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Dave Portnoy's $27.75M Mansion Sets Islamorada Record

10/9/2025

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Summary

Story summary

Dave Portnoy buys a Florida mansion for $27.75 million, a record in Islamorada.
Islamorada spans 18 miles with a 2023 population of 7,107.
His real estate portfolio totals $95 million across New York, Massachusetts, and Florida.
In 2023, he bought a Nantucket home for $42 million, breaking records.
Portnoy repurchased Barstool Sports for $1 after selling it for $500 million.

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Story summary

Dave Portnoy buys a Florida mansion for $27.75 million, a record in Islamorada.
Islamorada spans 18 miles with a 2023 population of 7,107.
His real estate portfolio totals $95 million across New York, Massachusetts, and Florida.
In 2023, he bought a Nantucket home for $42 million, breaking records.
Portnoy repurchased Barstool Sports for $1 after selling it for $500 million.