Four Winns 255 Sundowner 2006 vs Four Winns H4 OB 2023 - Boat Spec Comparison

Q: Which is the larger boat — the Four Winns 255 Sundowner 2006 or the Four Winns H4 OB 2023?

The Four Winns 255 Sundowner 2006 is the longer of the two at 26,0 feet overall. The Four Winns H4 OB 2023 comes in at 23,1 feet, making it roughly 2,9 ft shorter — a meaningful difference in deck room and overall on-water presence.

Q: Which is easier to trailer — the Four Winns 255 Sundowner 2006 or the Four Winns H4 OB 2023?

For trailering, the Four Winns 255 Sundowner 2006 has the edge at 491 lbs dry weight versus 4 200 lbs for the Four Winns H4 OB 2023. Add a motor (typically 300–500 lbs for an outboard in this class), gear, and a partial fuel load and the difference grows. Lighter is friendlier on smaller tow vehicles and on fuel economy while hauling.

Q: How many passengers can the Four Winns H4 OB 2023 carry?

The Four Winns H4 OB 2023 has an official capacity rating of 7 people. Capacity data wasn't available for the other model in this comparison — verify directly with the dealer.

Q: Do these boats require an oversize trailer permit to tow on US highways?

Both the Four Winns 255 Sundowner 2006 and Four Winns H4 OB 2023 share an 8 ft. 6 in. (2.59 m) beam — meaning both sit right at the 8’6" threshold that most US states use for standard-width loads. In most states you can tow at that width without a special permit, but regulations vary. Always check the rules for your state and any states you'll be passing through before your first long haul.

Q: Which boat has the larger fuel tank — the Four Winns 255 Sundowner 2006 or the Four Winns H4 OB 2023?

The Four Winns 255 Sundowner 2006 has the bigger tank at 65 gallons, versus 52 gallons on the Four Winns H4 OB 2023. That 13-gallon difference translates to roughly 39–65 nautical miles of additional range at cruising speed, depending on motor, load, and conditions.

Q: Are the Four Winns 255 Sundowner 2006 and Four Winns H4 OB 2023 from the same manufacturer?

Yes — both the Four Winns 255 Sundowner 2006 and the Four Winns H4 OB 2023 are built by Four Winns. That means shared dealer networks, common parts availability, and consistent build quality across the line. The choice between them is essentially a question of how much boat you need, not which brand you trust.

Boat Comparison

Four Winns 255 Sundowner 2006 vs Four Winns H4 OB 2023

Four Winns

Four Winns 255 Sundowner 2006

2006

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Four Winns

Four Winns H4 OB 2023

2023

View full specs →

Detailed Evaluation & Buyer Recommendation

Four Winns 255 Sundowner 2006 vs Four Winns H4 OB 2023 — Same Brand, Different Boat

The Four Winns 255 Sundowner 2006 vs Four Winns H4 OB 2023 comparison sits squarely in the category of decisions where specs alone won't tell the whole story — intended use, storage, and long-term ownership costs all factor in.

On paper these two are close siblings in the size department — Four Winns 255 Sundowner 2006 at 26,0 ft versus Four Winns H4 OB 2023 at 23,1 ft. Weight tells a clearer story for trailering families: the Four Winns H4 OB 2023 tips the scales at 4 200 lbs — 3 709 lbs less than the Four Winns 255 Sundowner 2006 at 491 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.

Bottom line: The Four Winns 255 Sundowner 2006 at 26,0 ft is the right call if deck space, comfort, and entertaining are top of your list. The Four Winns H4 OB 2023 at 23,1 ft wins on trailering ease, likely lower purchase price, and simpler docking — a solid choice for a buyer who wants more boat for less money.

General Boat Info

MakeFour Winns

Makenot available

Model255 Sundowner

Modelnot available

Model Year2006

Model Yearnot available

Measurements / Dimensions

Beam8 ft. 6 in. (2.59 m)

Beam8.50 ft

Beam - Meters2.59

Beam - Inches102

Bridge clearance - Detail6 ft. 3 in. (1.91 m)

Bridge clearance - Detailnot available

Bridge clearance - Meters1.91

Bridge clearance - Metersnot available

Bridge clearance - Inches75

Bridge clearance - Inchesnot available

Deadrise20℃

Deadrisenot available

Draft [max] - Detail36 in. (91 cm)

