22 Most Expensive Rolex Watches

Since the dawn of time, humans have been running late, showing up too early, and making it just in time. However, there’s only one way to be last at a party or first for dinner, and that’s in style with a dazzling Rolex timepiece. Of course, the perfect watch is the most expensive Rolex. There isn’t a person in the world that doesn’t know Rolex. Even people who tell time on their phones or use a sundial have heard of a Rolex watch. The global brand is synonymous with class, elegance, and style. 

Rolex makes watches that are top of the line and attract the wealthiest movie stars, celebrities, and collectors. Indeed, Rolex has cemented its place in history and its watches often sell at auctions for millions. The company produces some of the most expensive Rolex watches on the market. They feature the best materials, impressive parts, and beautiful style. The most expensive Rolex is the missing piece of every stellar outfit. 

Undoubtedly, the most expensive Rolex isn’t just for telling time. It’s to steal the spotlight and grab everyone’s attention when making a grand entrance. 

22. Rolex Submariner – $13,337

Rolex is renowned for releasing the most stunning and reliable watches in history. In 1953, they had everyone talking with the stylish Rolex Submariner. It got rave reviews and quickly became one of the most popular models. Of course, it helped that James Bond would wear the Rolex Submariner in his films.

The stellar timepiece was the first to allow divers to go 100 meters. It’s one of the most expensive Rolex watches and starts at $13,337. 

21. Sky-Dweller Oystersteel – $14,275

Traveling across the globe is both exciting and exhausting. It’s essential to have the perfect Rolex watch while seeing the world. Well, Rolex has you covered with the beautiful Sky-Dweller Oystersteel. Rolex designed the timepiece for travelers and pilots so they could keep track of two time zones. It features a central dial but with a second 24-hour dial-off center.

The Sky-Dweller starts at $14,275 and comes in white gold, rose gold, and yellow gold. The expensive Rolex might not be as popular but is perfect for tourists and pilots. 

20. Cosmograph Daytona – $16,780

Rolex’s history is often tied closely to the world of racing. Indeed, they released several watches for professional race car drivers. Enter the beautiful Cosmograph Daytona. Rolex first released the show-stealing timepiece in 1963 to rave reviews. It was a massive hit with race care drivers, but Hollywood stars and ordinary people also fell in love with it.

The trendsetting Rolex watch’s iconic dial became so popular that other brands copied it. The Cosmograph Daytona is the perfect watch to wear or add to a collection. It costs an incredible $16,780.

19. Rolex Datejust – $17,000

Rolex has been the dominant force in elegant watches for decades. Few companies are even on their level. In 1945, the Rolex Datejust debuted to commemorate the brand’s 40th anniversary. The expensive Rolex watch was an instant hit and remains popular today. The sleek Datejust costs $17,000 and comes in several sizes, including 31 mm, 34 mm, 36 mm, and 41 mm. The collection also includes the Lady-Datejust, which is 28 mm.

The beautiful timepiece is stainless steel and comes in yellow gold, white gold, and rose gold. It even comes with the option of adding stones onto the dial. Indeed, the slick Datejust is perfect for business people going for a casual or professional look. 

18. Rolex Day-Date – $34,500

The Rolex Day-Date timepiece is one of the brand’s classic collections. Indeed, Rolex released the original Day-Date in the late 1950s. At the time, it was one of the first waterproof watches with a calendar, day, and date display.

The stunning self-winding chronometer Rolex was also the first to include the President bracelet, also called the jubilee bracelet. Throughout history, famous celebrities, sports stars, and politicians rocked the expensive Rolex Day-Date. In 2021, Rolex released an updated version for $34,500.

17. Rolex Pearlmaster – $87,000

Rolex continues to roll out the most impressive watches to this day. Indeed, the Rolex Pearlmaster is one of the finest timepieces on the market and costs $87,000. It’s a customized version of the Rolex Datejust watch and comes in rose gold, yellow gold, and white gold.

Rolex tops off the stunning watch with sparkling diamonds and dazzling gems. The waterproof Rolex is top of the line with cutting-edge techniques. Indeed, it’s one of the newest and most expensive Rolex watches.

16. Rolex GMT Master II – $173,999

Rolex 0ften honors its rich history and updates classic collections from the past. For instance, the Rolex GMT Master II can trace its history back to the original GMT Master II, released in the 50s and 60s. At the time, the beautiful timepieces were a hit with movie stars, sports icons, pilots, and astronauts.

Rolex continues to update the Master GMT II due to its immense popularity. In 2021, Rolex released the new line of GMT Master II watches for $173,999. The gorgeous watch comes in a rose gold case containing oyster steel and 18-karat yellow gold. The GMT Master II is the most expensive Rolex watch in the current collection. 

15. Steve McQueen 1967 Rolex Submariner – $234,000

The King of Cool, Steve McQueen, was one of Hollywood’s biggest stars in the 60s and 70s. Indeed, his coolness transcends time. Of course, it helped that he had great taste in Rolex watches. McQueen’s 1967 Rolex Submariner was a basic Rolex featuring a date display, water resistance, and a stainless steel band.

McQueen often wore the gorgeous timepiece around town and in several films, including the 1971 movie Le Mans. In 2009, the vintage watch sold for $234,000 at the Antiquorum auction. It’s likely increased in value since then and could go for three times as much now. 

14. Rolex Platinum Diamond Pearlmaster – $277,850

Rolex is always looking for new ways to present innovative yet sleek and elegant timepieces. Of course, they never disappoint. In 2011, the Rolex Platinum Diamond Pearlmaster hit the market to rave reviews and cost $277,850. The limited edition Pearlmaster is part of the rare Day-Date collection.

It boasts two large diamonds at six and nine o’clock with a silver dial in a platinum case. However, the highlight of the luxury timepiece is the meteorite diamonds on the custom bezel. Indeed, it features 42 dazzling diamonds, which makes it one of the most expensive Rolex watches. 

13. 1972 James Bond Rolex Submariner – $365,000

James Bond’s 1972 Rolex Submariner is the most expensive Rolex watch that can’t tell time. The stunning timepiece sold for an unbelievable $365,000 at the 2015 Philips auction. Roger Moore wore the watch as James Bond in the 1973 classic Live and Let Die. The Rolex Submariner consists of stainless steel with a black dial and “Roger Mooe 007” engraved on the back.

However, the production crew modified the Rolex so much it’s just an expensive prop now. Still, the gorgeous watch stole the show twice in the film. First, the film changed the bezel to a buzzsaw, which Bond uses to cut a rope. At another point, he unzips Mrs. Caruso’s dress using the Rolex’s magnetic power. 

12. Rolex Sea-Dweller – $414,000

Rolex often created custom timepieces for celebrities, sports stars, and the wealthiest watch collectors. Indeed, the Sulton of Oman loved watches and was an enthusiastic collector. In 1977, the company made the Golden Khanjar Sea-Dweller Rolex for Sultan Qaboos bin Said al Said.

The unique watch has Oman’s national emblem, the Khanjar, engraved on the dial at the six o’clock position. It matches the white coronet at the noon position. The expensive Rolex sold for an incredible $414,000. 

11. Rolex Oyster Perpetual – $440,000

The stunning Oyster Perpetual Rolex is the first to feature 18-karat gold instead of the traditional stainless steel. Indeed, this dial boasts black, blue, and yellow colors to compliment the large gold numbers. In 1950, the first President of India, Dr. Rajendra Prasad, received the expensive Rolex as a gift on the country’s first republic day.

Rolex engraved the date and a map of India connecting with Nepal and Afghanistan on the dial. However, the $440,00 Rolex disappeared from the Prasad family watch collection and showed up at the Sotheby’s auction in 2011. The family was able to stop the sale of the watch through petition. 

10. Rolex GMT Master II Ice – $485,350

During the 14th Dubai International Sports Conference, iconic footballer Cristiano Ronaldo stole the spotlight with his dazzling Rolex GMT Master II Ice. It comes in an 18-karat white gold oyster case with 30 carats of sparkling diamonds. Plus, the dial features a striking gold and diamond pattern.

It also boasts a waterproof case with a GMT 24-hour time zone dial. The Rolex Master Ice is one of the most expensive Rolex watches of the last few years. Indeed, the stunning timepiece goes for $485,350. 

9. Rolex Stelline Gold – $895,000

Few timepieces compare to the sleek and gorgeous Rolex Gold watch. In 2015, the expensive Rolex sold for a shocking $895,000. The stunning Rolex hit the market in 1950 and comes in stainless steel yellow gold with a water-resistant oyster case.

It was also the first automatic Rolex to have a triple calendar, moon phase, day, and date display. The highlight of the vintage timepiece is the small star hour markers. Indeed, watch collectors gave it the nickname Stelline, which translates to small star. 

8. Jack Nicklaus Rolex Day-Date – $1.2 Million

World-renowned pro golfer Jack Nicklaus wore his expensive Rolex Day-Date watch when he won 12 of 18 PGA world championships. The stylish watch comes in an 18-karat yellow gold case on a President bracelet. It’s also the first watch to have the date and day display spelled out on the dial.

Speaking of the dial, it comes in a rare pie-pan color with baton hour markers resembling golf trees. In 1967, Rolex gifted the timepiece to Nicklaus, and he wore it for the next 50 years during every competition. In 2019, Nicklaus’ Rolex Day-Date sold at the Philips auction house for $1.2 million, with all proceeds going to the Nicklaus Children’s Health Care Foundation. 

