By: Russ Spencer

He may be 88, but real estate titan Harry Macklowe is once again rewriting the skyline — this time not through soaring towers, but through the reinvention of a historic Upper East Side address. The legendary developer has finalized a $49 million deal to redevelop the 1920s limestone-and-brick building at 809 Madison Avenue, transforming the landmark corner of Madison and East 68th Street into a boutique collection of sprawling, high-end condominiums.

According to a report that appeared in late September at The Real Deal, the transaction marks Macklowe’s return to his first love — New York luxury real estate — and signals his unrelenting appetite for ambitious design projects even as he nears 90. The property, long viewed as a redevelopment challenge due to its location within the Upper East Side Historic District, has sat vacant for years, deterring potential developers wary of navigating the city’s preservation bureaucracy. But Macklowe, whose career has been defined by boldness and an eye for reinvention, has reportedly secured the approval of the Landmarks Preservation Commission (LPC) to expand and modernize the building while maintaining its architectural integrity.

As The Real Deal report detailed, Macklowe plans to convert the structure into a limited number of expansive single-floor residences, each averaging 4,000 square feet. The design includes three new floors atop the existing roofline, a horizontal expansion along the eastern elevation, and larger windows that will bring in more natural light. Atop it all will sit a 1,500-square-foot penthouse terrace, offering panoramic views of Manhattan’s “Gold Coast.”

The project’s design team reads like a who’s who of contemporary architecture and development. Macklowe has partnered with Abe and Scott Shnay of SK Development, with the conversion to be helmed by Robert A.M. Stern Architects and SLCE Architects, both of which have shaped some of New York’s most celebrated residential buildings.

Apartments are expected to command more than $20 million each, positioning 809 Madison among the city’s most exclusive boutique developments. “This is exactly the kind of project Harry loves — small, complex, historic, and very, very high-end,” one industry source told The Real Deal, noting that Macklowe’s patience with the landmarking process and his deep relationships with city agencies likely proved decisive in advancing the plan.

The purchase of 809 Madison from Churchill Real Estate Holdings was orchestrated through Avison Young, whose U.S. Investment Sales team — led by Principal James Nelson and directors Alexandra Marolda, Brent Glodowski, and Eric Karmitz — represented the seller. In a statement on the Avison Young web site, Nelson said, “We’re pleased to achieve a successful outcome for our client and the local community, which will see a historic property that has long sat vacant be repositioned for the future.”

The sale included the building’s residential portion; Churchill had earlier sold off the retail component to the Jackson Group for $9 million in 2024, following its $55 million acquisition of the property in 2019. Retail expert, and real estate visionary Isaac Chehebar is the principal at Jackson and his stellar reputation in the field is legendary. Nelson described the corner asset as “a prime Madison Avenue and East 68th Street location offering value-add opportunities in one of the world’s premier residential and retail shopping corridors.”

Financing for the redevelopment involves a sophisticated capital stack befitting Macklowe’s reputation for complex dealmaking. According to the information provided in The Real Deal report, construction financing was arranged by Infinite Global Partners, led by former Silverstein Properties CEO Marty Burger, alongside the Related Funds. Sculptor Capital Management and Circle Property Partners are providing preferred equity, while a group of family offices and ultra-high-net-worth investors are participating as limited partners. The financing package was structured by Michael Campbell of the Carlton Group, a veteran of many large-scale New York property transactions.

809 Madison’s transformation comes at a time when Upper East Side redevelopment is experiencing a quiet resurgence. As The Real Deal has reported, the corridor north of 60th Street is seeing renewed interest from investors seeking to reposition aging prewar buildings for a new generation of affluent buyers. The area, long synonymous with old-money elegance, is now embracing modern luxury as developers like Macklowe infuse historic properties with new vitality.

YIMBY, which first published renderings of the redevelopment in September, described the expanded 159-foot-tall structure as one that “marries historic preservation with modern opulence.” For Macklowe, who once reshaped Midtown with glass towers like 432 Park Avenue, this project represents a subtler but equally ambitious expression of architectural craftsmanship — a project where scale gives way to refinement.

As The Real Deal report observed, this marks Macklowe’s first major New York development launch in nearly a decade. His last transformative project, the $2 billion conversion of One Wall Street, remains one of the most ambitious adaptive reuse efforts in Manhattan history. Purchased for $585 million in 2014, the Art Deco skyscraper was transformed into luxury condominiums and retail, a project that weathered market fluctuations and early sales challenges but ultimately found footing amid renewed downtown demand.

Despite scaling back some of his other projects — including selling a Midtown office building that was once part of his grand “Tower Fifth” supertall plan — Macklowe remains one of New York’s most recognizable figures in real estate. In recent years, his name has surfaced not only in connection to major deals but also through headline-making personal and legal battles.

In 2018, his high-profile divorce from Linda Macklowe captivated tabloids, even as he continued to navigate litigation with partners such as CIM Group over the operation of 432 Park Avenue. Earlier this year, The Real Deal reported that Macklowe filed suit against the Israel Discount Bank of New York to block foreclosure proceedings tied to his stakes in a pair of real estate investment trusts.

And in Florida, Macklowe has joined forces with Jorge Pérez’s Related Group on a two-tower condominium development in North Bay Village, suggesting that his appetite for new ventures remains undiminished by age or controversy.

Industry observers quoted in The Real Deal report suggested that Macklowe’s return to Madison Avenue reflects not nostalgia, but a calculated reading of the market. The first half of 2025 saw a 13.3 percent uptick in multifamily investment transactions nationwide, totaling more than $2.4 billion across 205 deals, according to data from Avison Young. In New York, the combination of low inventory, limited new land supply, and surging demand for historic conversions has drawn investors back to legacy neighborhoods such as the Upper East Side.

For Macklowe, the 809 Madison Avenue redevelopment is emblematic of a new kind of luxury — one rooted not in height but in heritage. “The buyers he’s courting want exclusivity and architectural pedigree, not sheer scale,” a veteran broker told The Real Deal. “This is where the top of the market is right now — quiet, understated, and exquisitely crafted.”

As construction begins on 809 Madison Avenue, the aging developer appears as energized as ever, pursuing one last architectural masterpiece in the city that has defined him. The limestone façade will soon give way to light-filled residences — each floor an entire home, each window a statement of craftsmanship and permanence.