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David Portnoy Buys $27.75M Florida Estate, Expands Portfolio

10/25/2025

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Summary

Story summary

David Portnoy, founder of Barstool Sports, purchased a bayfront estate in Islamorada, Florida for $27.75 million, spanning 1.65 acres with two residences totaling over 10,000 square feet, the highest Florida Keys sale outside Ocean Reef.
His luxury real estate portfolio is now valued at $95 million.
He remains active in sports media and recently attended the Indiana versus UCLA football game, where excitement among fans was palpable.

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Story summary

David Portnoy, founder of Barstool Sports, purchased a bayfront estate in Islamorada, Florida for $27.75 million, spanning 1.65 acres with two residences totaling over 10,000 square feet, the highest Florida Keys sale outside Ocean Reef.
His luxury real estate portfolio is now valued at $95 million.
He remains active in sports media and recently attended the Indiana versus UCLA football game, where excitement among fans was palpable.