2008 Porsche Cayman S with 19k Miles


Look, mane. I want a 2014+ Cayman just as much as you do. Too bad you can’t get one for much less than 40 grand. So what about this first generation Cayman S?

2008 cayman s


I feel like the current-gen Cayman had the effect of immediately making this generation look dated…but for the price, that’s a hell of a car. And it won’t drive dated. Extra points for the lack of nav screen.


Definitely a lot of car for the money. If you wait until the 2009 model year, you can get one without the dreaded IMS bearing. More cash, but I’d sleep better without thoughts of IMS bearing implosions dancing in my head.

Sadly, this particular example appears to have been in an accident (according to the Carfax report), so if you’re truly in the market you should probably skip this one and look for another accident-free specimen.

I would also point out that you can get a really nice 996-generation 911 for this kind of money, even one that’s already had its IMS bearing replaced. It’s perhaps not as “pure” as the Cayman, but by God it’s a 911.


I second getting a 2009 and newer “987.2” Cayman w/o the IMS.

'09+ cars also received exterior and interior updates, slightly larger engines with more power (265hp for the base and 320hp for the S), available PDK transmission, standard 6 speed manual for the base car (vs 5sp before) among other notable changes.

The price increase between a 987.2 versus 987.1 is well worth it.