2021) and the live presentation of the Inman Golden I Club honorees for this year.

While big city living is coming back in full force, the most expensive sales of 2021 still show that cities have taken a back seat compared to the kind of money being spent on property in vacation markets like Palm Beach and the Hamptons. The reverberations of the pandemic, in which anyone with money to spend was looking for a larger house away from the crowded city, are still being felt in the market today.

That said, there have certainly been a number of pricey sales in cities like New York and Los Angeles. The most expensive real estate transaction of the year took place, in fact, when Alibaba co-founder Joe Tsai paid a combined $157 million for a pair of adjoining 220 Central Park South condos.

Traditionally, home values and geographic distribution of wealth meant that compilations of this sort were almost exclusively dominated by New York and Los Angeles, but Miami has recently been pushing other big sales out as demand for South Florida homes skyrocketed amidst the pandemic.

Without further ado, here are the biggest city sales of the year.

220 Central Park South

$157 million

New York, New York

City Realty | Wikipedia | Alibaba

The most expensive real estate purchase (both overall and for urban real estate) was cemented not by a flashy celeb but in great secrecy by the founder of e-commerce giant Alibaba.

Taiwanese-Canadian investor Joe Tsai, who also owns the Brooklyn Nets, paid a combined $157 million for a pair of condos in one of New York City’s most sought-after addresses. The condos include a full-floor, 5,935-square-foot unit on the 60th floor that Tsai bought for $82.5 million, another full-floor unit on the 61st floor for $57 million and an 18th-floor studio for Tsai’s staff.

While news that someone had made one of the largest real estate purchases in New York’s history (the biggest in both the city and the country is still held by Ken Griffin, who bought the penthouse in the same building in 2019 for $238 million) had first broken in June, Tsai’s identity as the buyer was not revealed until late July.

The purchase is around the same price range as the biggest real estate sale of 2020, which occurred when Jeff Bezos shelled out $165 million for a historic Los Angeles property known as Warner Estate.

141 South Carolwood Drive

$88 million

Los Angeles, California

Alexis Adams

A long-running real estate saga finally came to an end when Owlwood Estate, an ostentatious Los Angeles mansion once owned by 1960s icons Sonny and Cher and later tied to disgraced developer Robert Shapiro, sold to an unidentified buyer.

The house comes with a rich history — 20th Century Fox co-founder Joseph Schenck bought it from its first 1930s owners and would use it to host parties frequented by stars like Marilyn Monroe.

In the 1960s, Cher also came to a party on the grounds and liked the estate so much that she convinced actor Tony Curtis to sell it to her. She and husband Sonny Bono lived in it throughout the late 1960s and early 1970s.

While the Tuscan-style mansion is beautiful and an important part of Hollywood history, it has also become inextricable from controversy in recent years. Shapiro, who was sentenced to a 25-year prison sentence for running a Ponzi scheme with investors, had bought Owlwood for $90 million in 2016. In 2019, he was found guilty of defrauding investors out of more than $1.3 billion.

Viewpoint Collection Partners investment group then took control of Owlwood on behalf of Shapiro’s victims and had been trying to sell it, cutting prices several times, since then.

535 Barnaby Road

$70 million

Los Angeles, California

Simon Berlyn | Zillow | Wikipedia

The biggest celebrity purchase of the year took place when Abel Tesfaye, known professionally as best-selling musician The Weeknd, paid $70 million for a 1.6-acre estate in the flashy Bel Air neighborhood.

More of a resort than a house, 535 Barnaby Road comes with a spa with a sauna and a hammam, indoor and outdoor pools, a sports court, a gym, movie theater and a music studio.

The owners, Dutch media mogul-producer Reinout Oerlemans and his wife Danielle Oerlemans, were not looking to sell but the famous singer took interest in the house and got local celeb agents Rayni and Branden Williams to approach the couple about a potential sale, which took place in an off-market deal with Angel Salvador of the Beverly Hills Estates representing Tesfaye.

The Oerlemans did not exactly come out of the deal homeless or with a bad deal — they purchased the house for $21.44 million in 2015 and made nearly $50 million in profit. Over the time they spent living in the property, the couple undertook a massive renovation that added around 13,000 square feet to the existing structure and reworked the interior to an open floor plan.

2188 Mandeville Road

$65 million

Los Angeles, California

2188 Mandeville Canyon Road

Music and media mogul Scooter Braun, manager to stars like Justin Bieber and Ariana Grande, dropped $65 million on a 19,000-square-foot spec home in LA’s Brentwood neighborhood at the start of September.

Sitting on four acres of land and made out of stone, the estate was a collective effort to outdo other ostentatious mansions that LA is so known for. Architect Noah Walker, interior designer Jamie Bush and landscape artist Christine London all contributed to bringing it to fruition. Other amenities include a billiards room with a wet bar, a 1,650-bottle wine room, a covered patio with a full kitchen and two 75-foot pools.

