From Hollywood royalty to actual royalty, Rolex watches have been the ultimate status symbol worn by tastemakers and high society alike for over a century. While most Rolexes hold value remarkably well, most expensive Rolex have sold at auction for mind-boggling sums that reflect their unmatched rarity and provenance.
Get ready to discover the crème de la crème – the most valuable, coveted, and downright iconic Rolex timepieces to ever grace a wrist. The eight watches below represent the highest echelons of horology, from important historical milestones to celebrity connections driving prices into the stratosphere.
For watch enthusiasts, owning one of these stratospherically priced Rolexes is akin to possessing a Rembrandt or a vintage Ferrari GTO. Beyond investment potential, they represent the pinnacle of the world’s most recognized luxury watch brand. So feast your eyes on the Mona Lisa’s of Rolex collecting!
8 Most Expensive Rolex
1. Paul Newman’s Rolex Daytona:
Price ranges from $190,000 to $950,000 with the highest sale price at $17.75 million
The Rolex Daytona reference 6239 worn by Paul Newman is one of the most famous and sought-after vintage Rolex watches of all time. Newman received the watch as a gift from his wife Joanne Woodward in the late 1960s, and it soon became his signature timepiece both on and off screen.
This particular Daytona nicknamed the “Paul Newman Daytona,” stands out for its exotic dial with art deco-style numerals in a bold, easy-to-read font. The dial has a creamy, silvery-white color and three contrasting black subdials for the small seconds, 30-minute, and 12-hour registers. The indices are marked with simple black batons except for the 12, 3, 6, and 9 positions, which have rectangular markers.
At 37mm, the stainless steel case is relatively modest in size, especially by modern standards. The pump-style pushers on the right side of the case activate the chronograph function, while the winding crown is screwed down for water resistance. On the back, the caseback is stamped “ROLEX OYSTER” with the reference 6239 and serial number engravings.
The Oyster bracelet provides a secure and comfortable fit on the wrist. Rolex used stainless steel for the entire bracelet construction. The deployment clasp has the Rolex name elegantly engraved on the exterior.
Inside the case, the Valjoux 72 manual winding movement powers the timekeeping and stopwatch functions. This is the same movement used in early Cosmograph Daytonas up until the late 1980s. The watch achieves chronometer-level accuracy, an important hallmark of Rolex’s precision engineering.
In mint condition, the Paul Newman Daytona can fetch over $200,000 at auction. But beyond the monetary value, it represents one of the enduring style icons not just in timepieces, but menswear as a whole. The exotic dial and famous original owner have cemented its place in watchmaking history. For collectors and Paul Newman fans alike, the Paul Newman Daytona stands in a league of its own.
2. Rolex GMT-Master II
Costs between $10,750 to $115,000 and reached the highest sale price of $1.9 million
When it comes to iconic travel watches, the Rolex GMT-Master II is the quintessential pilot’s watch perfected. Designed in collaboration with Pan American Airways in the 1950s, the GMT-Master was the first watch capable of displaying two time zones simultaneously.
Today’s GMT-Master II carries on this legacy in the modern Rolex catalog. Inside the 40mm Oyster case, the Swiss-made caliber 3285 perpetual movement powers an additional 24-hour hand to display a second time zone in tandem with the conventional 12-hour hand. The red and blue bezel provides the signature look, allowing you to easily set it to a different timezone.
While functionally similar to the original, the current GMT-Master II features Rolex’s contemporary refinements. The case uses 904L steel for superior corrosion resistance. The sapphire crystal is virtually scratchproof. The re-engineered Oyster bracelet with polished center links has the Easylink extension system for adjusting on the fly.
When it comes to style options, Rolex offers several dial and bezel combinations from the classic black and blue “Batman” to the green “Hulk” and more. No matter which configuration you choose, the GMT-Master II pairs elegance with globetrotting practicality.
