• Boats
  • Used Only
    Bennington

Filter Boats By

Filters

from

Boat Make / Model

Used Bennington boats for sale

There are 185 used Bennington boats for sale. Browse Bennington boat types like Pontoon, Other / Not Classified, and Deck Boat on BoatCrazy. View a wide selection of Bennington boats from $6,995 to $189,000.
Bennington Boats For Sale
185 out of 14,841 Boats Found
Back
Filter
  • 2026 Bennington 22SSB

    2026 Bennington 22SSB

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    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

    View 20 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 26MSLSF

    2026 Bennington 26MSLSF

    Call for price
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 28' / 0'
    • 2026 / Used
    • Call for price

    Imagine the ultimate social hub that doesn't just sit on the water—it commands it. This Bennington 26 M Stern Lounge is the dream vessel for the consummate host who believes th... View Details

    View 24 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 26MSLSF

    2026 Bennington 26MSLSF

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 25' / 0'
    • 2026 / Used
    • Call for price

    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
    Call for price
    VIEW DETAILS
  • 2026 Bennington 26LXSSBASF

    2026 Bennington 26LXSSBASF

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 28' / 0'
    • 2026 / Used
    • Call for price

    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

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSRSF

    2026 Bennington 22SSRSF

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / Used
    • Call for price

    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

    View 22 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSR

    2026 Bennington 22SSR

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    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

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSR

    2026 Bennington 22SSR

    Call for price
    Fleming Island, FL

    The Bennington 22SSR is the ultimate companion for the social butterfly who believes the best days are spent surrounded by friends and family. This pontoon is masterfully designed... View Details

    View 24 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSB

    2026 Bennington 22SSB

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    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

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSBSF

    2026 Bennington 22SSBSF

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    Step aboard the Bennington 22 S Swingback and you will immediately notice that this is a craft built for the ultimate socialite. If you are the person who loves being the "hos... View Details

    View 20 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSBSE

    2026 Bennington 22SSBSE

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    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
    Call for price
    VIEW DETAILS
  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / Used
    • Call for price

    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

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / Used
    • Call for price

    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

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 21SFC

    2026 Bennington 21SFC

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / Used
    • Call for price

    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

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Bennington 21SSB

    2026 Bennington 21SSB

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / Used
    • Call for price

    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
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SSSE

    2026 Bennington 22SSSE

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    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
    Call for price
    VIEW DETAILS
  • 2026 Bennington 21SFSF

    2026 Bennington 21SFSF

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 21' / 0'
    • 2026 / Used
    • Call for price

    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
    Call for price
    VIEW DETAILS
  • 2026 Bennington 22SFCSF

    2026 Bennington 22SFCSF

    Call for price
    Fleming Island, FL
    • Fleming Island, FL
    • Pontoon
    • 22' / 0'
    • 2026 / Used
    • Call for price

    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
    Call for price
    VIEW DETAILS
Showing 169 to 185 of 185 boats found.
Prev Next

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.