I have a completely custom Winchester 70 bolt action rifle made for Palma competition. Palma competition is for .308 caliber long range iron sight shooting, so extreme accuracy is mandatory. It has a heavy match stainless steel barrel, floating action, snakewood stock with adjustable cheekplate, custom adjustable shoulderplate, and muzzle break. A very heavy, and extremely accurate gun.
I found it at Cabelas in West Virginia for $5000 without shoulderplate.... on clearance for $999. I immediately put it on layaway, took 4 months to pay it off, and it has been totally worth it since.
For most expensive, I'm currently restoring a 1972 Chevelle, which (when I'm done replacing the engine and interior, and sprucing up the paint) I should be able to sell for about $20,000 since I'm doing everything right.