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Chaparral boats for sale in Wisconsin

103 Boats Available

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Chaparral 310 OSX

2026

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With a fresh design focused on storage and ergonomics, the 310 OSX from Chaparral is the perfect sport boating platform. The feature-laden helm makes the captain's life easy, and the well-appointed cabin and enclosed head make long days comfortable. The standard wetbar has a refrigerator and stainless-steel sink so you can take all your favorite foods and drinks out on the water. Storage is abundant and the Vista-View lounge seat will make you want to lie in the sunshine for hours. With a multitude of luxurious standard features and an array of options to match any preference, the 310 OSX is ready for whatever the boating season brings.

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20

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Chaparral 28 Surf

2026

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With a LOA of 28 feet, Malibu Surf Gates™, and an Infinity Power Step swim platform, don't just pretend to wake surf, surf like you mean it with the 28 Surf from Chaparral. The 28 Surf is available with our most popular package ever - the Black Edition. The Black Edition package elevates the entire boating experience and all starts with premium Black Gelcoated Hullsides and Hullbottom paired with black metal finishes around the windshield. Moving to the interior, the new soft Silicone Cayenne interior with black accents will be sure to be envied by others.

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23

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Chaparral 247 SSX

2026

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The incredible 247 SSX packs more elegance, performance and innovation than family boaters have ever experienced at this widely popular length. There's no mistaking that the style lines, attention to detail and efficient use of space is SSX at its very best. Compared to other luxury bowriders in this popular size range, the 247 has a clear cut edge when it comes to seating capacity, legroom, storage space and performance.

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15

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Chaparral 30 Surf

2026

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With 30 feet of length, Malibu Surf Gates™, and enough seating capacity for the entire crew, don't just pretend to wake surf, surf like you mean it with the 30 Surf from Chaparral. The 30 Surf was designed with the most advanced technology afloat today. Dual touch screen "Glass Dash" helm is NMEA compatible and offers navigation, engine management, full gauge compliment, and can be customized to your personal preferences. Additionally, to make surfing effortless, the 30 Surf features a Simrad touchscreen interface to control all surf related functions like ballast and the Malibu Surf Gates (TM).

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18

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Chaparral 19 SSi OB

2026

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Outboard power joins quality and style in this 19 SSi. Quick to plane, full of power, and full of all the standard features that set Chaparral apart from the rest. Storage is abundant...under the seats, in the helm, in a wakeboard sized floor locker and there's also a 30 qt cooler under the back seat. From there, you will notice the full size sun lounge for those sunny days.

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15

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Chaparral GTS 6

2026

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The GTS series represents the next generation of the Surf series, offering enhanced multi-sport capabilities along with the performance that Chaparral is known for. Equipped with the GT Surf system, these boats feature customizable wake and wave generation technologies, which include Malibu Surf Gates and a touchscreen display to manage your rider's settings. Designed with safety in mind for swimmers and watersports enthusiasts, the GTS 6 is powered by a forward-facing drive and boasts a spacious cockpit with plenty of storage.

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8

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Chaparral 250 OSX

2026

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The 250 OSX packs all of your favorite Chaparral features into an affordable package with a length overall of 24' 6". Comfort, safety, and convenience are built into the DNA of each 250 OSX featuring pull-up cleats, dual fuel fills, and our diamond pattern non-skid found on almost every surface of the boat. The dual aft Vista-view lounges are the largest in class and can accommodate guests in a variety of positions with large storage tubs built beneath them for storing gear. Our luxury, appointed Envision Sio wrapped upholstery, optional bow filler cushion, and snap-in SeaDek flooring can be added for more versatility and all provide maximum comfort.

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17

Manufacturer Specification
Chaparral 21 SSi

2026

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The 21 SSi's style is captivating, but its appeal is more than skin deep. Stainless steel hardware, composite seat bases, a cockpit drainage system, an Extended V-Plane running surface, and a molded fiberglass dash are keeping with the Chaparral DNA. Step up to the 21 SSI and enjoy wraparound seat backs in the bow, an anchor locker forward, and room for everyone.

