My dream car, or rather cars, will be a set of the following two cars: 1999 W140 S600 loaded with every option ($155,000 sticker when new) and a 2005 W220 S500 4MATIC also loaded up ($107,000 sticker new). I'd definitely want the W140 in any form (like an S320) for now. However for some reason all the well maintained ones I come across cost way over $15K

David, you definitely got a great deal on yours. Hopefully I'll be as lucky some day. I plan on acquiring my dream S600 by December 2005. Here's hoping.

I do agree that condition is the main factor affecting the price these old cars can fetch. But even a well maintained car that's in great shape with 400,000 miles won't be very attractive to me especially if it is still running on original engine and transmission. The reason for this being that it is obvious that with such high mileage those things would be needing $$$ spent on them pretty soon.

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1999 Mercedes-Benz S600, 103K miles - garage queen
1988 Mercedes-Benz 560SEL, 89K miles - daily driver
2007 Hyundai Sonata Limited, 31K - daily driver