What prompted Josh Flagg to sell his $10 million Miami estate on Billionaires' Row? Reason explained

Josh Flagg has put his $10 million Miami estate on the market, and many people want to know why. The home sits on North Bay Road, also called “Billionaires’ Row,” one of the most famous and expensive streets in Miami Beach. The area is known for its luxury homes and well-known residents.

Flagg’s estate is a fully rebuilt Mediterranean-style home. It has four bedrooms, five bathrooms, a detached pool house, and upgraded security. The renovation was completed with designer Gary Eisner from BuiltIN Studio. Flagg says the home is almost finished and will be ready for a buyer in about sixty days.

Even with all of its features, Flagg says there is a clear reason for selling now. His decision is tied to recent political changes that he believes will push more wealthy buyers toward Miami.

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Political change and rising demand

Josh Flagg explained that the timing of the listing was intentional. He said he put the Miami home up for sale right after New York elected a new governor.

As he said, “The minute New York elected Mandahmi, I called my broker Jordan Karp. I didn't even wait for the acceptance speech.”

Flagg believes this political shift may lead many wealthy New Yorkers to move or invest in Florida.

Flagg says New Yorkers tend to react fast when there is uncertainty. He described how quickly things change, saying “One politician says they'll ‘make the rich pay,’ and planes at Teterboro start fueling up faster than the Bergdorf sale.”

He was referring to the fact that many wealthy people relocate before any new policy is implemented.

He also joked about how fast some people claim they left the city.

Flagg said, “A week later, everyone from Manhattan claims they ‘escaped New York,’ like they tunneled out of Shawshank with a Birkin.”

His comment reflects his view on how quickly buyers react.

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Josh Flagg’s strategic business move

This sale is also a business decision for Josh Flagg. The Miami home is owned by Flagg Family Capital, his family’s private real-estate investment group. It is also partnered with Carolwood LP. Listing the home now fits into their long-term investment plans.

Flagg shared that he has expanded his real-estate investments in other places. He recently bought a property in East Hampton and a commercial building in downtown Manhattan.

He said, “I love New York — it’s home half the month.”

Even though he expects many wealthy people to leave New York, he still sees value in owning there.

Flagg also said he is not fully leaving Miami. He even revealed that he has never spent a night in the Miami home.

“I can’t say I’m leaving Miami … I’ve never even spent a night there,” he said.

This indicates that the sale is a business decision rather than a personal one.

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