Last year, the seal was cracked on Manhattan’s office market, and marquee deals flowed along prime turf such as Fifth Avenue. The party was still going strong in 2025.
Roughly one-third of the top 10 investment sales in 2025 in New York City were along fantastic Fifth. But the famed avenue cannot claim the biggest sale of them all — the purchase of 590 Madison Avenue by Scott Rechler’s RXR took that honor.
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Most of the big deals involved office properties, though there were prominent multifamily and retail trades. A school and an auction house got in on the action as well.
For instance, Miki Naftali bought 800 Fifth Avenue from Eliot Spitzer with plans to replace it. And Uniqlo tore a page from fellow Prada and Gucci parent Kering in recent years past, and bought its space at 660 Fifth Avenue. Plus, auction house Sotheby’s sold its longtime home at 1334 York Avenue to Weill Cornell medical school for $510 million (talk about a winning bid, huh? Huh?).
While the ball hasn’t dropped in Times Square just yet and some lucky brokers could close something big before that happens, the following are the biggest single-asset New York City investment sales of 2025, according to data from Cushman & Wakefield and Avison Young, plus reporting by Commercial Observer.
590 Madison Avenue
$1.08 billion
RXR spent months in talks with the State Teachers Retirement System of Ohio to buy the 42-story office property in the Plaza District, which ultimately traded in August for $1.08 billion — making it the biggest single office sale in New York City since 2022.
Executed with Elliott Investment Management as an equity partner, RXR stressed that the property would remain an office property, and would not follow the office-to-residential trend that hasn’t spared any corner of Manhattan.
RXR said the purchase supported its mission of shifting toward the best possible office assets as tenants continue to look for premium space to goad employees back to the office.
Eastdil Secured’s Will Silverman, Gary Phillips and Roy March brokered the deal. Apollo Global Management provided a $650 million acquisition loan to RXR.
800 Fifth Avenue
$810 million
When developer Miki Naftali closed on the $810 million purchase of 800 Fifth Avenue on the Upper East Side in August, it wasn’t quite clear what he had in mind for the 33-story, 208-unit multifamily tower.
But, by November, it became apparent that Naftali’s namesake firm planned to demolish the property — a move that at first seemed impossible given its protected status within the Upper East Side Historic District. But, the building had gone up in 1978, three years before the historic district was established by the Landmarks Preservation Commission.
Besides, 800 Fifth didn’t really follow the template of its forebears, and Naftali clearly saw an opportunity to add a design more in line with the character of the neighborhood.
Though the current rental building was valued at $1 billion, Naftali got a deal from the sellers and now plans to replace the structure once described by The New York Times as “a pitiful compendium of watered-down mannerisms” with luxury condominiums.
Newmark’s Jordan Roeschlaub and Nick Scribani negotiated $675 million in balance sheet financing for Naftali from J.P. Morgan Chase and Golden Tree, while Newmark’s Adam Spies and Doug Harmon arranged the sale of the property. The seller was Eliot Spitzer’s Spitzer Enterprises and Winter Properties.
1345 Avenue of the Americas
$644 million
Blackstone’s $850 million in commercial mortgage-backed securities financing for its 49 percent stake in Fisher Brothers’ 1345 Avenue of the Americas may have overshadowed the actual sales price.
For the record, Blackstone paid $644 million for the stake, according to Cushman & Wakefield, to get in on the action on the 50-story Class A office building in Midtown back in May.
Fisher Brothers had repositioned the building prior to the Blackstone deal. The move paid dividends. The 1.9 million-square-foot tower locked in the largest New York City office lease of 2023 when law firm Paul, Weiss, Rifkind, Wharton & Garrison inked a 765,000-square-foot deal.
An Eastdil Secured team of Grant Frankel, Ken Ziebelman and Ethan Pond arranged the CMBS financing from a syndicate led by Morgan Stanley.
1177 Avenue of the Americas
$572.3 million
A joint venture between Norges Bank Investment Management and Beacon Capital Partners dropped $572.3 million on 1177 Avenue of the Americas back in September, taking it off the books of Silverstein Properties and the California State Teachers’ Retirement System.
The buyers paid full asking price for the 47-story tower valued at $571.1 million with Norges taking a 95 percent stake, probably well worth the money with its location between West 45th and West 46th streets in the heart of the Bryant Park submarket.
