When we first started keeping our listings of the most valuable cars and motorcycles sold at auction, a $3 million sale would land a spot in the top 100 most valuable cars ever sold at auction. Nowadays, a $5-million sale won’t get you into the top 100, but it still puts you into the top 150 most valuable cars of all time, so that’s where we’ve drawn the line in our preview of the coming Monterey Car Week Auction cluster.

Over the next fortnight, we’ll preview the most valuable and the most interesting cars going to auction in Monterey in 2021, plus we’ll include some of the private sale cars that will also be on offer in Monterey.

1930 Bucciali Tav 30 La Marie Torpédo Sport Type Cannes

Bonhams

Estimate: Refer to department for estimate
Bonhams | Lot 73 | 13-August-2021
Detailed Description and images
We’ve included this car in the $5 million plus category because it has the potential to be there given of its rarity, subsequent influence and historical significance. This is the only one.

1953 Ferrari 166 MM Spider Series II

RM-Sotheby’s / Theodore W. Pieper

Estimate: $4,000,000 – $5,000,000
RM-Sotheby’s | Lot 352 | 14-August-2021
Detailed Description and images
This significant V-12 Ferrari competition spider has been racing for nearly 70 years, minus a holiday here and there for restoration purposes, plus a seven year period during which it was stolen and dropped off the map. It’s a genuine Ferrari competition machine, the fourth of six Vignale Spiders built on the second-series 166 MM; and the tenth of 13 overall examples. In period, it participated in the 1954 Mille Miglia and its history is well documented in a lengthy report by Ferrari historian Marcel Massini. It received a comprehensive restoration by marque specialist DK Engineering that was completed in 2009, and it was the recipient of a Ferrari Classiche White Book in 2016, affirming its historical significance.

1959 Aston Martin DB4GT Lightweight

RM-Sotheby’s / Rasy Ran

Estimate: $4,000,000 – $5,000,000
RM-Sotheby’s | Lot 113 | 12-August-2021
Detailed Description and images
In its day, the Aston Martin DB4 GT was the fastest road car in the world, but with the Ferrari 250 GT SWB as its major foe in sports car racing, something more was needed. The DB4 GT is a rare car in its own right, with just 75 cars produced (30 in left-hand-drive, 45 in RHD), but Aston Martin’s development chief John Wyer (who would go on to produce the Ford GT40 and Porsche 917K) decided a lightweight version was in order and nine were produced for competition purposes. This is one of them. It was sent to America brand new to compete in the 12 Hours of Sebring, but was delayed in customs until the day after the race, hence living its entire life unmolested by the brutalities of racing.

As there are only nine, and closely held, they almost never come up at auction, which is why this car (DB4GT/0168/L) is likely to become one of the most valuable cars ever sold at auction. The last Lightweight to grace the auction block was DB4GT/0169/L, which sold at Bonhams’ Bond Street Sale in December 2019 for £2,367,000 (US$3,108,344).

1952 Ferrari 340 America

Mecum

Estimate: $4,800,000 – $5,300,000
Mecum | Lot F74 | 13-August-2021
Detailed Description and images
Beautifully restored and certified by Ferrari Classiche with full factory documentation, this car is a piece of living motorsports history in every possible respect, retaining its original chassis and engine.

It is one of just 24 Ferrari 340 Americas built, and finished second in class and fifth overall at the 1952 24 Hours of Le Mans. Very similar cars won the 1951 Mille Miglia and finished third and fifth in the 1952 Carrera Panamericana, just minutes behind the all-conquering Mercedes-Benz 300 SL after 19 hours of racing at ballistic speeds in what will go down in history as the world’s fastest and most dangerous motor race – hence this car was at the very forefront of automotive performance in its day. It is presented at auction finished in period-correct French Racing Blue livery and the race No. 14 that graced the car during its Le Mans effort. The car was restored to perfection and made its post-restoration debut at the Ferrari North America display held at the 2019 Pebble Beach Concours d’Elegance.