Draft [max] - Detail3.50 ft

Draft [max] - Meters0.91

Draft [max] - Meters1.07

Draft [max] - Inches36

Draft [max] - Inches42

Weight - Detail4,650 - 4,910 lbs. (2,100 - 2,230 kg)

Weight - Detailnot available

Weight - kg2227.14

Weight - kgnot available

Weight - lbs.491

Weight - lbs.not available

Length - Meters8.2

Length - Metersnot available

Length - Feet26

Length - Feet23.11

Length - Inches9

Length - Inchesnot available

Length [over all with swim platform]26 ft. 9 in. (8.2 m)

Length [over all with swim platform]not available

Length overall - Detailnot available

Length overall - Detail23.11 ft

Length overall - Metersnot available

Length overall - Meters7.04

Length overall - Inchesnot available

Length overall - Inches277

Draft Minnot available

Draft Min1.80 ft

Displacementnot available

Displacement4200.00 lbs

Engine and Drivetrain

Engine/s standardVolvo Penta 5.7Gi/Duoprop 280 hp

Engine/s standardnot available

Fuel tank capacity - Detail65 gal. (246 l)

Fuel tank capacity - Detailnot available

Fuel tank capacity - Liters246.05

Fuel tank capacity - Liters196.84

Fuel tank capacity - Gal65

Fuel tank capacity - Gal52

Drive typeI/O

Drive typenot available

Operational Info

HeadPorta-potti

Headnot available

Water capacity12 gal. (45 l)

Water capacitynot available

Maximum capacity2,500 lbs. (1,134 kg)

Maximum capacitynot available

Holding tank capacity - Detail2.6 gal. (9.8 l)

Holding tank capacity - Detailnot available

Holding tank capacity - Liters11.36

Holding tank capacity - Litersnot available

Holding tank capacity - Gal2.6

Holding tank capacity - Galnot available

Trailerablenot available

TrailerableYes

Boat typenot available

Boat typePower

Trailer Info

Trailer - DetailSure-Load? custom-matched

Trailer - Detailnot available

Four Winns 255 Sundowner 2006 vs Four Winns H4 OB 2023 — Common Questions

Which is the larger boat — the Four Winns 255 Sundowner 2006 or the Four Winns H4 OB 2023?

The Four Winns 255 Sundowner 2006 is the longer of the two at 26,0 feet overall. The Four Winns H4 OB 2023 comes in at 23,1 feet, making it roughly 2,9 ft shorter — a meaningful difference in deck room and overall on-water presence.

Which is easier to trailer — the Four Winns 255 Sundowner 2006 or the Four Winns H4 OB 2023?

For trailering, the Four Winns 255 Sundowner 2006 has the edge at 491 lbs dry weight versus 4 200 lbs for the Four Winns H4 OB 2023. Add a motor (typically 300–500 lbs for an outboard in this class), gear, and a partial fuel load and the difference grows. Lighter is friendlier on smaller tow vehicles and on fuel economy while hauling.

How many passengers can the Four Winns H4 OB 2023 carry?

The Four Winns H4 OB 2023 has an official capacity rating of 7 people. Capacity data wasn't available for the other model in this comparison — verify directly with the dealer.

Do these boats require an oversize trailer permit to tow on US highways?

Both the Four Winns 255 Sundowner 2006 and Four Winns H4 OB 2023 share an 8 ft. 6 in. (2.59 m) beam — meaning both sit right at the 8’6" threshold that most US states use for standard-width loads. In most states you can tow at that width without a special permit, but regulations vary. Always check the rules for your state and any states you'll be passing through before your first long haul.

Which boat has the larger fuel tank — the Four Winns 255 Sundowner 2006 or the Four Winns H4 OB 2023?

The Four Winns 255 Sundowner 2006 has the bigger tank at 65 gallons, versus 52 gallons on the Four Winns H4 OB 2023. That 13-gallon difference translates to roughly 39–65 nautical miles of additional range at cruising speed, depending on motor, load, and conditions.

Are the Four Winns 255 Sundowner 2006 and Four Winns H4 OB 2023 from the same manufacturer?

Yes — both the Four Winns 255 Sundowner 2006 and the Four Winns H4 OB 2023 are built by Four Winns. That means shared dealer networks, common parts availability, and consistent build quality across the line. The choice between them is essentially a question of how much boat you need, not which brand you trust.

← Four Winns 255 Sundowner 2006 full specs ← Four Winns H4 OB 2023 full specs