The Four Winns 255 Sundowner 2006 vs Four Winns V338 2008 comparison sits squarely in the category of decisions where specs alone won't tell the whole story — intended use, storage, and long-term ownership costs all factor in.

Size is the most obvious dividing line here. The Four Winns V338 2008 measures 35,0 feet overall (2008), giving it roughly 9,0 additional feet of deck space compared to the Four Winns 255 Sundowner 2006 at 26,0 feet (2006). Weight tells a clearer story for trailering families: the Four Winns V338 2008 tips the scales at 1 209 lbs — 718 lbs less than the Four Winns 255 Sundowner 2006 at 491 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.

The Four Winns V338 2008 tops out at 5 hp. Engine specs for the Four Winns 255 Sundowner 2006 aren't listed — confirm with a dealer before selecting an outboard.Fuel capacity breaks the other way: the Four Winns 255 Sundowner 2006 carries 65 gallons versus 2 gallons in the Four Winns V338 2008. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.