2008 Regal Regal 2860 Window Express — Winthrop Harbor, IL 60096

A 2008 Regal 2860 Window Express at Winthrop Harbor, Illinois, asking $49,995 through SkipperBud's Northpoint. Regal has been family-owned at Orlando since 1969, and this size is its home ground: three J.D. Power awards for express cruisers of 24 to 33 feet. The Window Express name is the design idea: cats-eye windows flush in the cabin sides under the windshield, more across the cabin front, so the mid-cabin gets daylight instead of a porthole. Built 2006 to 2011; 29.42 ft on a 9.5 ft beam.

Two honesty notes. We hold no other 2860, so there is no sister ship to benchmark this ask against. And our file carries no condition note and no days-on-market — those are the broker's and the surveyor's questions, not ours.

What the shelf does place is the price. It clears the under-$50k line by five dollars and then stands at the top of that band alone: every other cruiser we hold under $50,000 asks $35,000 or less, and nothing among its comparables asks between $35,000 and $60,900. It is the expensive end of cabin cruisers under $50k, defensible only if the boat is as good as its year suggests — which our file cannot tell you.

The cheapest way to test it is the yard's own smaller boat — the 2008 Regal 2565 Window Express at Nanuet, New York, two feet shorter and $14,995 less:

Blunter still, the 2008 Four Winns 278 Vista at Sanford, Florida asks $29,495 less for the same vintage at 27 feet:

Going the other way, the 2018 Rinker 290 Express Cruiser at Miami is ten years newer and two feet longer for $35,005 more:

But if it is the lit cabin you are buying, nothing else on this shelf does it — this is the one to survey first: