Just recently President Donald Trump publicly announced his eldest son’s engagement at the White House in December 2025, roughly a year after Trump Jr.’s relationship with Guilfoyle ended and now the pair is making some important decisions.
Donald Trump Jr. and his former fiancée Kimberly Guilfoyle are privately offering their shared Florida residence for sale, according to reporting by Gimme Shelter.
The outlet reports that the Jupiter property, located within the gated waterfront community of Admirals Cove, is being marketed as a “whisper” listing with an asking price of approximately $30 million.
The former couple purchased the home in 2021 for $9.7 million, shortly after President Donald Trump concluded his first term in office. Trump Jr. and Guilfoyle were together from 2018 until 2024.
A waterfront property in an exclusive enclave
The two-story residence spans 11,300 square feet and includes six bedrooms and 11 bathrooms. The property features a pool and a private dock along the Intracoastal Waterway capable of accommodating an 85-foot boat.
Inside, the home offers an elevator, a wine room and a chef’s kitchen. The estate sits on 1.2 acres, a parcel described as larger than most within the upscale community.
The property is also located about a 30-minute drive from Mar-a-Lago and is situated even closer to Trump National Golf Club.
A source told Gimme Shelter, “It’s a beautiful house and it is finally ready to sell. There’s a ton of interest.” The same source noted that there had been some back and forth between the former couple regarding the potential sale.
Life changes following the breakup
Since their separation, both have moved forward personally and professionally.
Trump Jr. was first linked to Anderson after the two were photographed holding hands in Florida, around the same time his relationship with Guilfoyle was coming to an end.
More recently, sources have suggested that he sees parallels between Anderson and First Lady Melania Trump, noting Anderson’s modeling background and social ties in Palm Beach.
Trump Jr., a father of five with ex-wife Vanessa Trump, is now engaged to Palm Beach socialite Bettina Anderson. Guilfoyle, a former prosecutor and Fox News personality, is currently serving as ambassador to Greece.
She is residing in what has been described as a “sprawling” Mediterranean-style official residence in Athens and recently appeared on the cover of Vogue Greece.
In an interview with The New York Times last month, Guilfoyle said of her former partner, “I’m happy for Don. I wish him, of course, all the best.”
It remains unclear whether the Jupiter home includes a dedicated gun room. Gimme Shelter previously reported that Trump Jr., an avid hunter, had specifically requested such a room for his Hamptons property to display and store his collection.
For now, the Florida estate stands as a high-profile property entering the market quietly, as interest reportedly builds behind the scenes.
