Miami is joked of as New York City’s sixth borough, but the relationship between the two cities’ real estate industries is serious.
The flight path between New York City and Miami International is one of the busiest domestic routes in the country, and some of Manhattan’s biggest developers have been flying south to invest billions in projects throughout the tri-county region. While the bond has existed for decades, pandemic market shifts deepened the connection between the already intertwined cities.
This dynamic is on full display in The Real Deal’s South Florida and New York Top 100 lists, which feature New Yorkers with deep pipelines in Florida.
Here’s a look at some of the TRD 100’s snowbirds reshaping the South Florida skyline.
Harry Macklowe
Harry Macklowe, the 90-year-old Manhattan real estate titan known for high highs and low lows, threw his hat in the Miami ring in recent years. He has partnered with the Pérez family’s Related Group on a two-tower, 43-story, 364-unit luxury condo project in North Bay Village. It is rumored that the Arquitectonica-designed project will also bear the Ritz-Carlton brand.
In 2022, he paid $31.9 million for a site near the Dadeland Mall, where he planned a 770-unit residential project. After Fortress Investment Group initiated a foreclosure on the site in 2024, Macklowe sold the land to the Pérezes for $20 million.
Steve Ross
Fresh off the completion of Hudson Yards in New York City, the billionaire magnate Steve Ross turned his attention to a gargantuan development effort in West Palm Beach. In 2024, he spun the South Florida portfolio of his Related Companies off and formed Related Ross to focus almost exclusively on his myriad projects in the Palm Beach County city. They include more than 3.8 million square feet of offices, retail and restaurants, four condo projects and a proposed 400-key hotel.
It’s a sort of homecoming for Ross, who grew up in Miami Beach and has owned his historic oceanfront Palm Beach estate, known as the Reef, since 2007. He frequently cites his belief in West Palm Beach’s future as a global hub of innovation and commerce and has been an instrumental player in luring institutions like Vanderbilt University and Cleveland Clinic to the city.
Michael Stern
Michael Stern, the CEO of his JDS Development Group, is perhaps best known for super-tall residential projects in New York City, including the Steinway Tower residential supertall at 111 West 57th Street, The Copper rental apartment skyscrapers and the Brooklyn Tower.
Stern is also behind some of the splashiest towers planned in Miami, including the Dolce & Gabbana-branded condo-hotel tower slated for 888 Brickell Avenue which has about $350 million in pre-sales.
But Stern, who is known to clash with investors and lenders, is facing some bumps with his Miami pipeline.
In a scathing complaint filed in December, Italian investor Gianluca Vacchi sued Stern, alleging “deliberated and calculated fraud” concerning Vacchi’s investment in a planned redevelopment at the Casablanca condo-hotel in North Beach. Vacchi is also an investor in Stern’s planned Mercedes-Benz Places, a planned 800-unit, two-tower development in Miami now facing foreclosure.
Miki Naftali
Miki Naftali, a longtime titan of luxury development in New York, has set his sights on the often-overlooked downtowns of Miami and Fort Lauderdale for his pipeline of South Florida projects. In 2022, he partnered with Cara Real Estate Management to drop $40.5 million on a Miami Worldcenter site where he plans a two-tower, 936-unit rental development. He also paid $20 million for a Fort Lauderdale site where he is planning a 251-unit Viceroy-branded condominium.
“What is missing here is quality,” Naftali told TRD last year in an interview about the growing condo pipeline in Fort Lauderdale.
The Eichners
Ian Bruce Eichner and his daughter Alexandra Eichner are another example of New Yorkers building in South Florida. While the Eichner’s Continuum Company made its name building projects like New York’s Madison Square Park Tower, One Broadway Place and Manhattan Club, South Florida is now its most active market. Their Miami-Dade County pipeline includes the multi-phased La Baia in Bay Harbor Islands and a condo and hotel slated for North Bay Village. In February, the father-daughter duo launched sales for the planned 12000 Sport & Wellness Waterfront Residences in North Miami after completing a $48.5 million bulk buyout in the fall.