Blair Chang of The Agency was the listing agent representing the property while Josh and Matt Altman of The Altman Brothers Team at Douglas Elliman represented the anonymous buyer.

The sale is the biggest in Brentwood’s history and the second-biggest real estate transaction in LA’s Westside in 2021 so far.

1101 N. Beverly Drive

$63 million

Los Angeles, California

Amalfi Estates

Another long real estate saga came to an end when Hearst Estate, a 3.5-acre Spanish-style estate with a storied Hollywood history, sold after 14 years in the market and over $120 million in price cuts.

After filing for Chapter 11 bankruptcy, attorney and last owner Leonard Ross had been trying to sell 1101 N. Beverly Drive since 2007 but struggled to find someone willing to take on its high level of debt.

Ross had initially listed the home for $195 million, but it was eventually seized by a bankruptcy court that then took on a series of aggressive price cuts.

The listing price was slashed to $119 million only to be relisted again for $90 million in April, $70 million in June and $50 million in July. Last week, news broke that Los Angeles-based investment company Berggruen Holdings had agreed to pay $63 million (initially reported by news outlets to be $47 million) for the eight-bedroom, 15-bathroom property in a highest-bidder auction that received multiple offers.

Had it not been for the default property taxes (that will be paid in escrow as part of the contract), the property would have been a much more valuable sale due to its large size and connection to Hollywood history.

2 East 88th Street penthouse

$60 million

New York, New York

2 East 88th Street | CityRealty

The record for the biggest amount of money ever paid for a New York co-op was set in May when Swiss financier Jacqui Safra sold his triplex penthouse at 2 East 88th Street for $60 million. Unique to New York City real estate, a co-op is a building that functions as a corporation and “allows” those it deems worthy to buy shares in the building.

A 12-room unit taking up the 14th, 15th and 16th floors of the building, the extravagant penthouse was on the market for only one day when it sold to an unidentified buyer. The deal was kept tightly under wraps and news of the sale did not come out until September.

At 81 years old, Safra spent decades living in the apartment with his producer partner Jean Doumanian but ultimately decided to sell. Nikki Field of Sotheby’s worked with him and said to have showed it to seven different buyers before it was accepted.

11 East 69th Street

$57.5 million

New York, New York

11 East 69th Street | Google Maps

The biggest townhouse sale of the year was actually not the 28,000-square-foot townhouse that was raided by the FBI when Jeffrey Epstein was arrested in 2019 (listed below) but a smaller townhouse that L&L Holding CEO David Levinson sold in March for $57.5 million.

Located at 11 East 69th Street, the house had belonged to Levinson and his wife Simone since they bought it for $9.5 million in 2004. It sits at 6,352 square feet and six stories and has undergone a massive renovation to modernize it — it was first built in 1924 as an office building.

Adam Modlin of the Modlin Group represented the Levinsons, who were at least partially pushed into selling by the high costs of taxes and maintenance.

“The couple were self-shopping the mansion for a while,” an anonymous source told the New York Post. “Like many people, they wanted to leave New York during the pandemic, and there was also a tax incentive to leave.”

67 Beverly Park Crescent

$51 million

Los Angeles, California

Concierge Auctions

California mansion that was once listed for $165 million sold to the highest bidder following an auction in February for $51 million — more than $110 million below the original asking price.

The 28,000-square-foot estate at 67 Beverly Park Crescent is known as Villa Firenze and was built in 1998 to look like an old European palace. It boasts 13 bedrooms, 17 bathrooms and opens onto a palm-lined courtyard that can fit up to 30 cars .

Hilton & Hyland’s Jeff Hyland and Rick Hilton were the listing agents for the home while it was on the market. After failing to find a buyer to pay the exorbitant price for more than three years, billionaire owner Steven Udvar-Hazy, the executive chairman of Air Lease Corporation, turned to Concierge Auctions to organize an auction in December.

While the sales price is significantly below what Udvar-Hazy had been hoping to get for it, it still set the record for the most expensive property ever sold at auction; another palace-style estate that sold for $42.5 million in Hillsboro Beach, Florida in late 2018.

56 Leonard penthouse

$50 million

New York, New York

Credit: Max Pixel

In August, the top unit of 56 Leonard in New York’s Tribeca sold for $50 million to an unidentified buyer. Nicknamed the “Jenga Tower” for the way the condos resemble stacked boxes in the sky, the 60-unit tower was completed in 2017 and has sold its 45 units for between $3.5 million and now $50 million.

The penthouse sits at 7,779 square feet and has 19-foot ceilings, white oak and stone floors and three terraces at 1,252 square feet overlooking the New York Harbor.

