2009 Porsche 911 Carrera Coupe

I think as much as I fantasize about daily driving a Porsche 911 GT3 or at least using it for all my mundane tasks that require driving, it probably isn’t the best idea ever. Outside of the ride being extremely stiff, you plain old just put a bunch of wear on the car doing something any car could do. In a sense, it’s massive overkill. However, you can still can get your 911 fix by being a reasonable person and do what most people do: just buy a Carrera 2. It is still an extremely capable and rewarding sports car, but it’s also tame enough to handle the daily driving duties. Not to mention they are nearly half the price as a GT3 in the same chassis. Today, we might have one of these perfectly daily-driver 911s without spending anywhere near $100,000.

CLICK FOR DETAILS: 2009 Porsche 911 Carrera Coupe on eBay

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1964 Mercedes-Benz 220SEb Coupe

I’ll put almost any Mercedes-Benz from the golden era of the 1960s up against other car from that time period and say it was better. There is a very distinct feeling when you open the doors to one of these cars and it usually says to you “this feels different.” Everything is heavier, thicker, and more robust. Plastic? Very little if any. This is a car made of wood, leather, and steel. You pilot them as much as you drive them. Chances are, it is going to outlast you if cared for properly. Today, we have one of those cars.

This is a 1964 Mercedes-Benz 220SEb coupe. That unofficial lowercase ‘b’ is very important as it signifies this is a fuel-injected inline-six car rather than a twin-carb of the standard 220SE. Not that the dual carbs are bad, but rather the fuel-injection system is much easier to live with and of course much smoother. This car in Chicago is finished in a wonderful shade of red with the matching hubcaps, a black leather cabin, and that all-important wood instrument cluster binnacle. Just to add some more goodness, it’s a sunroof example as well and has a four-speed manual gearbox. What isn’t to like?

CLICK FOR DETAILS: 1964 Mercedes-Benz 220SEb Coupe on eBay

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2015 Mercedes-Benz S550 Coupe

Just in under the wire, we might have one of my most favorite cars of the year. It isn’t the rarest or even the most exciting car to drive, but it is one I would be totally happy driving 365 days a year in 2022. This is a 2015 Mercedes-Benz S550 4MATIC Coupe finished in Emerald Green Metallic over a Designo brown leather interior. I like to describe it as a torpedo of luxury. This is a car that hangs in the class of Bentley Continental GT and Rolls-Royce Wraith for a fraction of the price, while looking like it totally belongs. It is hard to to believe this car is already seven years old, but that just means it isn’t $150,000 anymore. Even better, it’s got just 6,300 miles.

CLICK FOR DETAILS: 2015 Mercedes-Benz S550 Coupe on eBay

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1993 Porsche 911 Carrera 2 Coupe

Seemingly out of the no where, the 964 Porsche 911 Carrera 2 has turned into quite the valuable asset – if you want to call them that. Just this month we saw two black Carrera 2 examples sell for $124,000 and $123,456. Outliers in the grand scheme of things? Sure. However, that doesn’t mean it won’t be the start of a trend or sellers thinking their rose has finally bloomed and asking for prices in line with that. Case in point, this Japanese-spec 1992 Carrera 2 finished in the wonderful Wimbledon Green Metallic. It even has some extra fun stuff like Cup 1 wheels and the factory sport seats. The price? Well, if you were in on those black examples, you’re in the right ballpark.

CLICK FOR DETAILS: 1992 Porsche 911 Carrera 2 Coupe on eBay

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1977 Mercedes-Benz 300D ‘Coupe’

Just when I thought I’ve seen it all! What we are looking at is a 1977 Mercedes-Benz 300D that somehow was transformed into a strangely proportioned coupe. According to the seller, the body was modified by removing the rear doors, moving fuel tank and fuel door two feet forward, and extended the trunk lid two feet. Try to wrap your head around that. On top of that, this car already exists and Mercedes made of ton of them! Unless this car was modified right in 1977 when it came out, it made no sense why someone would do this. But here it is, in all its mis-proportioned glory. Just to make it even stranger, it is powered by a 1983 OM617 Turbodiesel engine. Let’s take a look:

CLICK FOR DETAILS: 1977 Mercedes-Benz 300D ‘Coupe’ on eBay

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2002 Porsche 911 Carrera Coupe

As the 996 Porsche 911 glow-up continues to gain steam, more and more of them are coming out of the woodwork at eyebrow raising prices. I still think the black sheep of the 911 family is going to stay that, but they just won’t be as cheap as they once were. Worth it? That is up to you of course, but I think a lot of these prices are reflective of people getting priced out of other 911s, simply grabbing what they can afford, and making the best of it.

Today, we have a 2002 Carrera 2 up for sale in New York with just 18,000 miles. Despite being just the base model, it was a not cheap at all. This one rang in at an impressive $96,810 when new, which was crazy to justify given the Turbo started at $110,000. Still, it is just the base 996 at the end of the day. How pricey could it be? Buckle up!

CLICK FOR DETAILS: 2002 Porsche 911 Carrera Coupe on eBay

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2001 Porsche 911 Turbo Coupe

Hard to believe we are here, or maybe not, but the best of the best 996 Porsche 911 Turbos are transacting for over $100,000. I suppose it was inevitable as rising tides lift all boats, but I didn’t see it coming this fast. Keep in mind I’m talking about the standard 996 Turbo, not the GT2 or GT3, as those are already well into their own categories of crazy growth. Still, would you take this over a classic 930 Turbo? I’m not sure.

CLICK FOR DETAILS: 2001 Porsche 911 Turbo on eBay

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1995 Mercedes-Benz E36 AMG Coupe

The Mercedes-Benz E36 AMG Coupe is not a car that comes up for sale often. Most of that has to do with there are reportedly only 68 of them in total, with 24 of them being right-hand drive cars for the UK market. So when you see them, take a closer look. What we have today is a 1995 up for sale in Germany with an impressive color combination and a price to match. At least, I think that’s the case.

CLICK FOR DETAILS: 1995 Mercedes-Benz E36 AMG Coupe at German-Car.Net

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1991 Audi Coupe Quattro

It hasn’t been all that long since I looked at a 7A-powered 90 or, for that matter, a very clean Coupe Quattro:

1990 Audi Coupe Quattro

However, today’s car – while broadly similar to that Coupe above, is definitely worth a closer look. That’s because it has a scant 27,000 miles on the clock. How is that even possible?

CLICK FOR DETAILS: 1991 Audi Coupe Quattro on eBay

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2015 Mercedes-Benz S63 AMG Coupe

In my opinion, the Mercedes-Benz S-Class AMG coupe is as close as a personal jet you can on four wheels. I’ll put it up against any current offering from Bentley and Rolls-Royce and say it is better. Decade after decade, Mercedes seems to do it right with these and the prices reflect that. Funny how that works. The C217 generation that just wrapped up production raised the bar again. The example I wanted to look at today, a 2015 S63 AMG, is now a hard to believe six-years old, but still could pass as a new car. The price? Take about $100,000 off the sticker. Sounds like a deal, right? Not just yet.

CLICK FOR DETAILS: 2015 Mercedes-Benz S63 AMG Coupe on eBay

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