Skip to main content

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

Showing 58 Results
    StatusCall for Price
    LocationOrlando, FL
    Stock #57023+

    2025 SUPER AIR NAUTIQUE S21 CALL OR TEXT 407-425-2628 The Super Air Nautique S21 brings class-leading performance and modern aesthetics ... READ MORE

    View Boat
    Engine Horsepower400
    Length21.5
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.33
    Draft32
    Dry Weight0
    Passengers14
    Interior ColorHAZE GREY/TUNGSTEN/CAPTIVA GREEN
    Exterior ColorHAZE GREY/TUNGSTEN/CAPTIVA GREEN
    Fuel TypeGas
    Fuel Capacity47
    StatusCall for Price
    LocationOrlando, FL
    Stock #54053

    2025 Super Air Nautique Nautique G23 CALL OR TEXT 407-425-2628 Celebrating its tenth year as the world’s leading wake sports boat, the S... READ MORE

    View Boat
    Engine Horsepower450
    Length23
    Hull ConstructionFIBERGLASS
    Engine Hours1
    Beam8.5
    Draft31
    Dry Weight6000
    Passengers16
    Interior ColorSAHARA SAND/JET BLACK
    Exterior ColorSAHARA SAN/JET BLACK/CENTENNIAL BLK MF
    Fuel TypeGas
    Fuel Capacity65
    StatusCall for Price
    LocationOrlando, FL
    Stock #51019

    2025 SUPER AIR NAUTIQUE G21 CALL OR TEXT 407-425-2628 COASTAL Get ready to embrace the legendary wakes and waves of the Super Air Nautiq... READ MORE

    View Boat
    Engine Horsepower450
    Length21
    Hull ConstructionFIBERGLASS
    Engine Hours1
    Beam8.6
    Draft31.25
    Dry Weight5800
    Interior ColorHAZE GREY/MYSTIC WHITE/ANTHRACITE
    Exterior ColorMYSTIC WHITE/ANTHRACITE MF/JET BLACK
    Fuel TypeGas
    Fuel Capacity47
    StatusCall for Price
    LocationOrlando, FL
    Stock #58145

    2025 SUPER AIR NAUTIQUE GS22 CALL OR TEXT 407-425-2628 Striking the perfect balance of multi-sport performance, the Super Air Nautique G... READ MORE

    View Boat
    Engine Horsepower400
    Length22
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.3
    Draft32
    Dry Weight4900
    Passengers15
    Interior ColorHAZE GREY/TUNGSTEN
    Exterior ColorMYSTIC WHITE/TUNGSTEN GREY
    Fuel TypeGas
    Fuel Capacity59
    StatusCall for Price
    LocationOrlando, FL
    Stock #46009

    2024 COASTAL SUPER AIR NAUTIQUE S25 CALL OR TEXT 407-425-2628 2024 COASTAL EDITION Designed to accommodate larger crews, the Super Air N... READ MORE

    View Boat
    Engine Horsepower450
    Length25
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.3
    Draft32
    Dry Weight5800
    Passengers18
    Interior ColorMYSTIC WHITE/MASTERS BLUE/JET BLACK
    Exterior ColorMYSTIC WHITE/MASTERS BLUE MF
    Fuel TypeGas
    Fuel Capacity86
    StatusAvailable
    LocationOrlando, FL
    Stock #50036

    2025 SUPER AIR NAUTIQUE GS20 CALL OR TEXT 407-425-2628 Striking the perfect balance of multi-sport performance, the Super Air Nautique G... READ MORE

    View Boat
    Engine Horsepower400
    Length20
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.3
    Draft32
    Dry Weight4900
    Passengers12
    Interior ColorMYSTIC WHITEANTHRACITE/JET BLACK
    Exterior ColorMYSTIC WHITEANTHRACITE MF
    Fuel TypeGas
    StatusCall for Price
    LocationOrlando, FL
    Stock #54016

    2025 Super Air Nautique Nautique G23 CALL OR TEXT 407-425-2628 Celebrating its tenth year as the world’s leading wake sports boat, the S... READ MORE

    View Boat
    Engine Horsepower450
    Length23
    Hull ConstructionFIBERGLASS
    Engine Hours14
    Beam8.5
    Draft31
    Dry Weight6000
    Passengers16
    Interior ColorMYSTIC WHITE/MOJAVE BROWN
    Exterior ColorMYSTIC WHITE/MASTERS BLUE MF
    Fuel TypeGas
    Fuel Capacity65
    StatusAvailable
    LocationOrlando, FL
    Stock #53006

