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Dave Portnoy Of Barstool Sports Acquires Waterfront Mansion In Islamorada For $27.8M

Property Image
SOLD
$27,800,000
Dave Portnoy
Leslie Leopold
+ 1

Florida

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Single Family10,200 SF
Sold
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SOLD

Dave Portnoy Of Barstool Sports Acquires Waterfront Mansion In Islamorada For $27.8M

76180 Overseas Highway

See Similar Deals
Single Family10,200 SF
Sold
Dave Portnoy
Leslie Leopold
+ 1
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Summary

FLORIDA
Asset Type:Single Family
Price Per Square Foot:$2725
Total Square Footage:10200 SF
Transaction Type:Sale

The property asset involved in this transaction is a single-family home located at 76180 Overseas Highway in Islamorada, which spans 1.7 acres. The residence offers a substantial area of 10,200 square feet and has been sold for a total of $27,800,000. This sale represents the most expensive home sale in the Florida Keys to date.

Summary of transaction details:

  • Property Type: Single Family
  • Transaction Amount: $27,800,000
  • Address: 76180 Overseas Highway
  • Market: Islamorada
  • Acres: 1.7
  • Square Footage: 10,200
  • Price Per Square Foot: $2,725
  • Buyer: Dave Portnoy - Barstool Sports
  • Seller: Tom & Caryl Donatucci
  • Buyer's Representative: Angel Nicolas - Serhant
  • Seller's Representatives: Leslie Leopold & Cheri Tindall - Ocean Sotheby’s International Realty

This transaction was facilitated by key representatives from notable companies, with Angel Nicolas from Serhant representing the buyer, Dave Portnoy, while the seller was represented by Leslie Leopold and Cheri Tindall from Ocean Sotheby’s International Realty. The successful closing of this sale underscores the involvement of prominent individuals in the real estate market.

Players

Angel Nicolas
18 deals$158M volume(305) 336-0916
BROKER

Leslie Leopold
Sotheby's International Realty
1 deal$27.8M volume(305) 942-0215
BROKER

Cheri Tindall
Sotheby's International Realty
1 deal$27.8M volume(305) 664-7661
BROKER

Serhant
BROKERAGE


Dave Portnoy
7 deals$93.5M volume
BUYER

Details

SOLD
IMAGE: Angel Nicolas, Leslie Leopold, Dave Portnoy, Cheri Tindall & Miss Peaches the Dog DATE: 10/07/2025 ADDRESS: 76180 Overseas Highway MARKET: Islamorada ASSET TYPE: Single Family ~ ACRES: 1.7 BUYER: Dave Portnoy (@StoolPresidente) - Barstool Sports SELLER: Tom & Caryl Donatucci BUYER'S REP: Angel Nicolas (@Angel_Nicolas) - Serhant (@Serhant) SELLER'S REP: Leslie Leopold & Cheri Tindall - Ocean Sotheby’s International Realty SALE PRICE: $27,800,000 SF: 10,200 ~ PPSF: $2,725 NOTE: Barstool Sports founder Dave Portnoy bought a waterfront mansion in Islamorada for $27.8M, marking the most expensive home sale ever in the Florida Keys. The 1.7-acre property at 76180 Overseas Highway, sold by Tom and Caryl Donatucci, spans over 10,200 SF and was listed by Ocean Sotheby’s Leslie Leopold and Cheri Tindall, with Serhant’s Angel Nicolas representing Portnoy.

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