Of course, few watches reach icon status without the right image. On the wrist of legendary figures like Chuck Yeager, Bill Gates, and Daniel Craig’s James Bond, the GMT-Master epitomizes the stylish and worldly explorer. Whether cruising at 30,000 feet or navigating a new city, the Rolex GMT-Master II brings versatile, sophisticated utility
3. Rolex “President” Day-Date:
Priced from $37,450 to $277,000 and sold at a peak of $1.2 million
The Rolex Day-Date nicknamed the “President” in the watch community, stands as one of the most expensive Rolex and recognizable prestige timepieces of all time. First introduced in 1956, the Day-Date was a groundbreaking watch for being the first self-winding chronometer from Rolex with a calendar display that spelled out both the day of the week and the date.
The quintessential President configuration consists of the 18kt yellow gold case paired with the matching gold “President” bracelet. The bracelet earns its moniker from various US Presidents wearing Rolex Day-Dates on their wrist during their time in office, including Lyndon B. Johnson, Dwight D. Eisenhower, and Ronald Reagan.
Inside the 36mm Oyster case, Rolex equipped the Day-Date with the calibre 3155 self-winding movement entirely engineered and manufactured in house. The movement architecture provides accuracy ratings to chronometer specification and reserves approximately 48 hours of power reserve when fully wound.
Of course, the dial captures immediate attention with its contrasting mix of materials. The background is solid gold to match the case. Applied gold Roman numeral hour markers add classic elegance. At 12 o’clock, the Rolex crown logo subtly reminds you of the watch’s prestigious origins. The day of the week sits above the hallmark window date display for sharp legibility in 26 different languages.
Whether on the wrist of a head of state or captain of industry, the Rolex Day-Date President projects refinement, success, and taste. For over six decades, the iconic gold Day-Date remains a staple in Rolex’s most prestigious watch collections. With its versatile styling and Rolex pedigree, the Day-Date President makes a timeless statement.
4. Rolex “Unicorn” Daytona Reference 6265
A unique piece that fetched $5.9 million.
The Rolex Daytona reference 6265, nicknamed the “Unicorn” among collectors, stands out as one of the rarest and most coveted vintage Rolex chronographs ever produced. Manufactured for only 3 years from 1970 to 1973, the reference 6265 represented a transition model from the manual wind Daytonas to the automatic Daytona powered by the El Primero movement.
The Unicorn name stems from its peculiarly shaped chronograph pushers, which curve downwards compared to the straight pushers found on other vintage Daytonas. The stainless steel 40mm case paired with the black acrylic bezel exudes vintage 1970s style, while the contrasting silver dial and black subdials provide striking legibility.
Inside, the Valjoux 727 manual wind movement powers the chronograph function. Rolex modified it to beat at a faster 19,800 vph frequency for improved timing precision. The movement is hand-finished with polished bevels and Geneva stripes across bridges and levers.
Rolex produced the reference 6265 in extremely small numbers, estimated to be around 500 examples in total. Finding one in good condition has become next to impossible, driving prices up to $300,000 to $500,000 at auction when they rarely appear.
For Daytona aficionados, the reference 6265 represents the pinnacle of vintage Rolex chronographs. Its rarity and unusual design details make the Unicorn one of the most prized watches for serious collectors. When one becomes available for purchase, it generates buzz throughout the entire watch community thanks to its legendary status.
5. Rolex Reference 6062 “Bao Dai”
Has a price range of $50,000 to $400,000 with a record sale of $5.06 million
The Rolex Reference 6062, known as the “Bao Dai” after its original owner, stands out as the rarest and most valuable Rolex ever produced. Only 3 examples are known to exist, with the Bao Dai currently holding the record for the most expensive Rolex sold at auction, fetching over $5 million in 2017.
This ultra-rare reference released in 1954 stands apart for its black dial and diamond indexes. The diamonds at the even hours are set in triangular bezel formations, while the odd hour markers feature solitary diamonds. This creates a brilliant contrast between the elaborate diamonds and the deep black dial.
Inside the massive 38mm yellow gold Oyster case, Rolex equipped the Bao Dai with the finest movement available at the time, the automatic caliber 655. Beating at 18,000 bph, the rhodium-plated movement featured a power reserve of over 2 days thanks to two mainspring barrels.
Rolex made the Bao Dai from 18k yellow gold from case to bracelet. The lugs have an uncommonly wide design that adds to its imposing wrist presence. The screw down Oyster case back ensured water resistance, a feature still associated with Rolex’s legacy of rugged reliability.