The same penthouse last sold for $47 million in 2013 to a hedge fund manager and now sold for the same price it was listed for eight years ago. While the pricing indicates the different rhythm (ultra-high-end properties do not always go up and up) of the luxury market, the sale is still the most expensive real estate transaction in downtown Manhattan this year.

9 East 71st Street

$50 million

New York, New York

Modlin Group | WikiPedia

Two years after convicted pedophile Jeffrey Epstein committed suicide while waiting for trial, his 28,000-square-foot townhouse at 9 East 71st Street entered contract to sell for $50 million in March.

Once the epitome of luxury, the house became the site of a police raid in which photos of underage girls, piles of cash, diamonds and an expired passport listing Saudi Arabia as Epstein’s residence were uncovered after Epstein was arrested in 2019.

The sale of both the townhouse and a nine-bedroom waterfront estate in Palm Beach are part of a victims’ compensation fund that a judge and Epstein’s estate negotiated for his victims. The property on East 71st Street originally listed for $88 million with Adam Modlin of the Modlin Group, and later had its price lowered to $65 million before being sold for $50 million.

67 Vestry

$45 million

New York, New York

67 Vestry | CityRealty

The penthouse of 67 Vestry, a 13-unit waterfront condo building in Manhattan’s Tribeca neighborhood, entered contract to sell for around $45 million in September.

While few details exist about the sale, the building now housing ultra-luxury condo units was once used as the warehouse for the Great Atlantic & Pacific Tea Company. Its biggest attraction is its location downtown (the units, and in particular the penthouse, offer panoramic views of the New York Harbor) but as the structure is on the older side, it is currently undergoing a massive renovation and expansion that will add several stories to the building.

Iliad Realty Group, which purchased the building for $55.5 million in 2017, is overseeing the development while Corcoran Sunshine Marketing Group is the sole real estate company overseeing the sales.

295 Lafayette Street

$42.5 million

New York, New York

Zillow

A year after selling their New York City pad and taking off to Miami, real estate heir Joshua Kushner and supermodel Karlie Kloss moved back into a $42.5 million penthouse atop 295 Lafayette Street in Nolita. At the start of September, the couple entered contract to buy the condo, which had previously listed for $42.5 million.

The entire building was developed by Kushner Co., the real estate company once led by Kushner’s brother and former President Donald Trump’s son-in-law Jared Kushner. Known in the building as Penthouse #1, it boasts more than 7,200 square feet, plus 5,100 is outdoor terrace and balcony space).

Adam Modlin of the Modlin Group worked with Kushner and Kloss. First listed for $66 million in 2015, the apartment was on the market for $42.5 million in March 2019. It has reportedly been rented out for $1.25 million a year at some point during that time period.

5800 North Bay Road

$40 million

Miami, Florida

Nelson Gonzalez Realty

Most Miami mansion sales fall simultaneously into both the “city” and “beach” categories. In August, famed “Genesis” drummer Phil Collins sold his Biscayne Bay mansion that was once listed for $40 million.

While the exact sale price has not been made public, the 10,769-square-foot, Mediterranean-style estate had been on the market for just over a month until a buyer whose identity was protected by an LLC scooped it up.

The home has 184 feet of waterfront overlooking Miami’s Biscayne Bay, while a private dock, pool, spa, 6,000-gallon koi pond, summer kitchen and cabana give it the feel of a tropical resort.

And while Collins is a celebrity himself, the buyer of the home will have even more bragging rights — Jennifer Lopez owned it from 2002 to 2005 before selling it to businessman Mark Gainor.

Jill Hertzberg, of the Jills Zeder Group at Coldwell Banker held the most recent listing.

46 Star Island Drive

$39 million

Miami Beach, Florida

46 Star Island Drive | Realtor.com

Built in 1926, Miami Beach’s 46 Star Island Drive has been an iconic property for almost 100 years now When Florida entrepreneur Carl Fisher built the 20,000-square-foot mansion in 1924, nothing quite so grand existed in the area.

It is, of course, grand by today’s standards as well: a Mediterranean-style villa with 40 rooms, 12 bathrooms, 250 feet of water frontage and a private dock.

Originally listed for $65 million in 2016, the home has been on and off the market since then. At one point, it even went to auction but, after the sale fell through, went back on the market for $42 million in 2018.

Alexa Eve Iacovelli and Dora Puig of Luxe Living Realty held the listing for seller Marco Iacovelli, father of agent Alexa Eve and founder of Miami-based Rally Manufacturing.

53 West 53

$35.5 million

New York, New York

StreetEasy

At the end of September, the penthouse unit in the glass skyscraper above New York City’s Museum of Modern Art entered contract to sell. While both the identity of the buyer and the final asking price have been kept tightly sealed, the 4,928-square-foot likely sold for somewhere around its asking price of $35.5 million.

