1981 Bennington boats for sale in Webster, Massachusetts

2025 Bennington S Quad Bench 20 SSR

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Webster, Massachusetts

This tri-toon is loaded with options such as the Blackout Package and is ready for all your water sport activities with the 115hp Yamaha!

Trim 20 SSR

2025 Bennington LX Sport Swingback 23 LXSSB

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Webster, Massachusetts

Ride in style with the sleek and sporty LX Sport Line. With a striking silhouette, unmatched performance, and a suite of standard luxe amenities, the LX Sport stands out on the water.

Trim 23 LXSSB

2025 Bennington L L-Bench 20 LLG

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Webster, Massachusetts

We love the new matte Luminous Blue, how about you? Come see it first hand soon!

Trim 20 LLG

2025 Bennington SX L-Bench 20 SXLG

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Webster, Massachusetts

Adding an electric engine to this Bennington 20 SXLG is an interesting and eco-friendly option, providing quiet, emissions-free operation, especially for lakes and ponds with gasoline restrictions!

Trim 20 SXLG

2025 Bennington SX L-Bench 20 SXLG

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Webster, Massachusetts

We are VERY excited for this new color of Purple! Come see it yourself, we are confident you will love it as well!

Trim 20 SXLG

2021 Bennington 23 LTFB

$79,500

Webster, Massachusetts

Experience Bennington's signature series, the "Bowrider" with the industry's only step down bow! This boat comes with a brand new 250hp, and a bunk trailer!

Trim Base

2025 Bennington 18 SLX

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Webster, Massachusetts

Introducing to the color lineup for 2025 Bennington, is the new Olaedo Gold, paired with the smooth silver panel on this sharp looking 18 foot Bennington!

2025 Bennington 18 SLX

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Webster, Massachusetts

Introducing to the color lineup for 2025, is this new Absolute Red, featured on this absolutely loaded 18 foot Bennington!

2024 Bennington 20 SXSNP

$43,995

Webster, Massachusetts

S-SERIES FISHING MODEL THAT REALLY POPS ON THE WATER WITH THE NEW LUMINOUS BLUE, EQUIPPED WITH LIVE WELLS, SWIVEL CHAIRS AND A GARMIN FISH FINDER. READY FOR THE BIG CATCH!

Trim Base

2024 Bennington 22 LSB

$64,995

Webster, Massachusetts

NEW UPGRADES ON THE L-MODELS LIKE WINGED BENNINGTON LOGOS ON THE EXTERIOR AND INTERIOR REALLY HELPS THESE MID-LEVEL BOATS STAND APART!

Trim Base

2024 Bennington 23 RXSBA

$175,995

Webster, Massachusetts

Let us introduce you to the RX Sport! New to Bennington for 2024 is the Phantom Black interior! This boat also features the ALL NEW Yamaha 350hp V-6 engine! This is TRULY a MUST SEE boat!

Trim Base

2023 Bennington 23 LSB

$58,995

Webster, Massachusetts

The listed price on this 23 foot L series swingback includes the Yamaha V-max 115. The satin black is stunning on this beautiful Bennington!

Trim Base

2013 Bennington 2250 GSR

$29,995

Webster, Massachusetts

Powered by a 2021 Yamaha VF115 - Enjoy the best of boating well into the fall with this Bennington featuring a full enclosure! This boat comes with individual seat covers, raised helm, portable cupholders, and more! In the water and ready for quick delivery!

2021 Bennington 20 SLX

$34,995

Webster, Massachusetts

Showroom condition! Powered by a brand-new Yamaha VF90 - Depth finder, cover, portable cupholders, stainless docking lights, LED Lighted bimini. In-water & ready for quick delivery! See it today!

Trim Base

2011 Bennington 2275 GSi

$19,995

Webster, Massachusetts

2011 Bennington 2275 GSi Quality Family Cruising The Bennington G Series meets your desire for class, quality and comfort without sacrificing eye-appeal or amenities. Varieties of floorplans include the ability to cruise, fish, ski and simply relax on the water. Models 20 feet and above offer an innovative Extended Aft Deck option that makes boarding, ski prep and maintenance even easier than you thought possible. In addition, a comfortable automotive-style helm station keeps the captain happy. Add ESP Performance or the new Express Performance Package to most models for sport performance. - Comes with Yamaha 60hp motor, stereo, bimini top, cover, and more