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“Vintage Rolex is my focus,” Timothy Yong said. “I track every auction.”

Mr. Yong, 33, has five rows of timepieces in a glass display case spanning one wall of an upstairs room in his home here. Also filling the space: shelves of vintage whiskeys, neatly stacked boxes of shoes and two long racks of business suits.

“This case is for watches I wear daily,” said Mr. Yong, a Citigroup executive, noting that he keeps his most prized watches in a bank vault.

While declining to be specific, Mr. Yong said that at one time he owned several dozen watches; now he has honed his collection to half as many. Nor will he estimate the collection’s value. “Vintage collecting is what one person is willing to pay another — it’s not a market,” he said.

But is the collection a lucrative investment? “Do I look at watches as a way to make money?” Mr. Yong said. “Absolutely not. Watches are very illiquid. You can’t sell them the next day.”

One piece in his collection is a Rolex Stella Dial Day-Date from the 1970s, its aqua dial offset by a mauve-colored alligator-skin strap. Mr. Yong bought it from another collector to begin a Stella sub-collection.

“I really like the Stellas and wear them a lot,” he said, noting that their solid enamel dials are quite delicate. The model also has dials in ultramarine blue, Kelly green and a tangerine orange, and Mr. Yong hopes to acquire all of them.

“Many for sale have swapped parts,” Mr. Yong said. “It’s very hard to find originals that are not cracked. I’m taking my time to find really nice ones.”

The youngest of three sons, Mr. Yong caught his brothers’ collecting bug as a boy, first receiving a TAG Heuer from his mother and then, at age 16, a Zenith El Primero from a brother.

He started collecting vintage watches from flea markets during his studies at New York University. “With vintage, I could buy great brands on a budget,” he said. Picking up his Patek Philippe Calatrava, he noted that the older model cost a fraction of the nearly $20,000 price for a very similar modern one.

He also added that vintage watches often have 34-millimeter cases that particularly suit his small wrists.

But isn’t it easy to make mistakes when buying on the secondary market? “Have I gotten burned?” Mr. Yong said. “One hundred percent.”

He recalled the time he bought a secondhand Rolex with a fake dial. “I tried to get a refund,” he said, “but the dealer said it was a consignment where he earned a commission and couldn’t do anything — caveat emptor.”

On his wrist this particular day, the timepiece he wears most often and calls his “best value” watch: a white gold Patek Philippe 3940G Perpetual Calendar, purchased for $30,000 — before Patek replaced it with the 5140, which Mr. Yong said is one millimeter larger and retails for close to three times the price.

Now considered the family watch expert, he credits much of his knowledge to the Vintage Rolex Asylum, known to its members as V.R.A. It was founded in 2013 by serious collectors in Jakarta, Indonesia, and is now one of the world’s largest vintage Rolex collectors’ clubs. Mr. Yong said he enjoyed the annual gatherings — in Bali, Hong Kong, Jakarta — and keeps up with members closely through social media.

Of some 60 members, he said, most are Chinese-Indonesian men living in Asia, though the club has members from the United States and Europe. And, he noted, “one or two women.”

“I think the large growth of vintage is driven by social media, and the growing quality of content online,” he said, noting that, for example, he often consults with club members, using WhatsApp, to verify serial numbers before buying a new timepiece.

Club members living nearby, or traveling through Singapore, regularly meet for they call GTGs (short for “get-togethers”). Because the city-state is relatively crime-free, he said, members gather in neighborhood cafes and have few qualms about bringing along several watches for a show-and-tell. But even as members are generous about sharing knowledge with one another, most decline to talk about their collections with strangers for security reasons.

An overseas dealer recently sold Mr. Yong his two favorite timepieces: a white-faced Rolex Daytona 6262, and a black-faced 6239. (The Daytona often is called “the Paul Newman” because the actor was known to wear it after he took up auto racing in the 1970s.)

But, unlike other Daytonas, Mr. Yong’s watches have distinctive block markers and cross hairs on the sub-dials.

As the father of two sons, a 2-year-old and a newborn, Mr. Yong said he will “leave one for each son” eventually.

“I was lucky to find two in this condition,” he said. “I’ve been looking for them for the past two years.”