It is certified by Ferrari Classiche, the “Red Book” accompanying 0202A bears a white stripe, signifying this 340 America’s exceptional status as a significant competition Ferrari. Another book with the vehicle contains a wealth of additional documentation, including period photographs, news clippings, race results and extensive pre-restoration and restoration photographs.

1958 Ferrari 250 GT Series I Cabriolet

Brian Henniker / Gooding & Co

Estimate: $4,500,000 – $5,500,000
Gooding & Co | Lot 137 | 15-August-2021
Detailed Description and images
The Series I Pinin Farina Cabriolets are generally regarded as one of the great masterpieces of Italian automotive. Just 40 Series I cars were built, and this car was originally finished in “Oro Andalusia” as the 34th of the series and it became the centerpiece of the Ferrari display at the 1958 Earls Court Motor Show.

The car was sent to Wayne Obry’s Motion Products, where it was given a 19-month, 9,000-hour restoration which resulted in it achieving many First-in-Class and Platinum Awards at Concours events across the nation. Some of the awards this car has won are truly remarkable, with wins at the Cavallino Classic, Amelia Island Concours d’Elegance, Concorso d’Eleganza Villa d’Este and a perfect 100-point score to win its class at the Pebble Beach Concours d’Elegance.

This car has its original chassis, body, engine and gearbox, it is Ferrari Classiche Certified and is offered for sale with Massini Report, Books, Tool Roll, and Extensive Documentation File.

The last Series I Cabriolet to reach auction fetched $6,800,000 at Gooding & Company’s Pebble Beach auction in 2019, with the previous sales being €4,719,000 at RM Sotheby’s Ferrari Leggenda e Passione auction at Maranello in September 2017, $4,840,000 by Gooding & Co at Pebble Beach in August 2017, $5,720,000 at RM Sotheby’s  Driven by Disruption sale in December 2015, $5,610,000 by Gooding & Co at Pebble Beach 2014, and $6,820,000 at Bonhams Quail Lodge Auction in August, 2014. Quite clearly, given those results and the unquestioned quality, this car could easily blow past its upper estimate.

1968 Porsche 911 R

RM-Sotheby’s / Robin Adams

Estimate: $4,500,000 – $5,500,000
RM-Sotheby’s | Lot 339 | 14-August-2021
Detailed Description and images
One of just 20 serially built 911 “R” lightweights, the lightest production-based Porsche 911 ever built.

Raced and rallied extensively in-period, this extremely rare Porsche is presented in its 1967 Tour de Corse livery, with its numbers-matching magnesium-cased engine. Restored by marque experts with careful attention to authenticity and detail, using NOS parts throughout.

1983 Porsche 956 Group C

RM-Sotheby’s / Matthew Howell

Estimate: $4,500,000 – $6,000,000
RM-Sotheby’s | Lot 342 | 14-August-2021
Detailed Description and images
If you weren’t paying attention to sports car racing in the 1980s, it is the period where Porsche went from being a revered name to one that was so dominant that it almost defied belief. The Porsche 956/962 dynasty won the first and the last 24 Hours of Le Mans in which they were entered, twelve years apart and completely dominated the sport on such a level that the (equally legendary) Porsche advertising department was able to make its most famous poster in 1983 … the year the auction car was produced.

RM-Sotheby’s / Matthew Howell

This Porsche 956 started at Le Mans in both 1983 and 1984 and was running in third in 1983 when a fuel pump failure caused it to drop out. It also failed to finish in 1984 but its racing career included wins in the 1983 Brands Hatch 1000 KM and 1983 Can-Am Road America, it was the only 956 to win on American soil in-period and it is one of just two privateer-delivered 956 to beat the dominant Rothmans Porsche factory team 956s.

Very few Porsche 956s have been to auction and of those that have reached such public sale, Gooding & Co fetched the most, selling the 1983 Le-Mans-winning 956 for $10,120,000 at Pebble Beach in 2015. RM-Sotheby’s sold one of the ten factory-team examples from 1982 sold at Retromobile in 2014 for €2,352,000 and the car being offered at auction in Monterey went to auction once before in 2018 with expectations of between $5,250,000 and $6,750,000 but failed to sell.

According to RM-Sotheby’s, it is “the most original surviving example of the nine WEC privateer 956s.”

