Katy Perry is famous for her music, her adventurous fashion sense, and her long run as a judge on American Idol. But lately she's been in the public eye for her unlucky real estate holdings. Between a deal with the Roman Catholic Archdiocese gone wrong and a years-long battle over a Montecito property that allegedly involves Chris Pratt and Katherine Schwarzenegger, there's been plenty of chatter and confusion. After months of negotiations, the prolonged legal dispute over the Montecito property is coming to a close—and there’s finally a settlement on the table for the pop star. For all those wondering how we got there, here’s what you need to know.
The Montecito misfire
The most recent of Perry’s public real estate battles surrounds the $15 million purchase of an estate in Montecito, California, a small town near Santa Barbara preferred by celebrities like Gwyneth Paltrow, Oprah, and Ariana Grande. In the summer of 2020, Perry and her then-fiancé Orlando Bloom were looking for a home in the area for their family, as she was pregnant with their daughter. Perry’s business manager Bernie Gudvi presented homeowner Carl Westcott with a written offer for his home in July 2020. The home was not on the market at the time, and Westcott had been out of the hospital for four days following back surgery and was allegedly on painkillers when he signed, leading Westcott and his lawyers to later contest the validity of the deal. The homeowner and his lawyers attempted to rescind the deal, and Westcott filed a suit against Gudvi in August of 2020.
On November 8, 2023—over three years later—the court ruled in favor of Perry. “Westcott presented no persuasive evidence that he lacked capacity to enter into a real estate contract,” reads the court’s decision, per People. According to The Daily Beast, Judge Joseph Lipner said that the medical expert’s testimony did not support Westcott’s claims. Compounding the questionable nature of Westcott’s rescinding was his real estate agent’s claim that he in fact had a backup offer on the home in place from Maria Shriver.
The legal battle over the Montecito home continued. After a verdict in the singer’s favor validated her ownership of the home—followed by a transfer of the property’s deed to her LLC in May 2024—Perry made a court appearance in August, initiating the second phase of the trial. Perry testified about lost rental income and repairs; the singer’s team argued that she is entitled to $3.5 million in damages for lost fair-market value from when the deal closed in September 2020 to when Perry secured the keys to the property in March 2024.
Law Commentary reports that Westcott argued that the house could not have been in disrepair if Perry had rented it out—which she allegedly did to tenants Chris Pratt and his wife, Katherine Schwarzenegger. Perry’s team reportedly countered that she was not seeking reimbursement for completed repairs, but rather, for compensation on restorations to return the home to the original condition it was purchased in, per the agreement. Perry’s team claimed they are owed $2.2 million for the repairs. Alleged damages include flooding and cracking in the building’s foundation, among other issues cited throughout the property. On top of that, Perry’s team is said to be seeking $3 million in legal fees. Westcott’s legal team has denied that the home was damaged from 2020 to 2024.
Additionally, Westcott filed to depose Perry’s former fiancé, Orlando Bloom. The entrepreneur’s legal team wanted to question Bloom about repairs to the home and whether the actor ever lived in the house with Perry. Us Weekly reported that Perry’s team asked the judge to shut down the subpoenas issued to Bloom, claiming that the requests were untimely; coming amid the news of Perry and Bloom’s split. On August 1, he judge agreed that Perry would not have to testify.
After years of legal woes surrounding the Montecito, California estate, the ongoing dispute between Perry and Westcott is finally nearing the end. A court ruling on November 25 has ordered Westcott to pay Perry $1.8 million in damages over lost rental income on the home, per People. In the months leading up to the trial, the “Roar” singer initially sought to be compensated for damages totaling the aforementioned costs of over $5 million in forfeited rental value and necessary repairs made on the home. After months of reviewing documents for the property, which included assessments and expert testimony, the judge agreed that Westcott owed Perry reimbursement, although for a lesser amount than she requested.
Official documents reviewed by People reveal that the payout accounts for $2.8 million in the property’s rental value during the deferred closing of the sale from 2020 to the stipulated due date in 2024, minus $150,000 in retained capital value, and $150,000 in lost interest on Westcott’s behalf. While Perry requested $2.2 million for the cost of restorations during the delay period, the ruling capped the amount to roughly $260,000, the exact amount Westcott had previously proposed. Additionally, Judge Joseph Lipner reportedly stated that since Gudvi, Perry’s business manager, paid Westcott $9 million and retained $6 million from the purchase, he can deduct the $1.8 million settlement from the remaining $6 million.
Though Perry and her ex-fiancé, Orlando Bloom, gained legal control of the Montecito dwelling months ago, it remains unclear whether the couple ever resided in the home before their split in June. It also has yet to be confirmed whether the victory for Perry would allow the pop star to keep the mansion without making further payment to Westcott, or if she is to owe the Texas millionaire and disabled veteran additional payment on the house.
Both parties are expected to appear at the final judgment hearing related to the settlement, which is reportedly scheduled for December 30. Gudvi is responsible for preparing the judgment, and the hearing will allow either party the opportunity to challenge the settlement “with a valid objection within the next ten days,” per Law Commentary.
The Roman Catholic Archdiocese deal
Back in 2015, Perry was at the center of a far more dramatic—and complex—case with the Roman Catholic Archdiocese of Los Angeles against the Sisters of the Immaculate Heart of Mary and their proposed purchaser, restaurateur Dana Hollister.
The property in question was a former convent in the Los Feliz neighborhood of Los Angeles. The eight-acre property includes more than 30,000 square feet of living space and dates back to 1927. Architect Bernard Maybeck designed the home, which was featured in a 1930 issue of AD. According to Insider, the Sisters of the Immaculate Heart lived there between the years of 1972, when the home was sold directly to them, per the Times, and 2011, when the Archdiocese forced the elderly Sisters to leave against their will. Though Perry is the big name in the middle of it all, it’s clear that the conflict over the property predated the singer’s involvement.
Archbishop Jose Gomez agreed to sell the convent to Perry for $14.5 million (with $10 million in cash) and the Sisters were concerned they wouldn’t receive any money from the sale. Gomez and Perry had a deal, but the Sisters insisted the property was theirs to sell and quickly sold it to Hollister for $15.5 million (with $100,000 in cash) before Perry’s deal was complete. Hollister promptly moved into the home. Both Gomez and Perry then sued Hollister, and in July 2015 a judge invalidated Hollister’s purchase, though he ruled she could continue living there if she paid $25,000 in rent to the Sisters.
There was plenty of back and forth squabbling—including Sister Catherine Rose Holzman telling Billboard, “Katy Perry represents everything we don’t believe in”—but in March 2017 the Los Angeles Superior Court ruled in favor of the archdiocese as the party with the right to sell, firmly invalidating Hollister’s purchase. You might think this is where it ends, but in order to buy the property, Perry would need to get final approval from the Vatican, as all property deals over $7.5 million require. Six months later, the Hollywood Reporter shared that the Vatican would not give approval until Perry found a replacement for the property’s House of Prayer.
In November 2017, Hollister was ordered to pay the archdiocese’s attorney fees of $3.47 million and $1.57 million to Perry’s company. A second phase of the trial was set to find if Hollister owed either party more in punitive damages. Hollister declared bankruptcy. In March 2018, two of the nuns, including the aforementioned Holzman, accompanied Hollister to bankruptcy court. In a final (tragic) twist, Holzman collapsed and died during the court proceeding.
It is unclear who owns the property today, but the site still hosts a House of Prayer run by the Archdiocese of Los Angeles.