Eastdil Secured’s Gary Phillips, Will Silverman, Sarah Lagosh and Alana Bassen negotiated the sale.
1334 York Avenue
$510 million
Weill Cornell’s medical school was the top bidder for Sotheby’s auction house at 1334 York Avenue, which it bought for $510 million in September as an extension of Weill’s Upper East Side campus.
While it wasn’t immediately clear how the property will be put to use, Weill Cornell hinted that it would become a patient care facility. Sotheby’s for its part had already planned a relocation to the Breuer Building at 945 Madison Avenue, which it purchased from the Whitney Museum of American Art in 2023 for $100 million.
Weill Cornell may not have to do too much moving around, either, considering it has leased space in the building since about 2023. David Giancola, Geoff Goldstein, Steve Klein, David Carlos and Joe Messina at JLL represented Weill Cornell in the sale. Doug Middleton, Lauren Crowley Corrinet and Mary Ann Tighe with CBRE represented Sotheby’s.
522 Fifth Avenue
$456 million
Amazon likely shelled out a little more than it needed to in May when it bought 522 Fifth Avenue from Aby Rosen and Michael Fuchs’s RFR Holding for about $456 million.
The e-commerce giant paid $106 million more than RFR purchased the 23-story Midtown office building for in 2020. The exact sale price remains a mystery. Property records note a $340 million trade — meaning an approximately $10 million loss for RFR — but sources told CO the trade was for $456 million.
Sources told CO that no brokers were involved and that Rosen negotiated the deal.
555-557 Broadway
$386 million
Publishing house Scholastic turned the page on its ownership of 555-557 Broadway, selling the 368,000-square-foot SoHo building to Empire State Realty Trust for $386 million in the waning weeks of 2025.
The leaseback deal will keep Scholastic in the 222,000 square feet it currently operates out of in the building. The company started in the summer looking for a buyer that would let it remain as a tenant while finding occupants for the three available floors. It appears to have made a hefty profit on the SoHo building, having acquired it in 2014 for $255 million.
Newmark’s Adam Spies, Josh King and Avery Silverstein represented the seller in the transaction.
660 Fifth Avenue
$355 million
The $355 million sale in the first quarter of the year of the retail portion of 660 Fifth Avenue to Japanese clothing retailer Uniqlo, where it operates a flagship store, continued a trend (if not put an exclamation point on it): retailers purchasing property they have traditionally leased, becoming owner-occupiers.
Luxury labels Prada and Kering (think Gucci and Balenciaga) kicked off the trend when they bought prime Fifth Avenue space from retail landlord Jeff Sutton for $1.8 billion around the start of 2024.
Uniqlo purchased the 90,732-square-foot retail space from Vornado Realty Trust and Brookfield Properties, which own the tower between 52nd and 53rd streets. The building is also known as 666 Fifth Avenue.
2 Grand Central
$273 million
Rockwood Capital sold 2 Grand Central Tower for $273 million.
Sovereign Partners, led by Darius Sakhai and Cyrus Sakhai, was the buyer, sources said. Eastdil Secured’s Gary Phillips and Will Silverman negotiated the sale, which closed Dec. 3 at $3 million above the building’s asking price.
The 667,000-square-foot asset at 140 East 45th Street rises 44 stories between Lexington and Third avenues, just half a block from Grand Central Terminal’s 45th Street entrance. It was constructed by Harry Macklowe in 1981, sold to BXP for $705 million in 2008, and then sold again to Rockwood in 2011 for $401 million. MetLife is the building’s existing lender and is providing roughly 65 percent — or $177 million — of the acquisition price in new financing.
560 West 43rd Street
$243.5 million
The last mammoth sale of 2025 was the first major non-office or non-retail one since 800 Fifth: The 44-story rental building at 560 West 43rd Street traded from investment manager Barings to J.P. Morgan Chase for $243.5 million in July.
Built in 1987 and known as Riverbank, the building has 418 apartments ranging from studios to three-bedrooms as well as 18,000 square feet of retail. JLL’s Jeffrey Julien described the sale as a fair-market deal at a price below replacement cost. He negotiated the sale along with colleagues Rob Hinckley, Andrew Scandalios, Steven Rutman and Devon Warren.
JLL’s Kelly Gaines, Geoff Goldstein and Michael Shmuely arranged $128.3 million in Freddie Mac acquisition financing.
