Vintage Rolex watches are making a huge comeback, with many successful auctions taking place just this year. Rolex watches like the one worn by icons Mercedes Gletize and those specially ordered by ultra-wealthy leaders of the world have recently sold for millions!
Many factors can contribute to these vintage watches selling for well over seven figures; such as rarity, historical significance, and the pedigree of the previous owner.
We have compiled a current list of the ten most expensive Rolex watches ever sold.
Paul Newman’s Rolex Daytona – $17.8 Million
The Rolex Daytona 6239 worn by the man credited with popularizing the model went up for auction by Phillips Auction in 2017.
Legendary actor, director and entrepreneur, Paul Newman's, reference 6239 carries a rich history. Prior to the Daytona model appearing on the actor’s wrist, it was a failing model. After the Daytona model's release, it was so poorly performing, in fact, that many authorized dealers were selling them at a major discount.
After Newman was pictured wearing the Daytona on the cover of magazines, the watch sky-rocketed in popularity.
This Daytona 6239 holds the #1 place as the most expensive Rolex ever sold. It was a gift to Newman by his wife, actress Joanne Woodward, and features a distinctive exotic dial and a personal engraving on the case back, reading “Drive Carefully Me.”
It sold for $17.5 million, making it not only the most expensive Rolex ever sold, but also the third most expensive watch sold ever.
Rolex Daytona 16599SAAEC - $6.8 Million
The off-catalog Rolex Daytona “Rainbow” is a highly sought-after model in modern day, with new models reselling for well over $400,000. The second most expensive Rolex ever sold is the "rainbow" model that started it all.
Sold by Philips in 2024, the Rolex Daytona “Rainbow” 16599SAAEC was the first “Rainbow” Daytona ever made, and is the only known reference of the model to appear in auction.
The creation of this model was a visionary choice in 1994, making Rolex the first to create such a configuration. It unknowingly predicted the popularity of rainbow-colored gems in luxury watchmaking, as the first ever “rainbow” sports model wristwatch.
The bezel is set with 36 rainbow-colored baguette-cut sapphires, featuring a diamond-encrusted dial and rainbow-colored sapphire hour markers. This model is exceptionally rare, as it was never mass produced and was apparently not acknowledged by Rolex until recently. This piece sold for $6.8 million.
Rolex “Stelline” 6062 - $6.2 million
Just this year, a stunning Rolex Oyster Perpetual 6062 “Stelline” went up for auction by the Monaco Legend Group, beating out the “Bao Dai” as the highest selling reference of this model.
The configuration of the “Stelline”—yellow gold case, black dial, 6 diamond hour markers, moonphase, and the original tile bracelet—was exceptionally rare. This Rolex was produced in the early 1950s, at a time when Rolex was playing with the design of their dress watches. Furthermore, it is only one of two vintage Oyster Perpetuals that included a moon-phase!
The watch was also in excellent condition, and sold for $6.2 million!
The Rolex Daytona 6265 “The Unicorn” – $5.9 Million
The Rolex Daytona 6265 known as “The Unicorn” was a rare white gold model produced in 1971, at a time where most watches were crafted in yellow gold or stainless steel.
“The Unicorn” features a black dial with three white subdials, white gold case, and a custom riveted oyster bracelet. It is also the only known manual-winding vintage white gold model in existence.
This 6265 is truly one-of-one and sold in 2018 for $5.9 million!
Paul Newman’s Rolex Daytona “Big Red” 6263 - $5.5 million
The Rolex “Big Red” Daytona 6263 owned by Paul Newman went up for auction in 2017 by Phillips.
This is already a highly sought-after Daytona 6263 model, as it maintains full originality with the “Big Red” dial. “Big Red” Daytona models that maintain originality from its time of production in the 1970s can sell for $70,000 to $120,000.
However, the value of the watch maintaining its originality is supercharged by the fame of the original owner. This watch features another special engraving on the case back, “Drive Slowly, Joanne,” reminding Newman to be careful while racing so he could make it home to his wife.
The beautiful story and historical significance of this watch is why it sold for $5,475,000 million.
Rolex Daytona 6270 - $5.23 Million
The Rolex Daytona 6270 “The King” went up for auction by Sotheby’s in 2025. It is an extremely rare model that was produced in the mid-1980s, with a diamond-encrusted champagne dial and baguette-cut diamond bezel.
“The King” is one of eight 6270s that were custom ordered from Rolex by the Sultan of Omar, Qaboos bin Said.
This stunning model is the highest mix of horology and luxury, as an 18k gold, precious-gem encrusted sports model, and sold for $5.23 million.
Rolex GMT Master 1675 - $5.1 Million
The Rolex GMT Master 1675, nicknamed “The Brando,” went up for auction by Christie’s in 2023. It was worn by Marlon Brando in the 1979 film Apocalypse Now, and features “M. Brando” engraved on the case back.
Part of what makes this watch so interesting is that Brando had the brown-colored bezel removed, so as not to be distracting in the film.
The pop-cultural significance of this piece is why it sold for $5.12 million!
The Bao Dai Rolex – $5.06 Million
Once owned by the last emperor of Vietnam, the Rolex 6062 “Bao Dai” is one of the rarest, most historically significant, and most visually striking vintage Rolex watches ever discovered.
It went up for auction in 2017 by Phillips, and was the watch owned by the final emperor of the Nguyễn Dynasty, Emperor Bảo Đại. He was known for living an opulent lifestyle, as exemplified by this Rolex.
The "Bao Dai" Rolex is a yellow gold Oyster Perpetual featuring a black dial with 5 diamond hour markers (placed on the even hours). It was an automatic movement with a triple calendar and moonphase. This configuration is truly one-of-one, with no other references having appeared with the same dial.
Its rarity and the historical significance of its previous owner is why it sold for $5.06 million!
Rolex Daytona 6270 - $4.1 Million
Another one of the Sultan’s custom Rolex Daytona 6270 “The King”s went up for auction by Phillips in 2025. This model sold for little over one million dollars less than the one listed above, and features a bit of oxidization on the bracelet. However, it was still in amazing condition. It had the original case back sticker, as the owner did not wear it much if at all, and sold for $4.1 million!
Rolex Paul Newman Daytona 6263 "Legend" - $3.7 Million
The Rolex Daytona 6263 “Legend,” went up for auction by Phillips in 2017.
This is only one of four known references, making it extremely rare. The 6263 features a lemon-yellow “Paul Newman” dial, aged pumpkin-colored lumes, subdials with square markers, and the “T Swiss T” inscription at 6 o’clock (indicating that the watch is made with radioactive tritium!).
It is considered one of the rarest and most beautiful Paul Newman Daytonas, maintaining 100% originality from its production in 1970-1971, and sold for $3.7 million!
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