The Vintage Rolex Watch That Could Be Worth $75,000 In 2025

About a century ago, Rolex rolled out the world's first waterproof watch, the Rolex Oyster. To market it, Mercedes Gleitz wore one during her 10-hour swim across the English Channel in 1927. When the swim was over, the watch was still ticking, a fact the company later publicized in a full-page advertisement in Britain's Daily Mail newspaper, according to Rolex's historical webpage. In 2025, a watch inspired by that original Oyster - the Rolex "Double Red" Sea-Dweller — was listed for sale on watch website Chrono24 for $74,995.

Following the success of the original Oyster, Rolex would go on to produce at least two dive "Oyster case" watch brands capable of withstanding severe underwater pressures. One of these was the Submariner. Its first model, which hit the market in 1953, could withstand pressures of 100 meters. Later models, developed in the 1960s and 1980s, were capable of withstanding depths of 300 meters, or 1,000 feet.

But French deep diving company Compagnie Maritime d'Expertises (COMEX) wanted something that could dive even deeper. So, COMEX worked with Rolex to create a watch that could be submerged at 2,000 feet, or 610 meters, according to Bob's Watches, a website that specializes in analyzing and selling Rolexes. The first model available for sale from that collaboration, the Sea-Dweller Ref. 1665, came out in 1967 and had two lines written in red. It's this "Double Red" that can now fetch a small fortune.

The most common characteristic of the Double Red are two red lines beneath the watch's hands that say "Sea-Dweller" and "Submariner 2000." Below those two red lines, written in silver, are three lines "2000 ft = 610m," "Superlative Chronometer," and "Officially Certified." The Sea-Dweller was a "souped-up version of the Submariner," Bob's Watches explained, with a patented Helium Escape Valve and a thicker case and domed crystal. The Double Red also had engravings on the back such as "Rolex," "Oyster," "Gas Escape Valve" and "Patent" though the writing would vary depending on the model.

In regards to prices, pre-owned Sea-Dweller models in good condition can be worth at least $7,000. But a Double Red Sea-Dweller can command prices of well over $50,000. DRSD watches listed for sale on Chrono24 ranged from just below $34,000 to well over $132,000.

But the most valuable Sea-Dweller watch of all is the Rolex Single Red Sea-Dweller, which has a single line written in red that says "Sea-Dweller." This was an early prototype watch that was only given to deep sea divers. Just a dozen Single Reds are known to exist, per Bob's Watches, with the highest selling one sold for $700,000 in 2018.

In the decades since its founding in 1905, Rolex would come out with brands and innovations that are still prized today, making its older vintage watches potentially worth a ton of money. But just like old historical photographs or sports collectibles that may grow more valuable with time, the value of a vintage Rolex depends on its condition, historical significance, and rarity.

Indeed being limited in number is what makes models such as Rolex's "Paul Newman" Daytona (crafted for race car drivers) or the Double Red Sea-Dweller does have the "distinct features that set them apart from regular models" that can make them extremely pricey, according to a blog by California-based jewelry retailer Happy Jewelers. Another important feature for value is authenticity, which is why Rolexes that still have their original cases, dials, and hands can obtain higher prices.