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Reading: Dave Portnoy breaks Florida Keys gross sales document with $27.8M waterfront mansion
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The Wall Street Publication > Blog > Lifestyle > Dave Portnoy breaks Florida Keys gross sales document with $27.8M waterfront mansion
Lifestyle

Dave Portnoy breaks Florida Keys gross sales document with $27.8M waterfront mansion

Editorial Board Published October 8, 2025
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Dave Portnoy breaks Florida Keys gross sales document with .8M waterfront mansion
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Barstool founder Dave Portnoy discusses his new take care of FOX Sports activities on ‘Varney & Co.

Barstool Sports activities founder Dave Portnoy snapped up one other Florida mansion so as to add to his rising multimillion-dollar actual property portfolio. 

The waterfront property boasted an inventory worth of $31.2 million in June. Portnoy secured it for $27.75 million, a record-breaking deal for Islamorada, in line with The Wall Road Journal. Islamorada is a village of islands positioned within the Florida Keys.

Village of Islamorada’s official web site described the realm as a tourism-oriented group an hour south of Miami consisting of 4 islands spanning 18 linear miles with a land space of roughly 3,900 acres. 

BARSTOOL’S DAVE PORTNOY OFFERS INVESTING ADVICE, BUT REVEALS ONE BIG CAVEAT

The upscale, small city options a number of eating places, quaint outlets and galleries, in line with the web site. It’s also generally known as the “Sport Fishing Capital of the World” and is house to roughly 7,107 individuals, in line with 2023 Census knowledge. 

PENN-ESPN DEAL ALLOWS BARSTOOL SPORTS FOUNDER DAVE PORTNOY TO BUY BACK COMPANY FOR $1

FOX Enterprise reached out to Leslie Leopold and Cheri Tindall of Ocean Sotheby’s Worldwide Realty, who marketed the property, for remark. 

A bed room inside Barstool founder Dave Portnoy’s not too long ago bought Florida Keys mansion.

This house is the newest that Portnoy is including to his $95 million actual property portfolio that spans New York, Massachusetts and Florida, in line with a number of experiences.

DAVE PORTNOY’S $42 MILLION NANTUCKET HOME BREAKS RECORD

In 2023, the Barstool Sports activities founder acquired a Nantucket house in a transaction that broke not less than two sale information. 

Portnoy’s house, bought for $42 million, was constructed on a pair of land parcels totaling 1.2 acres, and sits close to the seashore in Monomoy, a part of Massachusetts’ Nantucket island, in line with The Wall Road Journal. 

Kitchen in Dave Portnoy's Florida Keys mansion.

A kitchen inside Barstool founder Dave Portnoy’s not too long ago bought Florida Keys mansion. (1 OAK Studios)

Portnoy is greatest recognized for Barstool Sports activities, a digital media firm that mixes sports activities, popular culture, comedy and viral content material, which he based greater than twenty years in the past. In August 2023, the Massachusetts-native paid $1 to repurchase it, having beforehand bought it to PENN Leisure for some $500 million, FOX Enterprise reported. 

GET FOX BUSINESS ON THE GO BY CLICKING HERE

Except for Barstool, Portnoy has additionally created a high-demand video sequence, “One Bite Pizza Reviews.”

TAGGED:27.8MBreaksDaveFloridakeysmansionPortnoyrecordsalesWaterfront
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