Add The New York Post on Google A former Hawaii real estate mogul turned other people’s dream homes into his own private playground for a four-year affair with his assistant, according to shocking new court documents obtained by Honolulu Civil Beat.
Stephen Cipres, who founded and once ran Corcoran Pacific Properties, allegedly had sex with employee Sarah Dombrose inside 10 to 20 homes he’d been hired to sell, skipping hotels in favor of client properties, deposition testimony reveals.
Cipres hasn’t disputed the broad strokes of the affair, though he insists it was consensual and claims Dombrose came onto him first.
The saga has since spiraled into a tangle of lawsuits.
Dombrose’s estranged husband, Matthew Gillespie, is suing Cipres for wrecking his marriage. Cipres has countersued Dombrose for defamation, accusing her of falsely claiming she was coerced. Dombrose, for her part, has already filed for divorce.
Corcoran Pacific has since cut ties with Cipres, who founded the brokerage himself. Principal agent Paul Roy said he gave Cipres an ultimatum after learning of the admissions in deposition testimony.
“The minute I found out about it, I told Stephen that he either needed to resign or I would terminate him,” Roy told Honolulu Civil Beat.
“I feel bad for our brand. I feel bad for our agents. I mostly feel bad for our clients who expected professionals to act in a professional manner.”
Dombrose went to work for Cipres in 2021 as a newly licensed agent, according to her affidavit, juggling three kids and a rocky marriage while desperate for income. She became Cipres’ exclusive assistant, covering open houses and handling other tasks, with Cipres cutting her checks from a personal account.
The alleged abuse began early, Dombrose says, at an open house in the oceanfront Coral Strand condos on Oahu’s Gold Coast, where she claims Cipres kissed her without consent and pulled her into a hallway.
“I felt obligated to perform oral sex on him to keep my employment,” Dombrose testified. “I did not want to perform oral sex and only did so because I believed refusing would cost me my job and income.”
What followed, she says, was years of unwanted encounters squeezed into open house windows and parked cars.
“Because of my precarious financial situation, I felt that I had little choice but to continue engaging in sexual relations with Cipres, which often occurred multiple times each week during normal business hours, frequently at listed properties before or after open house events or in one of our parked cars,” she said.
Cipres allegedly never took her to a hotel, or to any property he and his wife Lisa actually owned, instead outfitting the trysts with towels borrowed from clients’ linen closets. He compensated her handsomely along the way, cutting checks as large as $50,000 to his assistant, his deposition shows.
“It felt like a chore,” Dombrose said. “I felt really, like, a sex worker.”
Cipres, in his own deposition, didn’t flatly deny the encounters but was cagey on specifics, at one point answering “possible but I’m not sure” when asked whether sex with Dombrose occurred during the years in question.
Cipres tells a very different story in the defamation suit he filed against Dombrose this month, claiming she leaned on him emotionally over her failing marriage before making the first move.
“The Plaintiff never pressured, compelled, or coerced Dombrose into either starting or maintaining their relationship,” the complaint states. “In fact, Dombrose initiated their first intimate encounter.”
Gillespie’s suit, filed last July through attorney Bosko Petricevic, names Cipres, Corcoran Pacific and The Corcoran Group as defendants, alleging emotional distress, failure to supervise and civil conspiracy. A judge tossed Gillespie’s claim for “alienation of spousal affection” in January 2025 but let the rest proceed.
Cipres has since lost a bid to seal the deposition transcripts, with a Honolulu judge denying the request in late May. Lawyers for The Corcoran Group tried again last week to keep the records under wraps, warning in a court filing that Civil Beat planned to quote directly from the sealed testimony.
But the brand behind the “For Sale” signs wants nothing to do with the mess. Both Corcoran Pacific and its parent franchisor The Corcoran Group have distanced themselves from Cipres, insisting he operated as an independent contractor beyond their control.
Corcoran Group litigation counsel Sean Campbell dismissed the company’s inclusion in the suit as baseless in correspondence with Gillespie’s attorney.
Petricevic isn’t buying the defense, especially given that Cipres was Corcoran Pacific’s founder, president and shareholder, not just a rank-and-file agent.
“The notion that the owner and president of the company is an independent contractor is laughable,” he said. He added that he’d flagged the allegations to Corcoran two years ago, saying, “They knew about it for two years, and for two years they’ve said they had nothing to do with it. They chose to put their head in the sand, and the homeowners suffered.”
Despite acknowledging in his deposition that using a client’s home for sex wasn’t ethical, Cipres has faced no discipline.
A spokesman for Hawaii’s Department of Commerce and Consumer Affairs confirmed his broker’s license remains valid and that no complaints have been filed against him.
Cipres now runs his own brokerage, still selling multimillion-dollar properties.
Cipres and Dombrose did not immediately respond to The Post’s request for comment.
