Excellent Vintage and Pre-Owned Watches Under $5,000

Excellent Vintage and Pre-Owned Watches Under $5,000

| 09.04.23

Previously on Transmissions, we explored great vintage and pre-owned watch options under $2,000. While there are excellent timepieces to be had in this price category, upping the ante and increasing one’s budget to $5,000 yields some of the most value-laden watches in the entire industry. It’s truly mind-boggling what you can get on your wrist for 50 Benjamins (or less) — including in-house movements, precious metals, special features, and more. 

While you may think that a relatively low price threshold would yield mostly simple, time-only watches, there are a surprising number of chronographs, dress watches, GMTs, and other complicated fare available for your perusal. Join us as we explore some of the best from brands like Tudor, IWC, Movado, and more in this week’s deep dive into some of the best vintage and pre-owned watches under $5K!

Vulcain Cricket ($2,250)

Vulcain Cricket - IN THE SHOP

The Vulcain Cricket, watch of presidents, is the best known example of the mechanical alarm watch — at a user-appointed hour, it will audibly chirp and vibrate, providing a form of haptic feedback that long predates any product from Apple. This example from the 1960s is notable for its large 38mm case and handsome, multi-tone dial. Featuring applied, gold-toned indices, a matching ‘dauphine’ handset, an outer alarm-setting track, and a fourth, red-tipped alarm hand, it’s powered by the hand-wound Vulcain Calibre 120 movement and comes paired to a brown Old Fashioned Alligator leather strap from Analog:Shift. If you’re looking to ditch your phone for some old-fashioned, mechanical fun, this is the watch to do it with!

Hamilton Super Compressor 600 Diver ($2,300)

Hamilton Super Compressor 600 Diver - IN THE SHOP

The ‘Super Compressor’ case was a fascinating horological development. Designed to increase in water resistance the deeper it dove — water pressure would “sandwich” it together — it was, ultimately, less effective than a simple screw-down crown, screw-down caseback, and effective gaskets. But boy, did it power some beautiful watches — including this Hamilton. Equipped with the dual, crosshatched crowns found on Super Compressor cases (one to control the movement, and one to control the internal dive bezel), it features a handsome, silver-tone dial with lumed, applied indices, a highly lumed ‘baton’ handset, and the Hamilton Caliber 600 (ETA 2452) automatic movement. Plus, it’s fitted with a correct stainless steel bracelet from J.B. Champion with a signed blade clasp.

Longines Ultra-Chron ($2,500)

Longines Ultra-Chron - IN THE SHOP

The Ultra-Chron was but the latest in a long line of high-frequency watch movements developed by Longines. Upon its debut in 1967, its 36,000-vph beat rate allowed the St. Imier-based brand to compete in the ongoing battle for accuracy between all manner of Swiss, Japanese, and other brands — a competition that continues today. Housed in a 37mm stainless steel case with a handsome, black ‘quadrant’ dial, a date window at 3 o’clock, and beautiful applied, faceted indices, it’s paired to a steel mesh bracelet with a signed, locking clasp. Perfect for both men and women given its dimensions, it’s a vestige of a time when restrained, elegant industrial design was the norm, rather than the exception, in watchmaking.

Memosail Regatta Yacht Timer 'UFO' Chronograph ($2,950)

Memosail Regatta Yacht Timer 'UFO' Chronograph - IN THE SHOP

Memosail’s regatta timers are some of the coolest in the category, with this particular reference being a standout for its odd case shape, colorful livery, and highly esoteric complication. Housed in a 45.5mm stainless steel ‘UFO’ case, it features a blue dial with a unique regatta timer: Depress the top chronograph pusher, and colored disc displaying minutes 10-6 begins counting down. It then switched over to minutes 5-1, after which the countdown is over, and each vessel must cross the regatta’s starting line. Wildly neat (even if you don’t sail in regattas), it comes with its inner box and ships with a correct, signed blue rubber strap.

