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76180 Overseas Highway

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

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

76180 Overseas Highway

$27,800,000

$2,725/SF

Building Size

10,200 SF

Asset Type

Single Family

Closing

Oct 7, 2025

AI

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

Serhant

Broker

$158M

vol

18 deals

Broker
Serhant
SerhantBrokerage
Dave Portnoy

Dave Portnoy

Barstool Sports

Buyer

$93.5M

vol

7 deals

Buyer

Islamorada Single Family Market Snapshot

Boundary boundary · Single Family · Sale transactions

Loading comparables…

Purchase Price

Annual NOI

Loan Amount

Interest Rate (%)

Loan Term (yrs)

Down Payment (%)

Cap Rate

0.57%

Cash-on-Cash

-0.16%

Monthly Payment

$14,164

Annual Debt Svc

$169,964

Annual Cash Flow

$-11,334

DSCR

0.93