While the world-renowned museum and a restaurant are located on bottom floors adjacent to the building, the 1,050-foot-tall 53 West 53 was designed by Jean Nouvel to primarily feature luxury living units. The penthouse floats nearly 900 feet above the ground. Building residents also have access to a gym, a 65-foot pool, a sauna, a golf stimulator, a squash court along with numerous libraries and wine tasting rooms.

The listing was shared by Douglas Elliman’s Shari Scharfer Rollins, Frances Katzen, Jade Chan, Matthew MacKay, Fredrik Eklund and John Gomes.

1 Star Island Drive

$35 million

Miami, Florida

Realtor.com | Getty Image,

Another major Miami sale took place when singer-producer duo Emilio and Gloria Estefan sold their mansion for $35 million. Located in the gated Miami community of Star Island, the 58,000-square-foot estate sits on over an acre of land overlooking Biscayne Bay and is built in the style of a Floridian villa.

Almost every room in the house has views of the MacArthur Causeway and Miami skyline. Once again, Jill Hertzberg and Jill Eeber of Coldwell Banker’s Jills Zeder Group represented the property while Compass’ Todd Nordstrom worked with the anonymous buyer.

Due to its proximity both to Miami and the water, 1 Star Island Drive is at once a beach and city sale. The deal closed in late July and is indicative of Florida’s fast-growing real estate market as more people chose to move there to be in a warm climate during the pandemic.

In Miami, home prices grew by 46 percent between summer 2020 and now. The Estefans bought this property in 1993 for $1.84 million and, wanting to sell for a while now, first listed it in 2015 for $40 million and then again in 2019 for $35 million.

3323 Devon Court

$33 million

Miami, Florida

3323 Devon Court | Realtor.com

Real estate folks in South Florida will have surely heard of Argentine-American “condo king” Jorge Perez. Known for developing over 90,000 buildings in Miami over his 40-year career, Perez sold his own 3323 Devon Court property to cannabis executive Jonathan Sandelman and his wife Alicia Bona Sandelman for $33 million in September.

The price is exactly what Perez asked for the property. The 10,000-square-foot house is known as “Villa Cristina” and is located in the Hughes Cove gated community of Miami’s Coconut Grove. It is built in the style of a Venetian Palazzo and has 482 feet of water frontage, overlooking Biscayne Bay.

Also well-known real estate names in Miami, Jill Hertzberg and Jill Eber of the Jills Zeder Group at Coldwell Banker had this listing while Lisa Sayfie of Compass worked with the Sandelmans.

With a net worth of over $2 billion, Perez chose to gift the proceeds of the sale to the Miami Foundation, a nonprofit that connects wealthy donors to local causes.

220 Central Park South

$33 million

New York, New York

Courtesy of 220 Central Park South

Another condo from the storied 220 Central Park South made our list of the biggest sales in the city. This four-bedroom, 3,703-square-foot unit on the 31st floor was listed with Manju Jasty of The Corcoran Group and handed over to an unknown buyer for $33 million.

Having bought the unit for $26.2 million in 2018, Arel Capital founder Richard Leibovitch made nearly $7 million in profit within three years. The sales price is slightly below the $36 million asking price. When the property sold in September, it had been on the market for more than a year.

217 West 57th Street

$28.5 million

New York, New York

Getty Images

A 93rd-floor unit atop the world’s tallest residential building has sold for $28.5 million just a few weeks ago. Located at 217 West 57th Street in Manhattan, Central Park Tower was fully completed in 2021 by Adam Smith + Gordon Architecture and is currently the second-tallest skyscraper in the U.S.

Buyers Cindy K. Chan and Hung P. Wong paid $10 million below the $38.5 million asking price for a four-bedroom, 4-and-a-half bathroom unit in an off-market deal.

The supertall skyscraper tops off at 1,550 feet and 136 stories and was built over the course of five years. Building amenities include an outdoor terrace with a pool, screening room, private elevators and a children’s playground

11507 Orum Road

$27.5 million

Los Angeles, California

Redfin | Wikimedia

Another big celebrity purchase took place at the very start of the year when late-night talk show host and comedian Trevor Noah paid $27.5 million for 11507 Orum Road, a Bel Air mansion designed by American Institute of Architects fellow Mark Rios.

Designed to look like a traditional Japanese home, the 11,000-square-foot mansion has six bedrooms, 11 bathrooms and amenities like a rooftop terrace, a chef’s kitchen, a library made to look like an ancient Kyoto study room and a spa.

The property, which Rios designed after the previous structure on the lot was razed, first hit the market in 2018 for $36 million. The most recent asking price before Noah’s purchase was $29.5 million.

Noah sold another mansion in Bel Air property for $21.7 million in September and also owns a 3,596-square-foot apartment in Midtown Manhattan, a short subway ride from Comedy Central’s studios. Hilton & Hyland’s Linda May and Drew Fenton were the listing agents.

Email Veronika Bondarenko

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