Tudor Black Bay Fifty-Eight Blue ($3,200)

Tudor Black Bay Fifty-Eight Blue - IN THE SHOP

We’re gonna go out on a limb here and claim that, for the money, there’s simply no better modern dive watch available than Tudor's Black Bay Fifty-Eight. (There, we said it — come at us!) Housed in a most excellently sized 39mm case and powered by Tudor’s in-house Calibre MT5400 movement, it features a unidirectional dive bezel with a blue insert, a matching blue dial with the brand’s classic ‘snowflake’ handset, an oversized, signed winding crown, a sapphire crystal, and a matching, stainless steel ‘rivet’-style bracelet with a signed clasp and diver’s extension. Show us another example of a vintage-inspired watch with this much charm, robustness, and beauty, and we’ll eat our hat.

IWC Pilot’s Chronograph Spitfire ($3,500)

IWC Pilot's Chronograph 'Spitfire' - IN THE SHOP

The fact that one can buy into IWC’s long history of pilot’s watch manufacturing for less than the cost of a month’s rent in a major American city has to be one of the great horological coups of the 2020s. We’re talking about a 43mm stainless steel chronograph powered by the brand’s (Valjoux 7750-based) Calibre 79320 chronograph movement and paired to a matching, stainless steel bracelet — what could possibly be more iconic? Outfitted with a handsome sunburst grey dial from the ‘Spitfire’ collection with a triple-register chronograph display, day-date windows, and a highly legible, lumed, white ‘sword’ handset, this timepiece simply oozes aeronautical cool. 

Cartier Santos Dumont Small ($3,800)

Cartier Santos Dumont Small - IN THE SHOP

Simply a stunningly handsome creation, the Santos Dumont has been a dress watch staple since the early 20th century — and this despite the fact that technically, it was created as a pilot’s watch. (And the world’s first, at that!) Though it’s available in several sizes and iterations, the Small stainless steel variant measuring 27.5mm in diameter is perfect for both men and women. Powered by a quartz movement and paired to a signed, navy blue alligator leather strap, it features all the things that make a Cartier a Cartier: a blue cabochon crown, Roman indices, a thin, blued steel sword handset, and a dozen other small touches that lend an air of grace, formality, and elegance. 

Franck Muller Conquistador Chronograph ($4,200)

Frank Muller Conquistador Chronograph - IN THE SHOP

Looking for a chronograph but prefer a more contemporary, avant garde option? Look no further than the Conquistador from Franck Muller. Dating to the 2000s and housed in a 35mm stainless steel case with a matching bracelet, it features the brand’s signature dial with highly stylized Arabic indices, a dual-register chronograph layout, a date window at 6 o’clock, an outer minute track in red and black, and a lumed, blued steel ‘leaf’ handset. Powered by Franck Muller's Calibre 1185 SC automatic movement, it’s a distinct fusion of modernist design and a useful complication that can be worn day to day. (Extra points will be awarded for pulling this one off with a tuxedo, however.) 

Sinn 140/142 Chronograph ($4,800)

Sinn 140/42 Chronograph - IN THE SHOP

A complicated tool watch with a space-related history — a variant was worn by German astronaut Reinhard Furrer during the Spacelab D1 mission on the Challenger in 1985, one year before its final, fateful mission in 1986 — the Sinn Reference 140/142 is an automatic chronograph packed with useful features. Powered by the venerable Lemania 5100, it features a triple-register chronograph with a 12-hour counter and central chronograph minutes, a day-date display, and a 24-hour counter at 12 o’clock. (Plus, a secondary crown at 10 o’clock controls an internal, rotating count-up bezel — another incredibly handy feature.) Paired to a matching, brushed stainless steel bracelet, this excellent tool is emblematic of German industrial engineering. 

Universal Genève Uni-Compax ($4,900)

Universal Genève Uni-Compax - IN THE SHOP

Betcha didn’t think you could nab a solid-gold chronograph from one of the most prestigious marques in the vintage watch world for under $5K? Not only is it possible, but this particular example, housed in a svelte, 34.5mm case, is from the 1940s, lending it an air of historical interest that predates the explosion in tool watches in the 1960s. With its sparse, dual-register chronograph layout on a silver dial, this Uni-Compax from Universal Genève is an elegant masterpiece; rectangular pushers, an acrylic crystal, an outer tachymeter scale, and a matching, blued-steel handset powered by the hand-wound Calibre 285 movement make it a winner in the eyes of vintage watch collectors. Combine it with the included Analog:Shift Blue Cervo leather strap with a gold-plated pin buckle, and you’re off to the races.