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On the market

2008 Regal 2565 Window Express — Bardonia, New York 10954

$35,000

2008 · 25.0 ft · Pop Yachts · The design file

2008 Regal 2565 Window Express

Photo: the broker's listing ↗

A 2008 Regal 2565 Window Express at Nanuet, New York, asking $35,000 through Pop Yachts. The Window Express idea is in the name: a band of hull glass lighting a mid-cabin, so 27 feet sleeps and lives like a bigger boat — daylight and berths bought at the cost of the cockpit sun pad. Regal drew it to trailer, beam kept inside the towing limit, and ran the model only a few seasons in the late 2000s.

Two honesty notes. We hold no other 2565, so there is no sister ship to price this one against — every comparison below is to a different model. And our file carries no condition note, no engine hours and no days-on-market. We have not seen this boat; nothing here is a survey.

What the shelf does place is the position. At $35,000 it is the dearest boat we hold on the cabin cruisers under $50k shelf; the 26- to 31-footers under it ask $15,000 to $20,000 and are all a decade or more older. The tighter question is a 2008 Four Winns 278 Vista in Florida — same year, same 27 feet — asking $14,500 less. What buys that gap is not in our file:

Four Winns Vista 278
Four Winns Vista 27823 on the market · 11 sites · no asks held · 1990–2005 as of 2026-08-31 — Same year, same length, $14,500 less — the price question this ask has to answer.

Regal's own answer one size up is the 2860 Window Express: the same series and the same 2008 season with two more feet of it, at Winthrop Harbor for $14,995 over this one.

Regal 2860 Window Express
Regal 2860 Window Express20 on the market · 9 sites · no asks held · 1995–2005 as of 2026-08-31 — The same idea one size up — same year, two more feet, $14,995 more.

And where the money goes into years instead of length, a 2013 Monterey 260 SCR in Oklahoma is the same 27 feet five years newer, at $71,999.

Monterey 260 SCR
Monterey 260 SCR9 on the market · 7 sites · no asks held · 2005–2010 as of 2026-08-31 — Same length, five years newer, $36,999 more — the upgrade on age.

This is a mainstream powerboat asking a price that assumes a good history, so the history is the purchase — this is the one to survey first:

View this 2008 Regal 2565 Window Express at the broker ↗

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

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