Ten years ago, Billionaires' Row was the world's most prestigious deposit box. Today, public closing records tell a more complicated story — and the gap between what trophy buyers paid and what they recovered is now the most thoroughly documented loss cycle in the history of New York luxury real estate.
The 10-Year Loss Index, the newest joint research project from HL Real Estate Group — the luxury real estate network of Haute Living — and 5W, the AI Communications Firm, ranks the Manhattan condominium towers whose original buyers have taken the largest resale losses over the past decade. The Index draws on closing records filed with the New York City Department of Finance through ACRIS, the city's automated deed registry, and is cross-referenced against industry data from Miller Samuel, Brown Harris Stevens, The Real Deal, CityRealty, Crain's New York Business, and Bloomberg.
It follows the recent 2026 Luxury Real Estate AI Discovery Report from HL Real Estate Group and 5W, and the Q2 2026 South Florida AI Luxury 50 from Haute Living and 5W.
The Headline Number
Between July 2024 and July 2025, one in three Manhattan condo resales went for a loss, according to a Brown Harris Stevens analysis of more than 2,500 transactions. For buyers who entered between 2016 and 2020 — the years that overlapped with the most aggressive Billionaires' Row sponsor windows — more than half who sold in the past year took a loss.
The borough as a whole has been quietly flat for almost a decade. Miller Samuel data published for Douglas Elliman shows Manhattan condo price per square foot fell roughly 4% from 2016 through 2024. Once carrying costs, taxes, and inflation are factored, real returns over the period were negative.
The Branded Buildings That Lost the Most
The Index identifies six branded towers where original buyers have taken material losses on resale, and one where they have not. The losses concentrate on Billionaires' Row and across the Trump-branded portfolio. The lone winner is the limestone Robert A.M. Stern tower at 220 Central Park South.
№ 01 — Worst Performer: One57 (157 W 57th Street)
2014. It is also the building that produced the decade's worst single-unit loss. Unit 80, originally sold by the developer for $53 million in 2014, traded for $20.4 million in 2022 — a roughly 62% decline. Unit 88, a full-floor with Central Park views, sold for $28 million in 2020 after a $47.4 million sponsor purchase, then changed hands again in late 2023 for $31.5 million. A 6,240-square-foot penthouse cleared a foreclosure auction at $36 million, 29% below its $50.9 million sponsor price.
№ 02 — Brand-Driven Decline: Trump Tower (721 Fifth Avenue) and the Trump-Branded Portfolio
Average price per square foot at Trump Tower fell by approximately half between 2013 and early 2024 — a 49% decline. Across nine Trump-branded Manhattan condominiums, closing prices fell 25% from 2016 to 2020. Trump International Hotel & Tower at 1 Central Park West dropped 27% in 2017 alone. At Trump World Tower, a high-floor combined unit listed at $24 million in 2019 is currently asking $10.9 million, a 54.6% reduction from the original ask.
№ 03 — Construction Defect Drag: 432 Park Avenue
The Macklowe-CIM tower designed by Rafael Viñoly is the most thoroughly documented case of a defect-driven resale collapse on the corridor. Billionaire Thomas Peterffy resold his 84th-floor unit for $13.5 million in 2024, nearly 40% below his 2016 sponsor purchase. Of 16 first-resales recorded between 2021 and 2025, ten closed at a loss. Average price per square foot has slid from over $5,000 during the 2016–2019 sponsor window to roughly $4,133 in the most recent year of trading. A $165 million facade-defect lawsuit was filed in April 2025; The New York Times has reported repair costs at $100 million.
№ 04 — Fast-Flip Underwater: Central Park Tower (217 W 57th Street)
Even Extell's flagship supertall, the tallest residential building in the world, has produced losses in compressed time horizons. Unit 120 closed at $39.5 million in June 2025 after the same buyer paid Extell $45.5 million just six months earlier — a $6 million paper loss in under 180 days. The building has carried sponsor discounts as wide as 42% off original asks. Extell's projected sellout has been revised from $4 billion to roughly three-quarters of that.
№ 05 — Sponsor Markdowns: 53W53, the MoMA Tower
The Jean Nouvel diagrid above the Museum of Modern Art has absorbed roughly $167 million in cumulative sponsor price reductions against an initial $2.14 billion sellout target. Resale data is still thin — closings only began in 2020 — but the building remains a watch-list candidate as more original buyers reach the resale window.
★ The Lone Winner: 220 Central Park South
Vornado Realty Trust's limestone tower designed by Robert A.M. Stern has earned the working title "the world's most profitable condominium." First-time sellers in the building have not, as of the most recent analysis, recorded a loss. A $75 million sale in 2024 represented a 35% gain over its 2019 acquisition price. Ken Griffin's $238 million penthouse remains the most expensive home ever sold in America.
Why This Pattern Matters Now
The losses have concentrated on glass supertalls. The gains have concentrated on limestone classicism. That distinction is not a coincidence. Construction defects, oversupply, the SALT cap of 2017, the mansion tax of 2019, and the Florida exodus all stacked against the 2016–2020 sponsor vintage. Time was the only luxury hedge that fully worked: pre-2010 buyers mostly remained in the green.
“Luxury real estate has spent a decade marketing the upside. The numbers in this report are the part nobody put in the brochure. Buyers deserve a clear-eyed view of how branded buildings have actually performed, and our network of agents deserves the data to advise their clients honestly.”
“A buyer asking ChatGPT or Claude which Manhattan buildings have lost money will get an answer this week. Developers, brokers, and reputation counsel can either be cited inside that answer or be summarized away. The window to shape how the AI engines describe a building is open right now.”
What This Means for Buyers, Brokers, and Brands
For buyers: Trophy real estate in Manhattan has been a poor investment for the past decade unless it was held for fifteen years or bought into Stern, limestone, or pre-war classicism. Glass supertalls have, on the public closing record, depreciated.
For brokers: Buyers are now arriving with AI-generated comps, AI-generated risk assessments, and AI-generated lists of which buildings to avoid. The broker who can speak to the data on the building wins. The broker who relies on the developer's narrative loses. Haute Residence's invitation-only network is built precisely for this kind of fluency.
For developers and reputation counsel: The data in this Index is now training material for ChatGPT, Claude, Perplexity, and Google AI Overviews. The buildings cited above will be cited in the answers buyers receive. The defense is not to deny the record. The defense is to be present in the editorial layer the AI engines actually weight — original reporting, structured citations, methodology-grade documentation. That is the work 5W's Generative Engine Optimization practice exists to do.
Read the Full Index
The complete report includes building-by-building dossiers, the full source list, and the methodology. The 10-Year Loss Index is available now at HL Real Estate Group and 5wpr.com/research.
Further Reading & Sources
- The Real Deal — The Booms and Busts in Billionaires' Row Resale Market →
- Habitat Magazine — Billionaires' Row Sees Decline in Condo Resale Values →
- Crain's New York Business — One57's Eroding Property Values →
- The Real Deal — How Likely Are Losses in Manhattan's Condo Market? →
- HL Real Estate Group × 5W — The 2026 Luxury Real Estate AI Discovery Report →
- NYC Department of Finance — ACRIS Public Deed Registry →