The final paragraph of the auction description says it all: “Today, 956-110 is offered in its full 1983 Le Mans bodywork with JDavid livery. Supplied with extensive documentation, and featured prominently in Ultimate John Fitzpatrick Group C Porsches: The Definitive History by Mark Cole, this wonderful veteran of Porsche’s hugely successful foray into ground-effects prototype racing is ready for concours or museum display; for someone willing to again explore its phenomenal capabilities, 956-110 could be prepared for a return to racing, as any vintage event would be thrilled to have it lined up on the grid.”

1936 Delahaye Type 135 Competition Court Teardrop Coupe

Mecum Auctions

Estimate: $5,000,000 – $6,000,000
Mecum | Lot S95 | 14-August-2021
Detailed Description and images
Figoni et Falaschi’s “Goutte D’Eau” style coupes are among the most beautiful cars ever created and this completed car with its exquisite coachwork was delivered new to the Delahaye factory and retained there as a demonstrator. It was blessed with the “Competition Court” chassis and engine, meaning it was the highest specification of car available – just 30 such chassis-engine combinations were created and they weren’t even listed in the official Delahaye catalogue.

The 24 Hours of Le Mans was cancelled in 1936 due to a workers strike in France, but in the 1937 event, two Delahaye 135CS finished second and third behind the famous Bugatti 57G Tank and a 135CS also won the Monte Carlo Rally. In 1938, the Delahaye 135CS first, second and fourth in the world’s most important race, meaning that this art deco masterpiece is a lot more than just a pretty face.

Mecum Auctions

Though this car was restored 20 years ago, it is still in splendorous condition, as one would expect. When it made its debut from restoration in 200, it was awarded First in Class at the 2001 Pebble Beach Concours d’Elegance.

1958 Ferrari 250 GT LWB Berlinetta ‘Tour de France’

Courtney Frisk / RM-Sotheby’s

Estimate: $5,750,000 – $6,500,000
RM-Sotheby’s | Lot 331 | 14-August-2021
Detailed Description and images
The 52nd of 72 alloy-bodied ‘Tour de France’ Berlinettas built, this car was originally owned by French industrialist and gentleman racer Jacques Peron. It finished fourth outright in the 1958 Tour de France and has subsequently been meticulously restored to exacting standards, with a mechanical restoration by Patrick Ottis.

The car was debuted at the 2016 Pebble Beach Concours d’Elegance, completing the Tour d’Elegance and being judged third in Class amidst very strong competition. It has been only selectively driven since and exhibited only once more at Pebble Beach, this time at Casa Ferrari as part of the concours celebrations in 2019.

Accompanied by the considerable trove of documentation and meticulous maintenance records kept since the 1970s, as well as copies of the correspondence between its original owner and Ferrari, this is almost certainly among the finest Berlinettas “Tour de France” to be found—a car of unimpeachable quality, provenance, and distinction.

The last few ‘Tour de France’ Berlinettas sold all indicate that the price estimate is accurate: $5,100,000 at Gooding & Co’s 2019 Pebble Beach Auctions; $5,890,000 at Gooding & Co’s 2019 Scottsdale Auctions; $6,600,000 at Gooding & Co’s 2018 Pebble Beach Auction; and $5,720,000 at RM-Sotheby’s 2016 Monterey Auctions.

1955 Jaguar D-Type

RM-Sotheby’s / Rasy Ran

Estimate: $5,500,000 – $7,000,000
RM-Sotheby’s | Lot 110 | 12-August-2021
Detailed Description and images
The market for D-Type Jaguars has been a bit chaotic in recent times, mainly due to Jaguar producing 25 continuation models at $1,500,000 each in 2018. With the exception of the $21,780,000 sale of the winning Ecurie Ecosse D-Type from the 1956 24 Hours of Le Mans, the only D-Types sold in the last six years were a 1955 Jaguar D-Type that fetched $6,000,000 in Scottsdale earlier this year, and the only continuation model to yet reach auction which fetched $1,325,000 at RM-Sotheby’s Elkhart Collection sale in October, 2020.

