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Luxury broker busted for allegedly using client homes to conduct sordid affair — as he’s sued by lover and her ex

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Luxury broker busted for allegedly using client homes to conduct sordid affair — as he’s sued by lover and her ex

By Mary K. Jacob Published July 1, 2026, 6:44 p.m. ET

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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. 

Luxury real estate broker Stephen Cipres, founder of Corcoran Pacific Properties, allegedly had sex with his assistant Sarah Dombrose at 10 to 20 client properties over four years, using listed homes rather than hotels for the encounters, according to deposition testimony. 5
Luxury real estate broker Stephen Cipres, founder of Corcoran Pacific Properties, allegedly had sex with his assistant Sarah Dombrose at 10 to 20 client properties over four years, using listed homes rather than hotels for the encounters, according to deposition testimony. Stephen Cipres at Corcoran Pacific Properties

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.

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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 (pictured) says the relationship began non-consensually and continued because she feared losing her job and income, while Cipres claims in his own defamation suit that she pursued him first and the relationship was fully consensual. 5
Dombrose (pictured) says the relationship began non-consensually and continued because she feared losing her job and income, while Cipres claims in his own defamation suit that she pursued him first and the relationship was fully consensual. Sarah Dombrose / Facebook

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.

One of the alleged trysts took place at the Coral Strand condo. 5
One of the alleged trysts took place at the Coral Strand condo. Google Maps

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.”

Another tryst allegedly took place at 1925 Kalakaua Avenue. 5
Another tryst allegedly took place at 1925 Kalakaua Avenue. Google Maps

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