Donald Trump Jr.’s New Relationship Complicates $15M Mansion Split with Kimberly Guilfoyle

Donald Trump Jr. and Kimberly Guilfoyle’s breakup has gone from personal to political — and now, potentially legal — as the fate of their sprawling $15 million Florida mansion hangs in the balance amid Don Jr.’s budding romance and Guilfoyle’s likely move abroad.

Kimberly Guilfoyle, 55, and Donald Trump Jr.'s, 46, $15million mansion they purchased in 2021 will be a battleground for the recently split couple as their ideas of what to do with it differ

The 11,300-square-foot Admiral’s Cove estate, located in Jupiter, Florida, was purchased in 2021 by the couple for $9.7 million shortly after Trump Jr.’s father left the White House. Now valued at over $15 million, the waterfront property was a symbol of the couple’s high-profile union. Today, it may become a battleground in their very public unraveling.

Adding fuel to the fire is Don Jr.’s new relationship with Florida socialite Bettina Anderson, 38, which he took public in December after the pair were seen holding hands following a birthday dinner at Buccan, a chic Palm Beach restaurant. According to reports, the two have since been spending time together at Anderson’s modest West Palm Beach home — a far cry from the Jupiter mansion, both in size and security.

The mansion is a 11,300 square-foot six-bed, 11-bath home that the former couple bought for $9.7million. The Admiral Cove estate is located in Jupiter, Florida

“She’s a better fit for him,” one Trump insider, noting her classic style and polished image. “He’s bewitched by Bettina — her looks, her smarts, her pedigree.”

The high-profile nature of the new relationship, contrasted with Kimberly’s sudden diplomatic pivot, has only intensified public fascination. Guilfoyle, 55, is expected to soon be confirmed as U.S. ambassador to Greece — a nomination many insiders believe was orchestrated not only to reward her long-time loyalty to the Trump family, but also to create distance following the couple’s quiet split.

The former couple was originally drawn to the mansion because of its 1.2-acre lot that was larger than other homes in the Admirals Cove area for Don Jr's five children

“She was blindsided by the timing of Don Jr.’s new relationship going public”, “but being stationed in Athens gives her a clean break and a powerful new role.”

Yet, the physical and legal distance brings fresh complications. The Jupiter estate was purchased as tenants in common, giving both parties the ability to sell or transfer their ownership stake independently. If Guilfoyle relocates full-time to Greece and Don Jr. wishes to keep or repurpose the home — potentially even move in with Anderson — legal wrangling could follow.

“I doubt Kimberly is thrilled about the idea of Don Jr. bringing his new girlfriend into the home she invested so much effort into,” a source close to the matter revealed. “Honestly, I’m not sure Bettina would want to move into a house where Don lived with Kimberly.”

The Admiral’s Cove property is one of the largest in the exclusive 188-home gated community. With six bedrooms, 11 bathrooms, and a rare 1.2-acre lot, the mansion offered ample room for Don Jr.’s five children, who live nearby. That, reportedly, was one of the key attractions when the couple purchased it.

But with Don Jr. now staying at Bettina’s significantly smaller residence and Kimberly preparing for an international posting, the property may be left in limbo.

Though neither party has made a public legal move regarding the estate, the writing may be on the wall. Real estate experts suggest that high-value jointly owned homes — especially those entangled in emotional and public breakups — often become flashpoints for litigation or pressured sales.

“It’s a trophy property,” a local real estate agent familiar with the area said. “But it’s also a symbol of a relationship that’s no longer intact. Those types of homes often get offloaded quietly.”

Guilfoyle, a former Fox News personality and legal analyst, is fully leaning into her next chapter. In a statement on social media, she expressed her enthusiasm for the ambassadorship and emphasized the historical bond between the U.S. and Greece.

“It was the democratic values born in Greece that helped shape the founding of America,” she wrote. “Now, we have an opportunity to honor that history by bringing better days here at home and abroad.”

Former President Donald Trump praised her nomination, citing her “extensive experience and leadership in law, media, and politics.” Don Jr. echoed the sentiment, tweeting: “I am so proud of Kimberly. She will be an amazing leader for America First.”

Despite the positive public gestures, insiders suggest the couple’s private breakup was far less cordial. Sources say Kimberly had hoped to keep up appearances until the end of the year but was “caught off guard” when Don Jr. and Anderson began publicly “parading their love.”

Anderson, meanwhile, has posted subtle social media nods to her new relationship, including a floral arrangement tagged discreetly with @donaldtrumpjr. Friends describe her as smart, well-connected, and eager to “step into a new public-facing chapter” with Trump Jr.

Whether that chapter includes the Jupiter mansion remains unclear — but one thing is certain: the luxurious home that once symbolized Don Jr. and Kimberly’s future is now the setting for a very uncertain present.

As Guilfoyle prepares to cross the Atlantic and Trump Jr.’s new relationship gains traction back home, fans — and lawyers — will be watching closely to see what happens next.