The continuation model sold with just 170 miles on the odometer, which cost the owner $175,000 plus auction fees and other ancillaries, so understandably, they’ve not popped up again at auction since.

The arrival of the continuation models didn’t do the existing stock of D-Types much good either, as the last D-Type to sell prior to the aforementioned was at Amelia Island in March 2015 for $3,625,000.

In between times, four D-Types went to auction with varying estimates of €5,900,000 to €6,400,000 in Paris in 2020, $10,000,000 to $12,000,000 in Scottsdale in 2018, $12,000,000 to $15,000,000 in Scottsdale in 2018 and AU$7,000,000 to AU$8,000,000 in Melbourne Australia in 2017.

The market is obviously treating the continuation models as different vehicles, and D-Type prices are hence due for some growth and stability, so it might not be a bad time to buy.

1959 Ferrari 410 Superamerica Coupe Series III

Darin Schnabel / RM-Sotheby’s

Estimate: $6,000,000 – $8,000,000
RM-Sotheby’s | Lot 337 | 14-August-2021
Detailed Description and images
This car has been to auction before, offering an eye-opening insight into to world of elite automobile collecting. After 20 years in a private collection, it went on the market with RM-Sotheby’s at Monterey in 2017, where it fetched $5,335,000. The new owner then went to Rob Meyers’ RM Auto Restoration for a comprehensive restoration. All mechanical systems were rebuilt as needed, though the engine was deemed to not require a complete teardown, and was therefore sympathetically freshened as needed. In a testament to the car’s originality, the Pinin Farina body numbers were found stamped on the expected locations including the bumpers, trim pieces and elsewhere on the body. Cosmetically, the car was returned to its original factory color scheme, with a fresh coat of Nero Tropicale paint and a new Naturale leather interior.

The 410 Superamerica was subsequently presented at the 2020 Amelia Island Concours d’Elegance, where it received a Best in Class Award. Subsequently the car was shown at the 2021 Cavallino Classic where it received a Platinum Award as well as the Robert Tallgren Memorial Elegance Cup, for the finest coach-built Ferrari and the Honorary Judges’ Cup, for the finest judged Ferrari selected by the Honorary Judges.

Retaining its numbers-matching engine, gearbox, and rear axle, this striking luxury Ferrari recently received its Ferrari Classiche certification and corresponding Red Book, a testament to its authenticity. As one of very few Series III cars built, 1305 SA offers rarity and assures a high degree of quality, being owned by some of the enthusiast niche’s most passionate collectors. It would make a stunning addition to any collection, particularly suited for connoisseurs of apex-level limited-series luxury grand tourers.

1966 Ford GT40 Alan Mann Lightweight

Josh Hway / Gooding & Company

Estimate: $7,000,000 – $9,000,000
Gooding & Co | Lot 39 | 14-August-2021
Detailed Description and images
The words “Never before offered for public sale” are rare in the collectible automobile world, particularly when a car is in or near the eight figure bracket because it is almost certain to be a potential “best in show.” There’s nothing quite like a car that hasn’t done the show circuit. This car fits the bill and more as it is a rare derivative of a rare and historically significant racing car: it is the first of two aluminum-bodied lightweight GT40s built in-period by Alan Mann Racing and it is the lightest GT40 ever built at 216 lb (980 kg).

Ford’s decision to halt further development of the Alan Mann Lightweights rendered them the rarest of all GT40s. With just two examples built, they are far more exclusive than any of the Mk I–Mk IVs, prototypes, and roadster models.

1962 Ferrari 268 SP

Patrick Ernzen / RM Sotheby’s

Estimate: $8,000,000 – $10,000,000
RM-Sotheby’s | Lot 234 | 13-August-2021
Detailed Description and images
This 286 SP claims extreme rarity in the Ferrari lineage as one of just six SP racers originally built and one of only two examples originally equipped with the developmental Maranello eight-cylinder engine. Boasting associations with legendary drivers like Lorenzo Bandini, Harry Heuer, Olivier Gendebien, and Ricardo Rodriguez, chassis 0798 was an integral part of Ferrari’s sports prototype development and racing campaign, and it laid the foundational groundwork for the famed Ferrari P cars. It is also no doubt a cornerstone of the 1964 SCCA D Modified Championship. As such, 0798 has been extensively chronicled and photographed in numerous books and articles, including significant coverage in John Godfrey’s authoritative 1990 volume Ferrari Dino SPs as well as a multi-part feature in Cavallino.

