2008 Four Winns Four Winns 278 Vista; V285 — Sanford, FL 32771

A 2008 Four Winns Vista 278 at Sanford, Florida, asking $20,500 — with the headline buried in the engine bay: a rebuilt Mercury with 37 hours and receipts available for review under contract. Freshwater history, shore power with AC and heat, full camper canvas, windlass, Lenco tabs, a six-blade stainless prop, and both a newer Garmin and the factory Raymarine at the helm.

The rebuilt engine is the discount and the diligence item in one. A 2008 hull at $20,500 sits well under the affordable-cruiser median of $29,900, and the rebuild is why — whoever verifies those receipts buys the youngest drivetrain-and-hull pairing on this shelf for eighties-boat money. Have a mechanic read the paperwork, then run compression anyway, and test the AC, pressurized water and windlass under load.

The honest alternatives start with its own vintage: the Regal 2565 Window Express is the same 2008 with the glass-salon layout, for a third more:

Where proven beats young, the Monterey 276 is the older deep-V with a price already cut:

And the top of the band shows what fifty thousand buys — the Regal 2860, a size up:

If the receipts read clean, this is the youngest drivetrain on the shelf — start here: