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Bennington boats for sale in Leesburg Florida

There are 42 new and used Bennington boats for sale in Leesburg, Florida. Browse Bennington boat types like Pontoon on BoatCrazy. View a wide selection of Bennington boats from $21,500 to $169,714.
Leesburg, Florida Boats For Sale
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  • Bennington
    Within 100 Miles Of
    Leesburg, Florida
42 boats found within 100 miles from Leesburg, Florida
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  • 2026 Bennington S Series 20

    2026 Bennington S Series 20

    Call for price
    Rockledge, FL
    • Rockledge, FL
    • Pontoon
    • 20'
    • 2026 / New
    • Call for price

    Yamaha F115XB - 115 HP 4 Stroke 25 in - 1 115HPPre-Rig - 911168 - Yamaha Mechanical Pre-Rig (S)908224 - Dimensional Brushed Silver Logos915032 - Echomap 52CV915007 - Analog Rocker... View Details

    View 11 Photos and Details Contact Seller
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  • 2020 Bennington 25 SSRDN

    2020 Bennington 25 SSRDN

    $49,900
    Saint Augustine, FL
    • Saint Augustine, FL
    • Pontoon
    • 25'
    • 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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  • Price Drop 2023 Bennington SX22

    2023 Bennington SX22

    $21,500
    Melbourne, FL
    • Melbourne, FL
    • Pontoon
    • 22'
    • 2023 / Used
    • $21,500

    Stock #490416 Video of this vessel available at www [dot] popsells [dot] com/view/490416 Reason for selling is "Rotating Inventory to free up space". This Bennington has now bee... View Details

    View 10 Photos and Details Contact Seller
    $21,500
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  • 2022 Bennington R25

    2022 Bennington R25

    $84,950
    Saint Petersburg, FL
    • Saint Petersburg, FL
    • Pontoon
    • 26'
    • 2022 / Used
    • $84,950

    This 2002 Bennington R25 represents the absolute pinnacle of Bennington’s lineup. This R25 perfectly marries athletic, carved-turn handling with the kind of high-end luxury standar... View Details

    View 41 Photos and Details Contact Seller
    $84,950
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  • Price Drop 2026 Bennington 24 M STERN LOUNGE

    2026 Bennington 24 M STERN LOUNGE

    $127,833
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 26'
    • 2026 / New
    • $127,833

    If your idea of a perfect weekend involves a high-energy social gathering that seamlessly transitions into a sun-drenched evening cruise, this specific Bennington 24MSL is your ult... View Details

    View 23 Photos and Details Contact Seller
    $127,833
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  • 2027 Bennington 22 S1 FISH AND CRUISE

    2027 Bennington 22 S1 FISH AND CRUISE

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22'
    • 2027 / New
    • Call for price

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    View 4 Photos and Details Contact Seller
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  • 2027 Bennington 18 S CRUISE

    2027 Bennington 18 S CRUISE

    $35,931
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 19'
    • 2027 / New
    • $35,931

    Imagine a sun-drenched Saturday afternoon where the only item on your agenda is choosing which sandbar to drop anchor near. If your idea of the perfect water day involves a close-k... View Details

    View 23 Photos and Details Contact Seller
    $35,931
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  • 2027 Bennington 22 S1 FISH AND CRUISE

    2027 Bennington 22 S1 FISH AND CRUISE

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22'
    • 2027 / New
    • Call for price

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  • 2027 Bennington 20 S1 STERN RADIUS

    2027 Bennington 20 S1 STERN RADIUS

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20'
    • 2027 / New
    • Call for price

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    View 6 Photos and Details Contact Seller
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  • Price Drop 2026 Bennington 21 S FISH AND CRUISE

    2026 Bennington 21 S FISH AND CRUISE

    $59,631
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $59,631

    For the "pro-social" angler who refuses to choose between a serious morning catch and a premium afternoon lounge, the Bennington 21SFC is your ultimate dual-threat. This... View Details

    View 19 Photos and Details Contact Seller
    $59,631
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  • 2027 Bennington 21 S SWINGBACK

    2027 Bennington 21 S SWINGBACK

    $68,900
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21'
    • 2027 / New
    • $68,900

    If your idea of a perfect Saturday involves endless sun, close friends, and effortless multi-tasking on the water, the Bennington 21 S Swingback is your ultimate sanctuary. This po... View Details

    View 23 Photos and Details Contact Seller
    $68,900
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  • 2027 Bennington 22 S SWINGBACK

