Stephen Cipres, founder of Corcoran Pacific Properties, is accused by former assistant Sarah Dombrose of engaging in a years‑long sexual relationship that occurred inside 10–20 homes he was selling. Dombrose says the encounters were humiliating and that she felt compelled to comply to keep her job; Cipres admits the relationship but denies coercion and has filed a defamation suit. Corcoran Pacific severed ties with Cipres, who now brokers through Elite Pacific Properties, and multiple civil lawsuits related to the allegations remain pending.
Hawaii Broker Faces Lawsuits After Ex‑Assistant Alleges Sex Inside Client Homes

A prominent Hawaii real estate broker is facing multiple civil claims after his former assistant accused him of engaging in a years‑long sexual relationship that took place inside homes he was hired to sell.
Allegations and Legal Filings
Honolulu Civil Beat reported on July 1 that court documents in ongoing litigation allege Stephen Cipres, founder of Corcoran Pacific Properties, had sexual encounters with his assistant, Sarah Dombrose, at between 10 and 20 listed properties over a roughly four‑year period. The filings include competing lawsuits: Dombrose’s estranged husband, Matthew Gillespie, has sued Cipres alleging the broker damaged his marriage, while Cipres has filed a defamation complaint against Dombrose. Dombrose has also filed for divorce from Gillespie.
Details From Depositions And Affidavit
In deposition testimony, Cipres acknowledged paying Dombrose substantial sums for her work, producing checks of $34,000 and $50,000 among other large payments, according to the report. Dombrose describes the intimate encounters as degrading and says the relationship began soon after she was hired. In court filings, she states Cipres sometimes had her lie on a towel inside clients’ homes and that encounters often occurred before or after open houses or in parked cars.
“It felt like a chore. I felt really, like, a sex worker,”
“I did not want to perform oral sex and only did so because I believed refusing would cost me my job and income,”
In an affidavit cited by the outlet, Dombrose says she felt financially pressured to continue the relationship, which she alleges happened multiple times a week during normal business hours.
Response And Current Status
Cipres does not dispute that a sexual relationship occurred but denies any coercion, asserting in his defamation filing that he "never pressured, compelled, or coerced Dombrose" and that she initiated their first intimate encounter. Corcoran Pacific has cut ties with Cipres; Paul Roy, a principal agent at the firm, said he told Cipres to resign or be terminated after the allegations emerged. Cipres is now listed as working through his own brokerage, Elite Pacific Properties.
The competing civil suits remain active, and the allegations are disputed. This report summarizes the claims and responses as described in court documents and reporting by Honolulu Civil Beat.
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