Among the highlights is a rare stainless-steel Rolex reference 6062 from 1955, featuring a triple-calendar moonphase and an unusual two-tone Explorer dial.
The watch, previously owned by renowned collector John Goldberger, is estimated at between €1 million and €2 million.
Patek Philippe will also feature prominently, with a reference 2499 perpetual calendar chronograph estimated at €700,000 to €1.4 million and a reference 3974 minute repeater valued at between €600,000 and €1.2 million.
Other notable pieces include rare Vacheron Constantin watches, a platinum Audemars Piguet triple-calendar and eighteen Cartier watches spanning the brand’s design history.
Ahead of the auction, the collection has been exhibited in Geneva, Hong Kong, Milan, New York and Bologna.
Public previews will take place at Le Méridien Beach Plaza on Thursday 29 October from 11am to 8pm and Friday 30 October from 10.30am to 8pm, with additional viewing opportunities on Saturday and Sunday from 10am to 12.30pm.
Both auction sessions will begin at 2.30pm.