![Celebrities [Portnoy], [Anthony], [Sweeney] in luxury real estate.](https://floridarealestatewire.com/wp-content/uploads/2026/01/3e5f88f9thumbnail.jpeg "Celebrity Real Estate Buzz: Portnoy, Anthony, and Sweeney Make Major Moves")
The luxury real estate market continues to attract high-profile individuals, with recent notable transactions involving media mogul Dave Portnoy, music superstar Marc Anthony, and actress Sydney Sweeney. These deals highlight a trend of celebrities investing in prime waterfront properties, from the exclusive Florida Keys to the vibrant heart of Miami.
Key Takeaways
- Dave Portnoy acquired a sprawling Florida Keys estate for $27.75 million.
- Marc Anthony experienced a significant loss on the sale of his Miami luxury condo.
- Sydney Sweeney purchased a lavish Florida Keys mansion for $13.5 million.
Dave Portnoy’s Florida Keys Compound
Barstool Sports founder Dave Portnoy has expanded his real estate portfolio with the purchase of a $27.75 million waterfront compound in Islamorada, Florida Keys. The expansive property spans 1.65 acres and boasts eight bedrooms and ten bathrooms across 10,228 square feet. Features include 150 feet of private waterfront with dockage and beach access, a main house with high-end amenities like a built-in coffee system and wine cellar, and a separate guest house with its own pool. The outdoor kitchen is equipped with a pizza oven, a nod to Portnoy’s famous "one-bite" reviews.
Marc Anthony’s Miami Condo Sale
Latin music icon Marc Anthony has reportedly sold his luxury condominium at One Thousand Museum Tower in downtown Miami for $8.6 million. This sale represents a loss of nearly $2.4 million, as Anthony originally purchased the 8,400-square-foot, five-bedroom residence for $11 million in 2011. The condo offers panoramic views of Biscayne Bay and access to the building’s five-star amenities, including a helipad. While this particular transaction was not profitable, Anthony has seen success in previous South Florida real estate dealings.
Sydney Sweeney’s Coastal Oasis
Actress Sydney Sweeney has invested in a stunning $13.5 million mansion in the Florida Keys, located approximately 30 minutes from Key West. The 7,720 sq. ft. estate, purchased for $4.5 million below its original listing price, offers a blend of modern luxury and island charm. The property features water on two sides, a 100-foot seawall for private docking, and resort-style amenities such as an infinity pool with a swim-up bar, a wine room, and a private boat launch. The estate is divided into a main residence and a guesthouse, connected by a breezeway, creating a private courtyard feel.
Sources
- Dave Portnoy drops $28M on waterfront Florida mansion, Boston.com.
- Marc Anthony Loses Millions in Miami Condo Sale | Luxury Toys, IslanderNews.com.
- From Hollywood to the Keys: Sydney Sweeney’s $13.5M Mansion Is Pure Coastal Luxury, hauteresidence.com.