Hawaii Real Estate Broker's Luxury Listings Became Secret Affair Locations

When a real estate agent says a property has“great bones”and“lots of character,”they usually mean the architecture. But for Stephen Cipres, founder of Corcoran Pacific Properties, the luxury homes he was showing became something far more problematic — the backdrop for a years-long affair with his executive assistant.

According to legal documents obtained by Honolulu Civil Beat, Cipres and Sarah Dombrose allegedly used 10 to 20 of his client properties, plus their cars, for sexual encounters spanning roughly four years. The details emerging from court filings paint a troubling picture of workplace power dynamics gone wrong. Dombrose, who began working for Cipres in 2021, claims the relationship started without her consent when he kissed her at an open house. In her affidavit, she testified that she felt obligated to continue the relationship — and specifically obligated to perform oral sex — because her financial situation was precarious. A single mother of three navigating a rocky marriage, she needed the job to survive. Records show Cipres would cut her $50,000 checks periodically, which raises uncomfortable questions about whether those payments were compensation, coercion, or both.

Cipres hasn’t denied the affair. Instead, he’s flipped the script entirely, claiming the relationship was entirely consensual and that Dombrose initiated it. He’s now suing her for defamation and false accusations of coercion, while her estranged husband, Matthew Gillespie, has sued Cipres for emotional distress and the destruction of his marriage. Dombrose has filed for divorce. Corcoran Pacific Properties severed ties with Cipres, though he continues to sell homes through Elite Pacific Properties.

What makes this case particularly emblematic of a broader problem is how it weaponizes workplace hierarchy and financial vulnerability. Whether or not a jury eventually accepts Cipres’s version of consensual romance, the foundational power imbalance — employer-employee, financial security on the line, vulnerable personal circumstances — makes the“she came onto me first”defense feel hollow. The story also reveals something uncomfortable about luxury real estate itself: those stunning homes that clients are eager to list become, in this case, private spaces where a boss and his assistant’s relationship unfolded across normal business hours.

The fact that Corcoran Pacific moved quickly to distance itself from Cipres suggests they understand the reputational and legal exposure. But the real estate world, like many industries built on personal relationships and closed-door dealings, will likely need a harder look at how power operates behind those glossy listings.