Former HGTV Dream Home in Florida Keys Listed for $14.9 Million After Renovations

Nearly twenty years after its debut as the grand prize in HGTV's Dream Home contest, the 3,200-square-foot waterfront residence in the Florida Keys has re-entered the market with a $14.9 million asking price. The home, originally appraised at $2.2 million in 2008, was won by Stephanie and Tommy Dee of Iowa, who opted for the cash payout rather than moving in. Since then the property changed owners twice, first selling in 2009 and later being bought in 2021 for $8 million.

The latest proprietor has transformed the site into a private resort, adding a two-bedroom main house, a three-bedroom guesthouse, a one-bedroom media house, a 100-foot pool, cabana and panoramic views across three structures. The HGTV Dream Home giveaway, a staple since 1997, continues to award new homes each year; the 2026 prize went to Atlanta resident Eileen Reimer for a lake-front house in North Carolina. The listing highlights the evolution of a once-public giveaway property into a high-end real-estate asset.