7. Eric Clapton’s Rolex Cosmography Daytona – $505,000

At one time, legendary musician Eric Clapton owned one of the most expensive Rolex watches sold at an auction.  Clapton’s Rolex Cosmograph Daytona, aka Oyster Albino, is one of the most famous Rolex watches.

In 2002, the stunning timepiece sold for $505,000 at a Sotheby’s auction in New York. It sold for a second time at the Phillips auction for an incredible $1.5 million in 2015. Clapton’s Rolex is one of four that has a single white color for the dial. It comes in a stainless steel case and is Caliber 727 powered. 6. Marlon Brando’s

6. Apocalypse Now Rolex GMT-Master – $1.9 Million

In 1979, Marlon Brando starred in the classic Francis Ford Coppola film Apocalypse Now. Brando gave a stellar performance that critics still talk about to this day. Viewers with a keen eye notice Brando’s wearing a stunning 1972 Rolex GMT-Master during the movie.

It’s a simple black watch with glowing hour markers and hands with a golden shine. It doesn’t include the bezel, as Coppola asked Brando to remove it during filming. However, Brando did carve his initials on the back of the vintage timepiece, making it one of the most expensive Rolex watches. The phenomenal Rolex sold for an astounding $1.19 million at the 2019 Phillips Game Changers auction.

5. Rolex Antimagnetique – $3.5 Million

The 1942 Rolex Antimagnetique is so rare that only 12 watches are still around today. At that time, Rolex was heavily involved with racing and offered the Antimagentique as a gift to winning teams. The stunning stainless steel timepiece comes in a large 44 m case with pink-colored Arabic and baton hour markers. It also boasts a blue telemeter and black tachymeter scale on the dial.

In 2013, the gorgeous vintage watch sold for $1.16 million at Christie’s auction house. However, three years later, the watch increased in value and sold for an impressive $2.5 million at Philips auction house in Switzerland.

4. Rolex Bao Dai – $5.1 Million

In 2017, the slick Bao Dai Rolex sold at Phillips auction house for a mind-blowing $5.1 million. This particular Rolex is dubbed “The Keeper of Greatness” and is only one of three versions created. However, this Bao Dai is the only one to feature diamond markers around the black dial. The rare Rolex comes in a gold oyster case with a full calendar.

It also has a fascinating backstory that starts in the 1950s. The first owner of the expensive Rolex Bao Dai was the last emperor of Vietnam, Nguyễn Phúc Vĩnh Thụy. The timepiece remained in the family for decades until they sold it in 2002. 

3. Paul Newman’s Big Red Rolex Daytona – $5.4 Million

Throughout movie history, many celebrities have rocked a stylish and expensive Rolex. However, Hollywood legend Paul Newman is synonymous with the Rolex brand. Indeed, several of his Rolex watches have sold for an astronomical price.

In 2020, Paul Newman’s Daytona or Big Red sold for $5.4 million at an auction hosted by Aurel Bacs. Newman proudly wore the Rolex for 25 years. His wife, Joanna Woodward, gifted the vintage Rolex Daytona to her husband with the engraving, “Drive Slowly, Joanna.” In 2008, Newman’s daughter Clea received the watch as a gift. Eventually, Clea allowed her father’s watch to go up for sale at the auction. 

2. Rolex Unicorn Oyster Cosmograph – $5.9 Million

There’s a reason the Rolex Oyster Cosmograph is called the unicorn. It’s one of the rarest and most expensive Rolex watches in the world. At the time, Rolex made the Daytona with stainless steel, but there are a few exceptions.

The 1970 Rolex Oyster Cosmograph is the only one to feature 18-karat white gold with silver graphics, a black background, and a black sigma dial. The gorgeous watch first appeared in 2013 as part of John Goldberger’s collection. Later, the timepiece sold for an astonishing $5.9 million in 2018. Goldberger donated the money from the sale to the Children Action Foundation.

1. Paul Newman’s Rolex Daytona – $17.8 Million

Iconic actor Paul Newman’s Daytona sold for a whopping $17.8 million in 2017 at the Phillips auction house. The expensive Rolex first hit the market in the 1960s and features a tachymeter attached to the bezel, 300 units-per-hour stainless steel bezel, and three sub-dials with block markers. The sleek and rare Rolex also has 18,000 beats-per-hour movements. 

ddHowever, the watch is iconic and expensive because of its unique backstory. Newman’s wife, Joanne Woodward, gifted him the Rolex and engraved it with “Drive Carefully Me.” Paul Newman often wore the stunning Rolex while racing and in several films, most notably, in the 1969 movie Winning. It’s easily the most expensive watch sold at an auction.