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New Bennington Boats for Sale in Winter Garden, FL: Shop New Bennington Pontoons

Showing 12 Results
  • StatusCall for Price
    LocationOrlando, FL
    Stock #WS2064

    Checkout the 2026 Bennington 23 M Swngbk by Regal and Nautique of Orlando at Orlando, FL location... READ MORE

    View Boat
    Engine Hours0
    Engine Power250
    Beam8.6
    length23
    ColorMatte black smooth
    Fuel TypeGas
    StatusCall for Price
    LocationOrlando, FL
    Stock #WS2111

    Upgrade your boating experience with quality and comfort. The L Line boasts an array of luxury standards, including a premium finish, erg... READ MORE

    View Boat
    Engine Hours0
    Engine Power250
    Beam8.6
    length23
    Colormidnight blue/matte black
    Fuel TypeGas
  • StatusCall for Price
    LocationOrlando, FL
    Stock #22MSB

    Checkout the 2026 Bennington 22 MSB by Regal and Nautique of Orlando at Orlando, FL location... READ MORE

    View Boat
    Engine Hours0
    Engine Power200
    Beam8.6
    length22
    Colormatte black smooth no accent
    Fuel TypeGas
  • StatusCall for Price
    LocationOrlando, FL
    Stock #936736

    Checkout the 2026 Bennington 22 M Open FSB by Regal and Nautique of Orlando at Orlando, FL location... READ MORE

    View Boat
    Engine Hours0
    Engine Power200
    Beam8.6
    length22
    Colormatte black smooth
    Fuel TypeGas
    StatusCall for Price
    LocationOrlando, FL
    Stock #WS8801

    Checkout the 2026 Bennington 22 MSB by Regal and Nautique of Orlando at Orlando, FL location... READ MORE

    View Boat
    Engine Hours0
    Engine Power200
    length22
    ColorMatte black smooth no accent
    Fuel TypeGas
    StatusCall for Price
    LocationOrlando, FL
    Stock #WS7962

    Experience extraordinary with M Line. Its sleek silhouette, innovative features and customizable design redefine luxury boating. READ MORE

    View Boat
    Engine Hours0
    Engine Power250
    Beam8.6
    length24
    Colormetallic white smooth
    Fuel TypeGas
    StatusCall for Price
    LocationOrlando, FL
    Stock #WS2060

    Checkout the 2026 Bennington 24 M Open FSB by Regal and Nautique of Orlando at Orlando, FL location... READ MORE

    View Boat
    Engine Hours0
    Engine Power250
    length26' 3"
    ColorMidnight blue/Matte black smooth
    Fuel TypeGas
    StatusCall for Price
    LocationOrlando, FL
    Stock #ETWS8801

    Experience extraordinary with M Line. Its sleek silhouette, innovative features and customizable design redefine luxury boating. Standar... READ MORE

    View Boat
    Engine Hours0
    Engine Power200
    Beam8.50
    length21.33
    ColorMATTE BLACK SMOOTH/BLACKOUT
    Fuel TypeGas
    Fuel Capacity33
    StatusCall for Price
    LocationOrlando, FL
    Stock #ETWS7950

    CALL OR TEXT 407-425-2628 The 2025 S series allows you to have it your way. From the bold look of the optional blackout exterior to the t... READ MORE

    View Boat
    Engine Hours0
    Engine Power175
    Beam8.5
    length23
    ColorAzzure blue smooth/gemini black
    Fuel TypeGas
    Fuel Capacity32

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Bennington has long been the gold standard in luxury pontoon and tritoon boating, offering an unmatched combination of performance, comfort, and elegance in Winter Garden, FL. With over two decades of design excellence and industry-leading construction, Bennington boats are crafted to deliver an exceptional on-water experience. From plush seating to cutting-edge performance features, every detail reflects the brand’s commitment to quality. In Winter Garden, FL, where water adventures are part of the lifestyle, our lineup of new pontoon boats for sale and new tritoon boats for sale at Regal & Nautique of Orlando brings that Bennington excellence directly to local boaters. Whether you're looking to relax with family or entertain friends in Winter Garden, FL, Bennington offers the perfect ride.

  • The Difference Between Pontoons & Tritoons

    Before selecting your next boat in Winter Garden, FL, it’s essential to understand what sets pontoons and tritoons apart. A traditional pontoon features two aluminum tubes beneath a flat deck, offering stability and smooth cruising ideal for casual outings. A tritoon, on the other hand, includes a third tube in the center, which improves weight distribution, speed, and handling for those who want enhanced performance on Winter Garden, FL’s lakes. When browsing our inventory of new pontoon boats for sale and new tritoon boats for sale, consider how you plan to use your boat, whether it be relaxed cruising, towing water toys, or navigating rougher conditions. With Bennington, both options offer premium craftsmanship in Winter Garden, FL, but tritoons give you that little extra in performance.

  • Your Guide to Choosing the Ideal Pontoon or Tritoon Boat in Winter Garden, FL

    Choosing a new boat is more than just picking a model. Rather, it’s about finding the right fit for your lifestyle. Our team in Winter Garden, FL takes time to understand your boating habits, preferences, and budget before guiding you through our selection of new pontoon boats for sale and new tritoon boats for sale. We’ll help you evaluate seating capacity, horsepower needs, and onboard features to make sure your Bennington matches your expectations perfectly in Winter Garden, FL. Every new Bennington boat Regal & Nautique of Orlando carries is backed by impressive warranties and the support of a knowledgeable local team. Visit our dealership in Winter Garden, FL and see why so many local boating families trust us when it comes to selecting their perfect new pontoon or tritoon.

Your Journey on the Winter Garden,FL Water Begins Here


As an award-winning Regal and Nautique dealership, we’re more than just a destination for premium boats, we’re your trusted partner in Winter Garden,FL, creating lifelong memories and cherished family traditions on the water. Our mission is to deliver an unparalleled buying and ownership experience, backed by a commitment to excellence in every detail.

From the moment you walk through our doors, you’ll be welcomed by a team of friendly, passionate, and highly knowledgeable professionals dedicated to helping you find the perfect boat for your lifestyle. Whether you're a first-time buyer or a seasoned boater, we strive to provide an exceptional experience that extends far beyond the sale.

We take pride in offering:

  • A world-class boat buying experience tailored to your needs and preferences
  • Top-tier boat service and maintenance to keep you on the water with confidence
  • A wide selection of premium boating accessories to enhance every adventure
  • Genuine care and personalized support from a team that truly values your satisfaction

At the heart of everything we do is a simple promise, to serve you with integrity, expertise, and a passion for the boating lifestyle. We are here in Winter Garden,FL to ensure that every step of your boating journey is smooth, enjoyable, and unforgettable.

Let us help you create experiences that will be treasured for generations.

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*Financing offered through the Regal & Nautique of Orlando Financial Services and our lending partners. Available rates are dependent on many factors including credit score, down payment, loan term, loan amount, vessel value and vessel age. Minimum credit history and down payment requirements will dictate final approval. Rates are subject to change without notice. Financing is available with approved credit (W.A.C.).The Regal & Nautique of Orlando reserves the right to withdraw any offer of financing.

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