    2027 Bennington 22 S SWINGBACK

    $74,119
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22'
    • 2027 / New
    • $74,119

    If your idea of a perfect weekend involves gathering a dozen of your favorite people for a sun-drenched day on the water, this pontoon is calling your name. Tailor-made for the ult... View Details

    View 23 Photos and Details Contact Seller
    $74,119
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  • 2027 Bennington 22 S1 STERN RADIUS

    2027 Bennington 22 S1 STERN RADIUS

    $69,872
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22'
    • 2027 / New
    • $69,872

    If your ideal weekend involves sun-drenched cruising, non-stop tunes, and effortless hosting, the Bennington 22 S1 Stern Radius is built for you. This pontoon is designed for the u... View Details

    View 6 Photos and Details Contact Seller
    $69,872
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  • 2027 Bennington 22 S1 STERN RADIUS

    2027 Bennington 22 S1 STERN RADIUS

    $73,344
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22'
    • 2027 / New
    • $73,344

    If your dream day on the water involves hosting a lively crew, carving up wake, and soaking in non-stop sunshine, this pontoon is tailored just for you. Built for social butterflie... View Details

    View 5 Photos and Details Contact Seller
    $73,344
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  • 2027 Bennington 20 S1 STERN RADIUS

    2027 Bennington 20 S1 STERN RADIUS

    $48,254
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20'
    • 2027 / New
    • $48,254

    If your ideal weekend involves sunny sandbars, endless playlists, and kicked-back relaxation, the Bennington 20 S Stern Radius is tailor-made for you. Built for social weekenders,... View Details

    View 7 Photos and Details Contact Seller
    $48,254
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  • 2027 Bennington 20 S1 4 PT FISHING

    2027 Bennington 20 S1 4 PT FISHING

    $49,905
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20'
    • 2027 / New
    • $49,905

    Anglers who refuse to choose between serious fishing utility and supreme weekend relaxation will find their perfect match in the Bennington 20 S1 4 Point Fishing pontoon. Powered b... View Details

    View 6 Photos and Details Contact Seller
    $49,905
    VIEW DETAILS
  • 2027 Bennington 22 M SWINGBACK

    2027 Bennington 22 M SWINGBACK

    $113,193
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 24'
    • 2027 / New
    • $113,193

    Meet the ultimate vessel for entertainers, sun-seekers, and weekend socialites who treat the water like their personal floating lounge. The Bennington 22MSB is tailor-made for thos... View Details

    View 29 Photos and Details Contact Seller
    $113,193
    VIEW DETAILS
  • 2027 Bennington 20 S1 STERN RADIUS

    2027 Bennington 20 S1 STERN RADIUS

    $56,579
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 20'
    • 2027 / New
    • $56,579

    Looking for the ultimate floating lounge that turns every weekend into a high-vibe sandbar party? The Bennington 20 S Stern Radius is custom-made for the social host who loves ente... View Details

    View 5 Photos and Details Contact Seller
    $56,579
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  • 2017 Bennington 24 SXSR

    2017 Bennington 24 SXSR

    $24,900
    Palm Bay, FL
    • Palm Bay, FL
    • Pontoon
    • 24'
    • 2017 / Used
    • $24,900

    Bennington 24 SXSR Tritoon - Your Gateway to Relaxation on Water Experience the perfect blend of comfort and performance with the Bennington 24 SXSR Tritoon. Designed for those wh... View Details

    View 0 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 2014 Bennington 2274 GL

    2014 Bennington 2274 GL

    $28,997
    Bradenton, FL
    • Bradenton, FL
    • Pontoon
    • 23'
    • 2014 / Used
    • $28,997

    2014 Bennington 2274 GLEnjoy the perfect blend of comfort, quality, and timeless style with this 2014 Bennington 2274 GL, now available at Boater’s World Bradenton. If you are sear... View Details

    View 1 Photo and Details Contact Seller
    $28,997
    VIEW DETAILS
  • 2019 Bennington 23 SPDX

    2019 Bennington 23 SPDX

    $38,977
    Bradenton, FL
    • Bradenton, FL
    • Pontoon
    • 25'
    • 2019 / Used
    • $38,977

    2019 Bennington 23 SPDXExperience the perfect blend of comfort, performance, and style with this pre-owned 2019 Bennington 23 SPDX, now available at Boater’s World Bradenton. If yo... View Details

    View 46 Photos and Details Contact Seller
    $38,977
    VIEW DETAILS
Showing 22 to 42 of 42 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.