Here’s three cheap 11 year old Mercedes unicorns, all different rides although powered by the same 5.5l 382 hp powerplant, and all in their own way be a hoot to own and drive. Reliable E550 family sedan, JR Ewing SL550 drop top, and a luxobarge S550 each for the price of a Honda. And with MaxCare, no high unexpected repair bills. What’s not to like? Check them out below.
Sorry only one outside shot of the SL550 on the CarMax page so far, so the interior will have to do. But this is a hard top convertible loaded with seats that heat, cool, massage, and serve up cappuccino. Great Bose stereo (used to own a Merc with one!) and the sport package. This Car and Driver review from 2007 called the car “Very entertaining for a car so aloof in the city.” Driven about 5,000 miles yearly this car is just getting broken in, and seems like a decent ride for $22k. Find this 2008 Mercedes SL550 here in Tacoma. If the link is broken the car is sold, on hold, or being transferred. 
Also in the “drive rich” category is this gigantic and stupidly well equipped 2008 S550. Yeah, you’ll either love the look of the NASCAR black wheels, or you’ll think it looks like it’s riding on four spares, but the look is unarguably sinister. But…the car has my beloved night vision option for avoiding livestock, or hauling SEALS on raids, and has 4matic AWD – a great all weather big car with all the S-class luxury. And the seats look like they are made from very expensive baseball gloves. Car and Driver reviewed the 2007 version and noted it was quieter than a Bentley. This was probably a $90-100,000 car back in the day and at $20,998 is one of the cheapest S-class CarMax cars you’ll find, and of course, MaxCare is a must. I had an S-Class (Guenther) and expensive shit goes wrong. Find this 2008 Mercedes S550 here in Los Angeles.
If you’ve read this blog before, you may know the W211 body style – the 2002 to 2009 E class, is one of my all time favorites. It is as proportional as a well-fitting suit. My New Year’s malaise made me miss an E63 that surfaced on CarMax earlier this month, but this E550 caught my eye today. The combination of looks, dirt cheap price ($16,998….really?!) and only 37,000 miles makes this one tempting family car. Heated and cooled seats (sorry no seat massager), bluetooth, premium package – what a bargain. Motor Trend reviewed the car and pulled off a 4.8 second 0-60 mph run, a half-second faster than the fatter S550 with the same powerplant. Love this car….Find it here in Tampa.
Looks like the S550 had the priced removed… I was super interested. Love this blog! … want to buy an 08-13 S-Class with a warranty for my wife and it looks like you have already done all the research.
Brian – price seems to vanish when cars on on hold or being transferred. Happens all the time to the almost 200 cars I have saved (bookmarked?) on CarMax’s web page. I try to get a screen shot when a car first surfaces so I can track if the price changes. I’m amazed how cheap some of the S550’s are.