The luxury real estate landscape is undergoing a structural transformation. In the past 18 months, verified transactions totaling over $1 billion signal a strategic repositioning among America’s wealthiest individuals. The pattern is clear: capital is moving, tax domiciles are changing, and a transatlantic corridor between the U.S. and Italy is gaining institutional momentum.

The Numbers Behind the Movement

March 2025 marked New York City’s most expensive residential sale of the year: media mogul Byron Allen offloaded his full-floor condominium at 220 Central Park South for $82.5 million. The transaction was notable not just for its size, but for its speed. Allen had purchased the 6,600-square-foot residence less than two years earlier for $75 million, netting a $7.5 million profit in barely 24 months.
This wasn’t an isolated event. The same building has become a barometer for ultra-luxury sentiment. In 2019, hedge fund manager Ken Griffin set a U.S. record with a $238 million penthouse purchase there. In 2021 and 2022, Alibaba co-founder Joe Tsai acquired units totaling nearly $350 million. The building isn’t just expensive. It’s a statement of arrival.
But here’s where the story turns interesting. While some are buying in Manhattan, others are exiting entirely. Griffin himself has orchestrated one of the most significant corporate relocations in recent history, moving Citadel’s headquarters from Chicago to Miami. The hedge fund titan has assembled over $670 million in Miami real estate, including a 4.2-acre Brickell site where construction begins in 2025 on a $1 billion, 54-story supertall designed by Foster + Partners.

Florida’s Calculated Appeal

The migration to Florida isn’t coincidental. It’s mathematical. New York’s combined state and city income tax approaches 15% for high earners. Florida has zero state income tax, zero capital gains tax, and zero estate tax. For someone earning $50 million annually, that’s $7.5 million saved every year simply by changing their primary residence.
Jeff Bezos made this calculation explicit when he announced his move from Seattle to Miami in November 2023. Between August 2023 and April 2024, the Amazon founder spent $237 million acquiring three adjacent properties on Indian Creek Island, Miami’s ultra-exclusive “Billionaire Bunker.” The neighborhood, limited to just 41 homes on a 300-acre man-made island, now houses Tom Brady, Ivanka Trump, Jared Kushner, and Carl Icahn.
Bezos isn’t planning to live in all three mansions. According to reports, he intends to demolish two of them and construct a single mega-estate, using the third as temporary housing during construction. The message is unambiguous: this isn’t a vacation home strategy. It’s a complete relocation of primary residence and tax domicile.

The Italian Alternative

While Florida captures domestic migration, Italy has emerged as the unexpected beneficiary of American capital seeking international diversification. According to FIAIP, Italy’s professional real estate federation, Americans now represent 30% of all foreign property inquiries in Italy, a figure that increased 2.8% in 2024 compared to 2023.
The appeal is multifaceted. Exchange rates have made Italian property comparatively affordable. What cost €5 million in 2021 might still be €5 million today, but at current exchange rates, that translates to meaningful dollar savings for U.S. buyers. More significantly, Italy introduced favorable tax treatment for new residents in 2019, capping annual income tax at €100,000 for qualifying individuals who establish Italian tax residency.
The lifestyle arbitrage is equally compelling. A $3 million budget in Manhattan yields approximately 1,100 square feet in a competitive neighborhood. The same $3 million in Tuscany, Umbria, or Piedmont purchases a restored historic villa with multiple bedrooms, land, and vineyard views. Italian property prices rose just 2.1% in 2024, according to Idealista, making Italy one of the slowest-appreciating markets in the European Union. For buyers, that means stability rather than speculation.
Lake Como remains the most sought-after destination at 4.8% of requests, followed by Salento and Lunigiana. Americans aren’t just buying vacation homes. They’re exploring structures that allow part-time residency while maintaining U.S. business interests.

What This Means for Investors

These aren’t lifestyle decisions masquerading as investments. They’re tax-optimized portfolio restructurings executed by individuals with access to elite advisors. The playbook has become consistent: establish primary residence in a no-tax state, maintain a presence in New York for business and cultural access, and acquire strategic European property in markets with favorable tax treaties and appreciation potential.
New York’s luxury market isn’t collapsing, but it is repricing. Properties that historically commanded 5-7% annual appreciation are now flat or slightly negative. Inventory has increased, days on market have extended, and sellers are accepting offers 10-15% below initial asking prices to achieve liquidity.
Meanwhile, select Italian markets are experiencing 8-12% annual growth, driven partly by American capital inflows and partly by limited supply in historic city centers where new construction is restricted. The dynamic creates opportunity for informed buyers who understand both regulatory environments.

The Complexity of Cross-Border Strategy

The regulatory frameworks couldn’t be more different. U.S. real estate transactions follow predictable patterns: title insurance, standardized contracts, mortgage financing widely available, and closings that typically occur within 30-60 days. Italy operates on a civil law system with different ownership structures, notary requirements that differ fundamentally from U.S. practice, inheritance laws that affect property transfer, and tax implications that require specialized knowledge.
For American buyers considering Italian property, the process involves obtaining a Codice Fiscale (Italian tax ID), understanding the compromesso (preliminary contract) that requires significant deposits before final closing, navigating VAT rates that range from 4-22% depending on property type and buyer status, and structuring ownership in ways that optimize both U.S. and Italian tax obligations.
For Italian investors evaluating U.S. opportunities, challenges include understanding FIRPTA withholding requirements, navigating state-by-state tax variations, structuring ownership through appropriate entities, and managing currency risk on dollar-denominated assets.
The transaction complexity explains why cross-border real estate remains the domain of sophisticated investors rather than retail buyers. It also explains why having advisors who genuinely understand both markets, not just one, has become essential rather than optional.

Looking Ahead

The pattern established over the past 18 months suggests durability rather than anomaly. Tax policy in high-tax states shows no signs of reversal. Remote work has permanently altered the equation of where high earners need to be physically present. And the euro-dollar exchange rate continues to make European property attractive for dollar-based buyers.
For investors, the implication is clear: global portfolio construction now means literal geographic diversification, not just asset class diversification. The wealthy aren’t abandoning global cities. They’re becoming more intentional about where they establish tax domicile, where they park capital, and how they structure ownership to maximize efficiency across jurisdictions.
The Italy-U.S. corridor has moved from novelty to established strategy. Those who understand how to navigate it effectively, with expertise on both sides of the Atlantic, are positioned to capitalize on a trend that appears structural rather than cyclical.

Columbus International Real Estate operates at this precise intersection. Headquartered at Rockefeller Center in New York, with strategic offices in Miami, Milan, and Florence, the firm specializes in the Italy-U.S. corridor that has become central to high-net-worth portfolio strategy. For Italian investors seeking access to American markets or U.S. buyers exploring European opportunities, Columbus International provides comprehensive guidance across both regulatory environments. More than a transaction facilitator, the firm serves as a market observatory, connecting luxury developers with international clientele who increasingly think in terms of global portfolios rather than single-market holdings. Understanding tax treaties, ownership structures, and market dynamics on both continents isn’t just valuable – it’s essential.

Contact Us: info@columbusintl.com