2021 Chaparral Boats 21 SSI OB — Sebastian, Florida

A 2021 Chaparral 21 SSi OB at Sebastian, Florida, asking $55,500 through popsells.com. The 21 SSi OB is Chaparral's outboard runabout — the yard's step up from its entry H2O series, the same family-dayboat brief with more finish, built around a single Yamaha outboard on a transom bracket. The type's public reputation is uncomplicated: quick onto plane, mid-40s flat out with the 200-horse option, an aft sundeck that folds to a lounge rather than pretending at accommodation.

Two honesty notes. We hold no sister 21 SSi OB to benchmark against, so the model's own market is silent here. And our record carries no condition, hours or kit — the year, the length and the ask are what we can place; we have not surveyed her.

What the shelf does place is the position: $55,500 makes this the most expensive 21–22-foot bowrider we hold. The other four ask $19,900 to $49,950, and what the premium buys is age — this is the newest small bowrider on the shelf by two years. That crowded cheaper end is a page of its own: the bowriders under $50k.

The cross-check that matters is the 2019 Crownline 215 SS at Fairborn, Ohio — the same 21-foot brief, two years older, $15,550 less:

Where the opposite instinct leads — pay more, get more — the 2023 Cobalt 23SC at Branson is the upgrade on every front, two years newer and two feet longer for $23,000 over this ask:

And the yard's own budget door is the 2016 Chaparral H2O at Ashland, Virginia — the simpler line this model grew out of, $35,600 under this boat:

But if the point is the newest small bowrider on this shelf, that is this boat — the one to survey first: