The Jaguar XK-150 would be sorta achievable here in Australia (probably $100,000 and up)
If I was totally day-dreaming, why not a 300SL Gullwing Mercedes! (I'm guessing $300K and up)
Actually, I would be very tempted by an 80s era SL ($20-40K), but don't have the garage space, and registration and insurance on a "hobby" car here in Australia is well over $1,000 per year, so no...