These are the 3 classic cars everybody will be talking about at Pebble Beach

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The 1962 Shelby Cobra CSX 2000.

There's an outstanding selection of vintage cars going up for sale at the Pebble Beach auctions this weekend.

The five-day event in Monterey, Calif. kicked off Wednesday and left ample time for car fanatics to check out the selection before the bidding begins this weekend. The five different auctions are expected to bring in a grand total of $370 million, McKeel Hagerty, the CEO of Hagerty, the largest insurer of collector vehicles, told Business Insider.

While that estimate sounds like a lot, it's actually down 7% from last year, Hagerty said.

"This is the first year in a number of years where an awful lot of people are more cautious," Hagerty said.

Hagerty said that caution stems from Brexit and the devaluation of the pound, but that the car market is also generally more cautious in an election year because "people just don't know what the world is going to look like a few months from now," he said.

Despite these headwinds, Hagerty said the car market as a whole is strong.

"There's no one suggesting a bubble is bursting - it's just a more cautionary tone," he said.

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The 1962 Ferrari 268SP is the third of the six of its kind ever built.

The cars that typically sell for the most are European sport cars from the 1950s and 1960s, Hagerty said.

"Typically if you look at last five years of top 10 selling cars, Ferraris from the 1950s and 1960s would absolutely carry the day," Hagerty said.

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The 1955 Jaguar D-Type.

But for the first time ever, a Ferrari is not expected to be the number one selling car, Hagerty said. That spot is reserved for the 1955 Jaguar D-Type, which won the 24 Hours of Le Mans in 1956. It could sell for as much as $25 million.

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The 1962 Shelby Cobra CSX 2000.

The 1962 Shelby Cobra CSX 2000 is also expected to be a top seller. It's the very first Shelby Cobra ever made, and is regarded as one of, if not the most, important sports cars in history.

Hagerty said he predicts the Shelby Cobra could also go for as high as $25 million.

Other than that, Hagerty said it will be interesting to see how modern supercars perform at the auctions.

"We're really watching these sort of vehicles, the cars that represent the change," Hagerty said. "Are they going to be bought from younger collectors? Who are the people buying them? We'll be watching."