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Bennington boats for sale in Orange Park Florida

There are 29 new and used Bennington boats for sale in Orange Park, Florida. Browse Bennington boat types like Pontoon and Other / Not Classified on BoatCrazy. View a wide selection of Bennington boats from $26,500 to $175,714.
Orange Park, Florida Boats For Sale
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  • Boats
  • Bennington
    Within 100 Miles Of
    Orange Park, Florida
29 boats found within 100 miles from Orange Park, Florida
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  • 2026 Bennington 20SL

    2026 Bennington 20SL

    $59,378
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20' / 0'
    • 2026 / New
    • $59,378

    Imagine a Saturday where the hardest decision you have to make is whether to lounge on the sunpad or take another lap around the lake. The Bennington 20SL is the ultimate "yes... View Details

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    $59,378
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  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    $69,210
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $69,210

    For the angler who refuses to choose between a serious fishing trip and a lively social hour, the Bennington 21SFC is the ultimate multipurpose escape. This isn't just a pontoo... View Details

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    $69,210
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  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    $69,210
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $69,210

    For the angler who refuses to choose between a serious day of fishing and a premium lounge experience, the Bennington 21SFC is your ultimate dual-threat. This layout is a dream for... View Details

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    $69,210
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  • 2026 Bennington 22SSSE

    2026 Bennington 22SSSE

    $64,972
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $64,972

    Step aboard the Bennington 22 S Stern Fishing boat, an ideal choice for anyone who loves spending time on the water, whether it's for serious angling or just cruising with love... View Details

    View 22 Photos and Details Contact Seller
    $64,972
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  • 2026 Bennington 21SFSF

    2026 Bennington 21SFSF

    $64,461
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $64,461

    Cast a line into a world where catching the "big one" doesn't mean sacrificing an ounce of style. This Bennington 21 SF is a masterclass in versatility, blending a se... View Details

    View 21 Photos and Details Contact Seller
    $64,461
    VIEW DETAILS
  • 2026 Bennington 22SFCSF

    2026 Bennington 22SFCSF

    $64,309
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $64,309

    Meet the ultimate peacekeeper for your weekend water wars. The Bennington 22 S Fish and Cruise is designed for the family that refuses to pick a lane, effortlessly blending a serio... View Details

    View 19 Photos and Details Contact Seller
    $64,309
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  • 2026 Bennington 22SSBSE

    2026 Bennington 22SSBSE

    $62,937
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $62,937

    If you're looking for a perfect blend of comfort and performance for your days on the water, this Bennington beauty is calling your name. With a spacious deck length of 21′6′ a... View Details

    View 17 Photos and Details Contact Seller
    $62,937
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  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    $70,085
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $70,085

    For the boater who wants to dominate the morning bite and the afternoon sandbar scene, the Bennington 21SFC is a masterclass in versatility. This layout is a dream for the "fi... View Details

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    $70,085
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  • 2026 Bennington 22SSB

    2026 Bennington 22SSB

    $71,667
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $71,667

    Imagine a weekend where the only "agenda" is finding the perfect cove and staying there until the stars come out. The Bennington 22SSB is the ultimate vessel for the soci... View Details

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    $71,667
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  • 2026 Bennington 22SSB

    2026 Bennington 22SSB

    $74,452
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $74,452

    If you are looking to trade the mundane for the shoreline, this Bennington 22SSB is your ultimate ticket to a permanent vacation. This boat is a socialite’s dream, designed specifi... View Details

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    $74,452
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  • 2026 Bennington 22SSR

    2026 Bennington 22SSR

    $79,660
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $79,660

    Imagine a vessel that transforms every weekend into a floating celebration. The Bennington 22SSR is the ultimate companion for social butterflies and sun-seekers alike. With a spac... View Details

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    $79,660
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  • 2026 Bennington 22SSRSF

    2026 Bennington 22SSRSF

    $79,910
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $79,910

    Ready to trade the shore for the horizon? The Bennington 22 S Stern Radius is your ultimate ticket to effortless lake days. This isn't just a boat; it’s a floating social hub d... View Details

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    $79,910
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  • 2026 Bennington 20SSRSF

    2026 Bennington 20SSRSF

    $41,729
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20' / 0'
    • 2026 / New
    • $41,729

    If your perfect Saturday involves sun-drenched cruising with a full crew of friends, the Bennington 20 SSR is your floating entertainment pad. This boat is custom-built for the soc... View Details

    View 19 Photos and Details Contact Seller
    $41,729
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  • 2026 Bennington 20SLSE

    2026 Bennington 20SLSE

    $38,997
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20' / 0'
    • 2026 / New
    • $38,997

