Without knowing what kind of price you are starting at, "$250 less" is kind of interesting, but irrelevant information. You can get 255/50R20 tires for as little as $4xx set +balance/tax all the way up to about $2,x.. set +balance/tax.
Only way to know for sure is to test fit/drive them. Check with your tire shop to see what their policy is.
Tire sizing is not "exact" though, so that is why you need to actually take measurements. Those online sizing calculators just extrapolate sizing and make comparisons based on the inputs entered, not the actual measurements of the tires you may/will buy. You'd really need to mount them and measure height and width as a tire in one brand is not necessarily exactly the same measured diameter/height/width as the same size tire of another brand. You may also get some variance in actual measurements as you have 8.5" rims and a 275 is more suited for a 9.5-10" wide rim.
Come to think of it, I think the biggest diameter you can go without contacting suspension components on stock ride height is ~31" diameter. You may need a lift to clear ~32" diameter tires. Go do some reading in the lifted 5g threads to see what sizes they are getting away with and what mods you may need to make to run them.