Patek Philippe ref. 1518 Perpetual Calendar Chronograph (lot 48). Photographer: Stephen Pulvirent/Bloomberg Business
The Patek Philippe ref. 1518 is the grandaddy of all perpetual calendar chronographs—the original megawatch. This example was made in 1951 and sold two years later, making it a really late example (the watch went out of production in 1954 after nearly a decade and a half). Notice that the tachymeter scale is calibrated for miles, not kilometers, meaning the watch was originally made for the U.S. market. Estimate: $200,000–$400,000.
Steel Patek Philippe ref. 2508 (lot 44). Photographer: Stephen Pulvirent/Bloomberg Business
The ref. 2508 is a real connoisseur's watch, an oversize calatrava-style that displays only the time and has a waterproof case. The lines are elegant, but the dial has a sharp, modern look. This watch dates to 1957 and is only the 15th stainless steel 2508 known to exist. Estimate: $20,000–$40,000.
14k Gold Rolex Daytona ref. 6264 (lot 40). Photographer: Stephen Pulvirent/Bloomberg Business
It might seem counterintuitive, but this 14-carat gold Daytona is much rarer and thus more valuable than its 18k brothers. The case has a softer gold tone to it, and the bracelet is a stretchy, rivet-style Rolex bracelet that might be the coolest part of the watch. If you look at 12 o'clock, you'll see a Tiffany & Co. stamp in addition to the Rolex logo, meaning the watch was originally sold by the New York jeweler. Estimate: $80,000–$120,000.
Platinum Patek Philippe Manta Ray (lot 56). Photographer: Stephen Pulvirent/Bloomberg Business
The Manta Ray is a weird one. Officially the watch is called just the reference 2554, but even the hardest of hardcore collectors probably doesn't know that number. The watch has a dramatically sculpted case, with sharp edges and deep bevels that span the entire perimeter. This one's platinum and looks shockingly contemporary for a timepiece made in 1956. Estimate: $60,000–$90,000.
F.P. Journe Vagabondage II (lot 195). Photographer: Stephen Pulvirent/Bloomberg Business
The Vagabondage is an anomaly in F.P. Journe history. It uses a tonneau-shaped case instead of the usual round one, has a digital time display, and shows all the inner workings through a mostly transparent dial. Watching the minutes and hour change at once on this watch is incredible, as all three discs jump instantaneously. Less than 150 were made, so don't miss out. Estimate: $40,000–$60,000.
Patek Philippe ref. 2499 Third Series (lot 185). Photographer: Stephen Pulvirent/Bloomberg Business
The ref. 2499 is the direct descendent of the reference 1518 above, with a slightly more minimal dial and redefined profile. There are multiple series of 2499 since the watch was produced for 35 years, and collectors can get extremely particular about which one they're after. This is from the third series and dates to 1976. Even though the watch was made for such a long time, fewer than 10 left the Patek workshop most years, so these are rarer than you'd think. Estimate: $260,000–$360,000.
Svend Andersen Chrysler Building (lot 49). Photographer: Stephen Pulvirent/Bloomberg Business
OK, this is basically the opposite of most other watches here. Made by Danish watchmaker Svend Andersen in 1999, this has two displays, one hidden between the lugs at 6 o'clock so you can discretely read the time without moving your wrist. The massive guilloché depiction of New York City's Chrysler Building is less discrete but beautiful and certain to get the right kind of attention. Estimate: $10,000–$15,000.
Patek Philippe ref. 1436 Split Seconds Chronograph (lot 47). Photographer: Stephen Pulvirent/Bloomberg Business
Oh boy. Where to start with this one? It's a rare ref. 1436 chronograph that has a split-seconds mechanism activated by pushing the crown and a massive Tiffany & Co. stamp at 12 o'clock just above Patek Philippe. If you're a collector of midcentury chronographs, this is basically a perfect storm. Bidding on this one could easily go crazy and start creeping toward the $500,000 mark. Estimate: $150,000–$250,000.
Patek Philippe ref. 130 Chronograph (lot 45). Photographer: Stephen Pulvirent/Bloomberg Business
This watch has a lot in common with the ref. 1463 above: It's a classic midcentury chronograph, and it has a large Tiffany & Co. signature on the dial and an additional rare trait in the form of oversize chronograph registers. The side and back of the case are engraved for a Long Island yacht club, but everything else about the watch appears totally untouched. Estimate: $60,000–$80,000.
Rolex Submariner ref. 6538 "Big Crown" (lot 37). Photographer: Stephen Pulvirent/Bloomberg Business
Rolex Submariners don't get any better than this. The reference 6538 is the so-called James Bond watch sported by Sean Connery in the first film and is distinguished by the eponymous oversize crown, white seconds hand, and minimalist dial. This one also has four lines of text at the bottom of the dial (instead of the more common two), and the case is so sharp you could cut yourself. If you're a Rolex collector, this is your holy grail. Estimate: $60,000–$80,000.
Universal Genève Hermès Chronograph (lot 26). Photographer: Stephen Pulvirent/Bloomberg Business
Universal Genève might not be as famous as Patek, but in the early part of the 20th century, Hermès sold its watches alongside saddles and bags. This is the only known chronograph with the old-school script Hermès logo at 6 o'clock. Even without that, the three colors of printing on the dial are well maintained despite background patina. If you're looking for esoteric collector cred, you can't do much better. Estimate: $15,000–$25,000.
Vacheron Constantin King Alexander Chronograph (lot 81). Photographer: Stephen Pulvirent/Bloomberg Business
We can't finish without a royal watch: This 1927 monopusher (one-button) chronograph has a hard-fired enamel dial and was purchased by King Alexander I of Yugoslavia. It was likely a gift to a friend or dignitary and has the king's seal engraved on the back. The watch also comes with a 1963 letter from Vacheron Constantin confirming that the watch was originally sold to the king, so you're getting the real deal. Estimate: $40,000–$60,000.