1966 Ferrari 275 GTB Competizione

RM-Sotheby’s / Robin Adams

Estimate: $8,000,000 – $10,000,000
RM-Sotheby’s | Lot 238 | 13-August-2021
Detailed Description and images
One of only 12 GTB/Cs built, this car won its class in the 1967 24 Hours of Le Mans, the 1000 Km de Spa Francorchamps and the 500Kms de Imola, becoming one of the most successful and pedigreed examples of the twelve 275 GTB/Cs. It last sold at auction at Bonhams Scottsdale sale in 2015 when it fetched $9,405,000.

Only two other GTB/Cs have been to auction since then, with one fetching $14,520,000 at Gooding & Company’s Pebble Beach auction in 2017 and another failing to sell against a $12,000,000 to $14,000,000 estimate at Gooding & Company’s 2018 Pebble Beach Auction. Based on those numbers, it looks set to become an eight-figure car.

1998 Mercedes-Benz AMG CLK GTR Strassenversion

Josh Hway / Gooding & Co

Estimate: $8,500,000 – $10,000,000
Gooding & Co | Lot 50 | 14-August-2021
Detailed Description and images
Built for racing homologation purposes, the racing version of this car won every round of the 1998 FIA GT series, and this registrable, road-going version offers a 600 horsepower, 6.9 liter fuel-injected V-12 engine, 6-Speed Xtrac Sequential Transaxle, superb handling, 4-wheel ventilated ceramic composite discs … and it’s unlikely you’ll ever drive it because it will depreciate so dramatically if you do drive it. Currently, it has just 1422 km on the odometer, the same mileage it had when it fetched $4,515,000 at RM-Sotheby’s in Monterey three years ago. Only a few of these cars have ever gone to auction with unsolds at Bonhams Les Grandes Marques du Monde in Paris in 2016, and Mecum in Monterey in 2013 (high bid $1,300,000). The only prior sale at auction other than the 2018 sale of this car, was at the Goodwood Festival of Speed in 2015 when an even rarer roadster sold for £1,513,500.

1959 Ferrari 250 GT LWB California Spider Competizione

Brian Henniker / Gooding & Co

Estimate: $10,000,000 – $12,000,000
Gooding & Co | Lot 36 | 14-August-2021
Detailed Description and images
Just 50 LWB California Spiders were built between 1957 and 1960, powered by a 2,953 cc SOHC 60 degree Colombo V12 engine producing 237 hp (177 kW) at 7,000 rpm. Of those, it is thought that around 10 were originally supplied with a combination of competition features, including tuned engines, ribbed-alloy gearboxes, limited-slip differentials, long-range fuel tanks, and lightweight all-alloy bodywork.

The Competition models fetch a significant premium, with the last few to reach auction being snapped up for $17,990,000 (RM-Sotheby’s | New York | December 2017), $18,150,000 (Gooding & Company | Pebble Beach | August 2016), $11,275,000 (Gooding & Company | Pebble Beach | August 2012) and $7,260,000 (Gooding & Company | Pebble Beach | August 2010). Given this car was specified with a full list of performance options, the much sought-after covered headlights, all matching numbers, a prodigious history file and the clear trend in the numbers above, and it may well surpass the $18,450,296 (€16,230,000) fetched by the ex-Alain Delon 1961 Ferrari 250 GT SWB California Spider from the fabled Baillon Collection (the world’s most expensive barn find).