For collectors, the “Bao Dai” stands at the pinnacle of rare vintage Rolex watches. Its imperial provenance, limited numbers, and record-breaking auction price cement its status as the holy grail for serious Rolex collectors. The Bao Dai represents a watchmaking treasure few will ever behold in person.
6. Rolex Daytona Oyster Reference 6263
Commands prices between $88,163 to $227,481, with the highest sale at $3.7 million
Debuting in 1969, the Rolex Daytona reference 6263 represents one of the most coveted and well-respected vintage chronographs from the legendary Swiss watchmaker. It was one of the last manual-wound Daytona models produced before the automatic movement was introduced in 1988.
The 40mm Oyster case rendered in stainless steel provides robust protection for the Valjoux 727 movement ticking inside. All the 6263 models feature a black bezel and screw-down pushers for excellent water resistance. The clean 3-register layout with black sub-dials contrasts nicely with the silver-white dial for instant legibility.
While similar to other vintage Daytonas preceding it, the reference 6263 innovated with a few key enhancements. It upped the beat rate to 21,600 bph for better timekeeping. The movement now included a clutch system for the chronograph to allow hand winding. Rolex also fitted a new bezel with an acrylic insert.
Later nicknamed the “Big Red” for the vibrant red Daytona label above the sub-dial at 6 o’clock, the reference 6263 had a relatively short production run of just 5 years. Finding one in such pristine condition is the ultimate goal for serious Rolex vintage collectors.
The reference 6263 represents Rolex perfecting the manual Daytona just before the automatic era transformed the model. For vintage watch enthusiasts, the Rolex chronograph does not get any more sought-after and valuable than the Daytona 6263 “Big Red”.
7. Rolex Submariner:
Generally ranges from $10,000 to $1 million, with a record sale price of $1.06 million.
Introduced in 1953 as Rolex’s first diver’s watch, the Submariner has earned an unrivaled reputation as the quintessential diving timepiece. Its design defined the genre and set the standard that all other dive watches aspire to match.
Inside the 40mm stainless steel Oyster case, Rolex equips the Submariner with a self-winding perpetual movement entirely manufactured in-house for precision timekeeping. The unidirectional rotating bezel with engraved markings allows divers to time their descent and ascent. The black dial provides excellent legibility underwater, with the Mercedes-style hands and Chromalight lume ensuring visibility in dim conditions.
Over the decades, Rolex has continually improved the Submariner while retaining the core attributes that made it an icon. The latest models use 904L steel for the case and bracelet, providing corrosion resistance when diving in saltwater. The sapphire crystal is virtually scratchproof, and the Oyster bracelet can be fine-tuned with the Glidelock extension system.
While engineered for diving, the Submariner’s rugged yet refined aesthetic makes it perfectly suitable outside the water. On the wrist of Naval officers, amateur divers, and James Bond, the Rolex Submariner represents the ultimate adventure watch. It remains one of Rolex’s most recognizable and widely respected models more than half a century after its debut.
8. Rolex Paul Newman Daytona “Oyster Sotto” Ref. 6263:
Valued between $600,000 to $1 million with a top auction price of $1.66 million
The Rolex Daytona reference 6263, nicknamed the “Oyster Sotto” by collectors, stands out as one of the rarest Paul Newman Daytona models ever produced. Made for only 2 years from 1970-1971, the Oyster Sotto featured an exotic black acrylic bezel and a distinctive “OYSTER” label printed below the Daytona text on the dial.
At 37mm, the Oyster case provided a waterproof enclosure for the venerable Valjoux 727 chronograph movement ticking inside. While similar to other vintage Daytonas of the era, the Oyster Sotto had a depth rating of 165 feet thanks to its screw-down pushers and Triplock winding crown
The art-deco style numerals on the creamy silver dial, along with the inky black subdials, create a perfect contrast. When Paul Newman himself wore this model, it became forever associated with his name and cemented its place in pop culture.
With only a few hundred pieces made, finding a Paul Newman Oyster Sotto in collectible condition is akin to a treasure hunt. But for those who acquire this grail, the chance to own a watch once worn by a legend is what places this Daytona in a class of its own. It represents the peak of vintage Rolex chronographs and Newman’s impeccable style.