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On the market

2008 Four Winns Vista 278 — Sanford, Florida

$20,500

2008 · 27.0 ft · MarineSource · The design file

2008 Four Winns Vista 278

Photo: the broker's listing ↗

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:

Regal 2565 Window Express
Regal 2565 Window Express42 on the market · 8 sites · no asks held · 2005–2010 as of 2026-08-31 — Same 2008 vintage, the window-express layout: Regal 2565 at $35,000 with trailer.

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

Monterey 276
Monterey 2769 on the market · 6 sites · no asks held · 1995 as of 2026-08-31 — Comparable: the proven-hull route — Monterey 276, price already cut to $20,000.

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

Regal 2860 Window Express
Regal 2860 Window Express20 on the market · 9 sites · no asks held · 1995–2005 as of 2026-08-31 — The size upgrade at the band's ceiling — Regal 2860 Window Express, $49,995.

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

View this 2008 Four Winns Vista 278 at the broker ↗

✍︎ Drafted with AI, directed and reviewed by a sailor — our editorial disclaimer.

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