    2025 Super Air Nautique S23 CALL OR TEXT 407-425-2628 Delivering unrelenting performance unlike anything in its class, the Super Air Nau... READ MORE

    View Boat
    Engine Horsepower355
    Length23
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.33
    Draft31.25
    Dry Weight5500
    Interior ColorMOJAVA BROWN/MYSTIC WHITE/ADMIRAL BLUE
    Exterior ColorMYSTIC WHITE/ADMIRAL BLUE MF
    Fuel TypeGas
    Fuel Capacity65
    StatusCall for Price
    LocationOrlando, FL
    Stock #51029

    2025 SUPER AIR NAUTIQUE G21 CALL OR TEXT 407-425-2628 COASTAL Get ready to embrace the legendary wakes and waves of the Super Air Nautiq... READ MORE

    View Boat
    Engine Horsepower450
    Length21
    Hull ConstructionFIBERGLASS
    Beam8.6
    Draft31.25
    Dry Weight5800
    Interior ColorLUNAR WHITE/MYSTIC WHITE/JET BLACK
    Exterior ColorMYSTIC WHITE/LUNAR WHITE/CENTENNIAL BLACK
    Fuel TypeGas
    Fuel Capacity47
    StatusCall for Price
    LocationOrlando, FL
    Stock #58083

    2025 SUPER AIR NAUTIQUE GS22 CALL OR TEXT 407-425-2628 Striking the perfect balance of multi-sport performance, the Super Air Nautique G... READ MORE

    View Boat
    Engine Horsepower400
    Length22
    Hull ConstructionFIBERGLASS
    Beam8.3
    Draft32
    Dry Weight4900
    Passengers15
    Interior ColorSAHARA SAND/JET BLACK/MYSTIC WHITE
    Exterior ColorMYSTIC WHITE/SAHARA SAND/CENTENNIAL BLACK MF
    Fuel TypeGas
    Fuel Capacity59
    StatusCall for Price
    LocationOrlando, FL
    Stock #ETWR6134

    2025 Bennington 23L CALL OR TEXT 407-425-2628 Going well beyond premium both inside and out, the L Line offers many of our most popular ... READ MORE

    View Boat
    Engine Horsepower200
    Length23
    Engine Hours0
    Beam8.5
    Interior ColorDIAMOND PRESSED SILVER SIMTEX
    Exterior ColorZEBRA SLATE BLK SM/ACCENT METALLIC SILVER
    Fuel TypeGas
    Fuel Capacity21
    StatusCall for Price
    LocationOrlando, FL
    Stock #52054

    2025 Nautique 200 CALL OR TEXT 407-425-2628 The Ski Nautique 200 is a traditional bow waterski boat that speaks to the Nautique purist i... READ MORE

    View Boat
    Engine Horsepower400
    Length20
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam7.92
    Draft22
    Dry Weight3400
    Passengers9
    Interior ColorMYSTIC WHITE/MASTERS BLUE/JET BLACK
    Exterior ColorMYSTIC WHITE/MASTERS BLUE MF/JET BLACK
    Fuel TypeGas
    Fuel Capacity27
    StatusCall for Price
    LocationOrlando, FL
    Stock #5C005

    2025 Ski Nautique The lightest waterski boat on the market, the Ski Nautique commands the attention of every waterskier on the planet. W... READ MORE

    View Boat
    Engine Horsepower450
    Length20
    Hull ConstructionFIBERGLASS/CARBON
    Engine Hours1
    Beam7.92
    Draft21
    Dry Weight2945
    Passengers0
    Interior ColorMYSTIC WHITE/TUNGSTEN GREY/JET BLACK
    Exterior ColorMYSTIC WHITE/TUNGSTEN GREY/CENTENNIAL BLACK MF
    Fuel TypeGas
    Fuel Capacity29
    StatusCall for Price
    LocationOrlando, FL
    Stock #5P083

    2025 PARAGON P23 CALL OR TEXT 407-425-2628 FOR MORE INFO READ MORE

    View Boat
    Engine Horsepower630
    Length0
    Hull Construction0
    Engine Hours0
    Beam0
    Draft0
    Dry Weight0
    Passengers0
    Interior ColorMYSTIC WHITE/LUXTOUCH TUNGSTEN GREY
    Exterior ColorWHITE/MASTER BLUE METAL FLAKE
    Fuel Capacity0
    StatusCall for Price
    LocationOrlando, FL
    Stock #ETWS4421

    2025 23 RX SWING BACK ARCH CALL OR TEXT 407-425-2628 READ MORE

    View Boat
    Engine Horsepower300
    Length23.33
    Hull ConstructionAlum
    Engine Hours0
    Beam8.5
    Draft0
    Dry Weight0
    Passengers0
    Interior Colorgraphite
    Exterior ColorAZURE BLUE/ANTHRACITE
    Fuel Capacity0
    StatusCall for Price
    LocationOrlando, FL
    Stock #FINX0387

    2025 SUPREME S240 CALL OR TEXT 407-425-2628 2025 SUPREME S240. The introduction of the new S-Series is reshaping the Supreme Boats brand... READ MORE

    View Boat
    Engine Horsepower409
    Length24
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.5
    Draft36
    Dry Weight0
    Passengers0
    Interior ColorWHISPER GREY/FROST WHITE
    Exterior ColorWHITE FROST/STONE GRAY
    Fuel Type81
    StatusCall for Price
    LocationOrlando, FL
    Stock #FINW0397

    2025 SUPREME S220 CALL OR TEXT 407-425-2628 The 22-foot S220 is one of our new S-Series reshaping the Supreme Boats brand farther ahead ... READ MORE

    View Boat
    Engine Horsepower409
    Length22
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.5
    Draft36
    Dry Weight0
    Passengers0
    Interior ColorWHITE FROST/ELECTRIC BLUE
    Exterior ColorELECTRIC BLUE/STONE GRAY
    Fuel TypeGas
    Fuel Capacity81
    StatusCall for Price
    LocationOrlando, FL
    Stock #FINM0395

    2025 CENTURION Ri230 2025 Centurion Ri230 CALL OR TEXT 407-425-2628. Centurion’s Ri230 is twice as impressive as other boats due to its ... READ MORE

    View Boat
    Engine Horsepower400
    Length23
    Hull ConstructionFIBERGLASS
    Engine Hours26
    Beam8.6
    Draft36
    Dry Weight0
    Passengers14
    Interior ColorWHISPER GRAY/ONYX BLACK/ELECTRIC BLUE
    Exterior ColorONYX BLACK/ELECTRIC BLUE
    Fuel TypeGas
    Fuel Capacity81
    StatusCall for Price
    LocationOrlando, FL
    Stock #RGMHK919

    2024 REGAL 28 EXPRESS CALL OR TEXT 407-425-2628 Rich in amenities, features and polished good looks, the 28 Express is fully-equipped fo... READ MORE

    View Boat
    Engine Horsepower380
    Length28
    Hull ConstructionFIBERGLASS
    Engine Hours0
    Beam8.6
    Draft22
    Dry Weight7700
    Passengers0
    Interior ColorTITANIUM
    Exterior ColorGRAPHITE
    Fuel TypeGas
    Fuel Capacity73
    StatusCall for Price
    LocationOrlando, FL
    Stock #RGMHP282

    2024 REGAL 26 XO CALL OR TEXT 407-425-2628 Built for ultimate versatility with details crafted to elevate your boating experience, the 2... READ MORE

    View Boat
    Engine Horsepower300
    Length27.08
    Hull ConstructionFIBERGLASS
    Engine Hours1
    Beam8.5
    Draft19
    Dry Weight6700
    Passengers0
    Interior ColorHITCH
    Exterior Color TAHITI BEACH WHITE/BLACK/TAHITI BEACH WHITE
    Fuel TypeGas
    Fuel Capacity72

Filters

Boat Condition

Price

$
to
$

Year

to

Bennington has long been the gold standard in luxury pontoon and tritoon boating, offering an unmatched combination of performance, comfort, and elegance in Winter Park, 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 Park, 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 Park, FL, Bennington offers the perfect ride.

  • The Difference Between Pontoons & Tritoons

    Before selecting your next boat in Winter Park, 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 Park, 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 Park, FL, but tritoons give you that little extra in performance.

  • Your Guide to Choosing the Ideal Pontoon or Tritoon Boat in Winter Park, 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 Park, 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 Park, 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 Park, 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 Park,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 Park,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 Park,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.

Check Availability

* Denotes Required Field


Inquiry Type
Name(Required)
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form

Request Price

* Denotes Required Field


Name(Required)
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form
This field is hidden when viewing the form

Get Financing

Apply For Financing

*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.

2025 © Regal & Nautique of Orlando

WEBSITE & SEO by NATIVERANK

Shop Boats (407) 644-8972