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The 10 Most Expensive Cars Heading to Auction at Monterey Car Week

gray car in driveway
Monterey Car Week's Most Expensive Auction CarsRemi Dargegen ©2024 Courtesy of RM Sotheby's

The festivities surrounding the Pebble Beach Councours d'Elegance collectively known as Monterey Car Week bring together the perfect Venn diagrammatic overlap between two demographics: people who are obsessed with fancy vintage cars, and people who are extremely rich. So while most people attend the week's festivities to display / gawk at / take creepy cosplay selfies with some of the most gorgeous classic vehicles on Earth, MCW is also an irresistible marketplace for businesses peddling pricey items to autophiles.

There are sales events for a wide swath of items, including art, models, furniture, and even clothing — but the main attraction, and the biggest ticket one, are the events held by the major automotive auction houses. So prime is Pebble Beach as a site for the sale of top-tier vintage vehicles that, according to the valuation experts at Hagerty, fully half of the 30 most expensive cars ever to cross the block have traded hands in Monterey.

This year’s auction lineup — featuring lots from Gooding & Company, RM Sotheby’s, and Broad Arrow — promises to be particularly stellar, or at least pricey, with nearly all of our picks entering into the rarified eight-figure range (and nearly all of them, not surprisingly, being Ferraris.) So, scroll through our list, go buy your lottery tickets, and let us know in the comments which one of these 10 you'd buy if you hit the jackpot.

9. 1955 Ferrari 857 Sport Spider (Tie)

Gooding & Company

Estimate: $6,000,000 – $8,000,000

This handsome Scaglietti-designed racer — the last of four 857 Sport Spiders produced — crashed on one of its first outings in 1955, and was returned to Scaglietti for repair. There, the famed Italian carrozzeria added a distinctive fin behind the driver’s headrest.

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Originally fitted with a 3.4-liter, Lampredi-designed four-cylinder, in a quest for more tractable power, an owner in the late 50s replaced that engine with a Corvette V8. Carol Shelby and Jack McAfee drove the car to podium finishes in the 1960s, before it was sold to artist Andy Warhol, who painted the car yellow for a planned, but never filmed, movie. The original engine was reunited with the car during a 2011 restoration, which also corrected Warhol’s unfortunate color choice.

a red car parked on a road
Gooding & Company

9. 1995 Ferrari 333 SP Evoluzione (Tie)

Gooding & Company

Estimate: $6,000,000 – $8,000,000

This sophisticated, closed-body racer — one of just 40 built — was created by Ferrari in collaboration with Dallara to compete in IMSA races.

Equipped with a 650-hp 4.0-liter DOHC V12 coupled to a five-speed sequential manual gearbox, it was campaigned by teams from Scandia and Moretti, seeing six podium finishes in 1995 and seven in 1997. It was also the fastest qualifier, the 2nd in class, and 6th overall at the 1997 24 Hours of Le Mans. Driven in-period by Alboreto, Montermini, Moretti, Papis, Theys, and Vélez, it is one of only 9 Evoluzione models built during the 333 SP’s limited run.

red car on gray backdrop
Gooding & Company

8. 2002 Ferrari F2001b Formula 1

RM Sotheby’s

Estimate: $8,000,000 – $10,000,000

This chassis, #215, with its roaring Tipo 050 V-10 engine mated to a sequential seven-speed transmission, was driven to one win and two podiums by famed Ferrari F1 driver Michael Schumacher. This makes it one of only (only?) 30 Ferrari chassis to garner a certified Schumacher victory.

It also had the honor of scoring the 150th Ferrari F1 Pole Position start at the Malaysian Grand Prix that year. Many consider this purposeful yet curvaceous racer a pinnacle of Ferrari F1 design.

a red car parked on a road
RM Sotheby's

7. 1997 Porsche 911 GT1 Rennversion

Broad Arrow

Estimate: $8,500,000 – $10,500,000

One of only nine customer GT1s produced, this mid-engined modification of the rear-engined 993 Porsche 911 chassis was purchased for over $1 million in 1996 by Roock Racing, and competed in the 1997 24 Hours of Le Mans and the IMSA series.

Its 3.2-liter twin-turbocharged boxer-six made 600 hp, which seems like more than enough to catalyze a wreck, but this particular car has somehow never been severely damaged or rebuilt. It was raced by Allan McNish and Andy Pilgrim to an IMSA GTS-1 Class championship in 1997.

yellow car on a road
Broad Arrow Auctions

6. 1937 Bugatti Type 57SC Atalante

Gooding & Company

Estimate: $9,000,000 – $11,000,000

You know our list is elevated when a Bugatti Type 57SC Atalante —one of the most beautiful and collectible vehicles ever made— doesn't crack the top five. One of just 17 Atalantes produced, this particular example was the French/Italian/German marque’s show car at the Paris and London auto shows in 1937, and one of the last 57S Atalantes built.

It maintains its original chassis, coachwork, and engine, which was more than enough to help propel it to a First in Class win at Pebble last year. With a 200-hp supercharged 3.3-liter DOHC straight-eight engine, and blue-over-Havana color scheme, we think we would look good driving this around Manhattan.

blue car parked
Gooding & Company

5. 1957 Ferrari 625 TRC Spider by Scaglietti

RM Sotheby’s Lot #248

Estimate: $9,000,000 – $11,000,000

One of the loveliest of late-1950s Ferrari designs (and late '50s cars in general) this Testa Rossa was originally owned by John von Neumann, one of the founders of the California Sports Car Club and a salesman at Rober Barlow’s International Motors — the dealer that later helped convince Ferrari to develop the contemporary 250 California Spider for the American market. (Foreshadowing!)

Newman asked the factory for an upgrade, ditching the 500 TRC engine for an updated Tipo 625 four-cylinder and giving the car a 45-hp boost, to 225. While the original engine is included in the sale, this car is currently running a 3.0-liter Colombo short block that provides a terrifying 322 hp. This car had 21 podium finishes in its period.

red car parked on a road
RM Sotheby's

4. 1955 Ferrari 410 Sport Spider by Scaglietti

RM Sotheby’s Lot #357

Estimate: > $15,000,000

This one-of-one Speciale was the prototype for the 410 Scuderia Ferrari Works cars. It was developed in the process of creating a racing chassis for a doomed, never-run, five-day pan-Mexican rally, the 1955 Carrera Panamericana.

Instead of using the existing V-12 race engine from preceding cars, Lampredi chose to equip it with the 410 Superamerica’s big 4.7-liter V-12, which it still retains. This particular car was driven by Carroll Shelby to a winning finish in the 1956 Palm Springs Road Races. It was restored in 2017 before being shown at Pebble in 2018.

red car parked on driveway
Theodore W. Pieper ©2024 Courtesy of RM Sotheby's

3. 1961 Ferrari 250 GT SWB California Spider

Gooding & Company

Estimate: $15,000,000 – $17,000,000

As mentioned previously, the 250 GT SWB California Spider was designed to appeal to the growing American market, with a more sophisticated chassis, four-wheel disc brakes, and a more robust motor than its predecessor. Though variants of the 250 preceded and followed it over a 12-year period, only 56 250 GT SWB California Spiders were produced, and only 37 of those had factory covered headlamps. This is one of those models.

Featuring its original, numbers-matching, 240-hp 3.0-liter SOHC Tipo 168/61 V-12 engine, it has been sadly downgraded (in our opinion) from its original dark blue-over-red livery to a more basic red-over-black.

red car parked on beach
Gooding & Company

2. 1960 Ferrari 250 GT SWB California Spider by Scaglietti

RM Sotheby’s Lot #346

Estimate: $16,000,000 – $18,000,000

Did you get outbid on the 1961 250 GT SWB Covered Headlamp California Spider we just showed you? Well, lucky you: we have another one. Actually, the Ur-version, the first one ever built — and the one Ferrari used to show off its new model at the 1960 Geneva Auto Show.

This one blessedly maintains its original non-red color, as well as its original engine, transmission, and bodywork. It has never been offered for sale before publicly, and we predict that it will sell for above its estimate.

gray car parked in driveway
Remi Dargegen ©2024 Courtesy of RM Sotheby's

1. 1938 Alfa Romeo 8C 2900B Lungo Spider

Gooding & Company

Estimate: $16,000,000 – $20,000,000

Alfa’s 8C cars are among the most iconic and successful sports cars of the pre-WWII era, and this model — the 2900 B Lungo (long chassis) Touring Spider — is perhaps the most desirable configuration.

2900s won the last three Mille Miglias prior to WWII and the first post-war running in 1947, thus cementing their primacy. Equipped with a twin-supercharged 2.9-liter straight-eight engine and twin Weber carbs, they put out 180 hp. The elegant, streamlined Carrozzeria Touring Superleggera (lightweight) bodywork seen here allowed drivers to make the most of that potent power-plant.

This example was delivered to Egypt when new for a “diplomat,” though given Italy’s incursions into North Africa during that time, we might not be such a fan of their politics. More recently, it won Best of Show at Villa d’Este in 1996 and First in Class at Pebble in 2000. More intriguingly, it was stolen in 2022 while being transported to Maine for restoration, and the insurer, AIG, paid out $23 million on the claim. As the car’s current owner, it repaired the superficial damage it endured and is now looking to recoup its loss. We’ll see where it lands... but it won't be cheap.

black car parked on a road
Gooding & Company

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