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
Islamorada Single Family Market Snapshot
Boundary boundary · Single Family · Sale transactions
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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