    Ahoy there, pleasure-seekers! Feast your eyes on this beauty, a 20 S Cruise designed for those who truly appreciate the finer things in life on the water. If your idea of a perfect... View Details

    View 18 Photos and Details Contact Seller
    $38,997
    VIEW DETAILS
  • 2026 Bennington 26LXSSBASF

    2026 Bennington 26LXSSBASF

    $165,997
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 28' / 0'
    • 2026 / New
    • $165,997

    Imagine the ultimate day on the water where the only thing more striking than the sunset is your ride. This Bennington 26 LXS is the dream vessel for the social butterfly who refus... View Details

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    $165,997
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  • 2026 Bennington 26MSLSF

    2026 Bennington 26MSLSF

    $172,802
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 25' / 0'
    • 2026 / New
    • $172,802

    Imagine a sunset cruise where the conversation flows as effortlessly as the water beneath you. The M Series Stern Lounge is the ultimate sanctuary for social butterflies and relaxa... View Details

    View 26 Photos and Details Contact Seller
    $172,802
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  • 2022 Bennington 22 LS

    2022 Bennington 22 LS

    $34,350
    Orange Park, FL
    • Orange Park, FL
    • Pontoon
    • 22' / 0'
    • 2022 / Used
    • $34,350

    Step into luxury and performance with this 2022 Bennington 22LS Pontoon, powered by a Yamaha 115HP SHO outboard. Built for both relaxation and recreation, this 22-foot pontoon offe... View Details

    View 27 Photos and Details Contact Seller
    $34,350
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  • 2020 Bennington 25 SSRDN

    2020 Bennington 25 SSRDN

    $49,900
    Saint Augustine, FL
    • Saint Augustine, FL
    • Pontoon
    • 25' / 0'
    • 2020 / Used
    • $49,900

    FOR QUESTIONS CONTACT: ROBERT 202-243-8218 or rwrosso71@gmail.com2020 Bennington 25SSRDN - Saltwater Series - TritoonIncludes an EZ Loader Trailer and various transferrable warrant... View Details

    View 15 Photos and Details Contact Seller
    $49,900
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  • 2026 Bennington 21SSB

    2026 Bennington 21SSB

    $69,072
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $69,072

    If you’re the kind of person who believes a Saturday isn't complete without a sun-soaked gathering, the Bennington 21SSB is your new best friend. This pontoon is a social butte... View Details

    View 22 Photos and Details Contact Seller
    $69,072
    VIEW DETAILS
  • 2026 Bennington 21SLSF

    2026 Bennington 21SLSF

    $61,954
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21' / 0'
    • 2026 / New
    • $61,954

    If your ideal weekend involves a seamless blend of adrenaline and pure relaxation, this 21 S Cruise is your match. Dressed to impress in Luminous Blue with sleek Matte Black accent... View Details

    View 21 Photos and Details Contact Seller
    $61,954
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  • 2026 Bennington 22SSRSE

    2026 Bennington 22SSRSE

    $59,930
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22' / 0'
    • 2026 / New
    • $59,930

    If you're seeking the ultimate on-water escape, look no further than this Bennington beauty. This vessel is perfectly designed for those who love to gather friends and family f... View Details

    View 19 Photos and Details Contact Seller
    $59,930
    VIEW DETAILS
1 to 21 of 29 boats found.
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Bennington Boats For Sale By Model (by popularity)

Bennington Boats For Sale

New and Used Bennington Boats

Bennington Boats On Boatcrazy

Bennington, a luxurious line of Pontoon and Tritoon boats, is a company that sets the design trend exceeding the industry standard.

Founded in 1997 in Indiana, the company takes pride in using only the best materials and never cutting corners. With meticulous attention to detail and quality, Bennington is a leader in innovation and design for boating. Building their boats using a fully welded aluminum construction, Bennington pontoons are able to give you a safe and stable boating experience, and their Furniture is the perfect combination of comfort and support through their ergonomic design. With plenty of space and seating Bennington Pontoons are perfect for Fishing, Cruising and Entertaining.

Find your next Bennington boat on Boatcrazy.com

Bennington Boats Frequently Asked Questions

They have a good selection of models, options, and price points, depending on what model yo choose. They also have a lifetime structural and decking warranty on all their boats. You can view a wide selection of Bennington boats on Boatcrazy from $14,995 to $179,990.

Bennington's luxury Pontoon and Tritoon boats are known for their high-quality design and performance. Their Tritoons are able to handle rough and choppy waters because of the third toon. This helps to stabilize the boat and give a smoother ride.

Their extensive model series line-up is the Q, R, L, and S, Series. Some of the more popular models include; 23LSB, 20SLG, 21LL, and 21SXL.

Bennington pontoons are good for all water activities, day cruising on lakes and waterways, but they are also a great boat for fishing and even some water sports.