Islamorada Mansion Returns With $1.75M Price Hike

A waterfront estate in Islamorada, Florida, has returned to the market with a $1.75 million price increase, now listed at $13.75 million. The property previously sold in February of this year for $12 million, having been listed the month prior for $12.95 million. Listing agent Lisa Swanson of The Agency Florida Keys attributes the price hike to aesthetic improvements made by the seller and a surge in interest in the community, partly influenced by the purchase of a nearby estate by Barstool Sports founder Dave Portnoy.

Portnoy, aged 49, acquired a significant Islamorada estate for $27.8 million in October 2025, setting a record for the most expensive property sale in the area at that time. Swanson stated that Portnoy's purchase has "definitely helped put Islamorada on the market," leading to increased buyer interest, particularly for luxury, turnkey properties. Since Portnoy's transaction, sales in Islamorada have reportedly increased by approximately 20%.

Swanson further noted that the presence of "trophy properties" in the area, combined with the mention of Dave Portnoy's home, attracts more attention from both potential buyers and sellers. Realtor.com® data indicates a significant increase in market activity in Islamorada between December 2024 and December 2025, suggesting a growing demand for high-value coastal real estate in the enclave.