1937 Mercedes-Benz 540K Special Roadster by Mayfair

Mecum

Estimate: no estimate
Mecum | Lot MG5 | 14-August-2021
Detailed Description and images
A 540K Spezial Roadster is one of the world’s greatest cars. It is a brutally fast, handcrafted, hulking art deco sculpture on wheels designed to seat two comfortably at 100 mph on Germany’s autobahn network of the thirties. The 500 K Special Roadster was one of a half dozen variants using the 5.0 liter straight eight with Kompressor (supercharger) introduced in 1934, and in 1936 it was lightened and upgraded to 5.4 liters to celebrate the fiftieth anniversary of Carl Benz’s 1886 Autowagon, which kicked off the automobile industry.

The resulting 540K engine produced 115 bhp without the supercharger engaged and 180 bhp when the compressor clutched in at full throttle giving it a top speed approaching 110 mph. When tested by Britain’s Motor magazine, the 540K hit 102 mph at the end of a quarter-mile. This performance may not seem that impressive today, but this was incredibly fast eighty years ago. Apart from the speed and beauty, it also has immense presence and you really do need to see one to comprehend how big it is, and how extravagant all that metal seems for just two people. Design head Hans Nibel somehow managed to give the Special Roadster the automotive equivalent of Da Vinci’s “divine proportione” because it looks perfectly proportioned in photographs but not nearly as impressive as it does in real life.

Only 29 500 K and 25 540 K Special Roadsters were made, they were frightfully expensive and very few have survived. This car is one of the very rare 540 K Spezial Roadsters that was “dressed” outside the Mercedes-Benz factory.

1962 Aston Martin DB4GT Zagato

RM-Sotheby’s / Rasy Ran

Estimate: $11,000,000 – $14,000,000
RM-Sotheby’s | Lot 120 | 12-August-2021
Detailed Description and images
In-period, this car was the racetrack archrival of what we now know as the world’s most expensive automobile, the Ferrari 250GTO. Just 19 DB4GT Zagatos were built with just six being left-hand-drive examples. In period, it was widely acknowledged as the fastest road car in the world, having been timed at 153.5 mph. In recent years, just a few have made it to the auction block with the most recent failing to sell after a high bid of £6,300,000 ($8,369,040) at Gooding & Company’s Passion of a Lifetime auction at Hampton Court Palace on 5 September, 2020. The car had been officially estimated to sell for between £7,000,000 and £9,000,000 ($9,300,000 to $12,000,000). Add the buyers premium to that and it would have cost the high bidder US$9,232,945 had it been accepted.

The previous DB4 GT Zagato sold for £10,081,500 (US$13,323,861) (Bonhams’ | Goodwood Festival of Speed | July 2018) and the record price paid for a DB4 GT Zagato was $14,300,000 (RM-Sotheby’s | New York | December 2015), which was the most ever paid for a British car at the time of the sale.

1970 Porsche 917 K

Nat Twiss / RM Sotheby’s

Estimate: $16,000,000 – $18,500,000
RM-Sotheby’s | Lot 328 | 14-August-2021
Detailed Description and images
Cars that win the 24 Hours of Le Mans have traditionally been worth a king’s ransom, and cars that star in movies also command a considerable premium at auction, and although this car competed and crashed in the 1970 race, it is the car that won the race in Steve McQueen’s most famous motorsport movie, Le Mans.

The car had a four year in-period career with some fine results, a subsequent two-decade historic racing career but … it has since been restored to perfection in the specification and colors in which it competed at Le Mans in 1970, and the same colors in which it “won” Steve McQueen’s celebrated eponymous racing film. Hence this car may indeed be underestimated in RM-Sotheby’s official estimation of $16,000,000 to $18,500,000.

1995 McLaren F1

Mike Maez / Gooding & Co

Estimate: $15,000,000 +
Gooding & Co | Lot 36 | 14-August-2021
Detailed Description and images
One of the finest investments you could make, the McLaren F1 is appreciating like crazy and will continue to do so for the foreseeable future. In total, 64 road cars were delivered to customers before production ended. The last one to reach auction was in 2017 at Bonham’s Quail Lodge Auction and it had 9,600 miles on the odometer, selling for $15,620,000. This car was delivered new to Japan but it ticks all the boxes and it has travelled just 390 km from new in 26 years. The $15.62 million figure is a record for an F1 road car, and it will almost certainly be broken. This could be the first $20 million McLaren F1.