Its probably a 1966 or a '67
http://www.simpletractors.com/simplicity/new_in_1966.htm
The '64 and '65 machines had black dash towers, the '68 got a different grill. That's just assuming it wasn't repainted incorrectly.
Those old Briggs can go for a while, it can probably be fixed without too much issue -- probably carb from sitting. That's given it wasn't run out of oil or doesn't have an absurd amount of hours. If you go look at it, give the engine a spin, check its got decent compression.
Engine shouldn't break the deal entirely, you can find the old cast iron briggs and kohlers for around $150 running. Easy drop in fix.
It looks like those rear tires may be shot, factor those in. Depends if you just want to get it rolling with a cheap set of turfs or replace with ags; the latter can run you a bit.
If you do replace them I'd go ags myself.
But yeah. Check for play in the bevel gear box, you want as little as possible. If something is likely to break after nearly 40 years its that. Give the rear axle tube a good look over for cracks as well, those are a pain when they go.
$250 for non-runner is a tad steep, but iirc the old Simplicities just aren't as common on the west coast -- so there's that.
I've got two '64 Landlords and I like them a lot, they're good strong little machines.