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12

Manufacturer Specification
Chaparral SSX 6

2026

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Look no further-the SSX 6 is breaking barriers and setting the standard for on-water comfort and performance. Equipped with a state-of-the-art oversized touchscreen display, the helm is designed for easy access, enhancing ergonomic navigation. The cockpit features spacious U-shaped aft seating, leading to the standard Infinity Power Step swim platform, which offers an exceptional reboarding experience. The SSX 6 is crafted with no compromises when it comes to luxury or power.

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12

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Chaparral 21 SSi Ski & Fish

2026

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The 21 Ski & Fish SSi combines the best of everything. Larger casting platforms, abundant storage, and flexible seating cockpit design. Options you won't want to be without include snap-in carpet, a bow walk-thru door, fish finder, upgraded dash and a swim platform logo mat. Additionally, you can upgrade either one or both of the standard bucket seats to an ultra-comfort pedestal complete with a flip-up front bolster. Anglers will love the protected rod storage, standard trolling motor and 70-quart livewell.

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16

Manufacturer Specification
Chaparral 21 SSi OB

2026

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When outboard power meets our 21 SSi, exellence awaits. Key options include snap-in cockpit carpet, a swim platform mat and a Velocity Folding Arch Tower. Abundant storage, ultra comfort seats, all paired with a premium stereo system truly redefines the standard in luxury on the water.

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13

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Chaparral SSX 4

2026

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The SSX 4 packs more elegance, performance, and innovation than boaters have ever experienced at this widely popular length. Its stylish lines, meticulous attention to detail, and efficient use of space-including a furnished head-showcase the SSX model line at its finest. Compared to other luxury bowriders in this popular size range, the SSX 4 has a clear-cut edge when it comes to comfort, space, and performance.

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2

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Chaparral 23 SSi

2026

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Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 23 SSi. With a ChaparralONE price including the trailer, the 23 SSi's style is captivating, but its appeal is more than skin deep. Stainless steel hardware, composite seat bases, a cockpit drainage system, Extended V-Plane running surface and a vinyl wrapped dash are keeping with the Chaparral DNA. MerCruiser and Volvo power options delivers crisp low-end, controlled midrange and exciting full throttle performance. Step up to the 23 SSi and enjoy U-Shaped cockpit seating, a spacious bow, and dual direction chaise lounge.

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12

Manufacturer Specification
Chaparral 21 SSi Ski & Fish OB

2026

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Valued for its versatility and innovation, the 21 SSi Outboard Ski & Fish is both a first rate fishing machine and a power packed family runabout. Removable fishing seats, an aft hinged sundeck and loads of storage space create a comfort level that is unprecedented. A Limited Lifetime Hull Warranty inspires confidence. Expert workmanship, time-tested construction and detail-minded rigging deliver years of trouble free fun. Paired with a helm design featuring a custom hand-stitched brow, our Yamaha gauge package provides real time data output at your fingertips. Aluminum faced gauges are accented with stainless steel bezels. Fog resistant and built to last, our high quality instruments are easily legible in all kind of lighting conditions.

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11

Manufacturer Specification
Chaparral 280 OSX

2026

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The 280 OSX is packed with premium features that make the boat feel larger than life. A double-wide bowrider seat, hardtop with skylight, and day cabin with an electric toilet are amenities that you won't want to live without after you try them. Supple silicone upholstery, thick bolster cushions, and abundant storage options make your trips comfortable and clutter-free. The Yamaha Helm master System will help you navigate tight marinas while the Bluetooth sound system blasts your favorite tunes. The double helm seat with folding armrests and flip-up bolsters let the captain and a crew member ride in style and comfort.

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16

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Chaparral SSX 8

2026

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What sets the SSX 8 apart from the competition is the perfect balance of design and performance that Chaparral has achieved with this boat. With a responsive throttle and extended V-Plane hull, the SSX 8 glides effortlessly across the water while relaxing on premium silicone upholstery. With a furnished head, built-in coolers, and the patented Infinity Power Step, a day of boating becomes hassle-free.

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11

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Chaparral 270 OSX

2026

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Chaparral is re-writing the rules on outboard boating. The 270 OSX is a trendsetter in design, performance, and function. The helm features a glass dash with dual touch screen Simrad displays. The cockpit is open, and spacious and features a multi-position sun lounger aft. The open-concept design carries forward into the bow area which features hinged storage beneath luxuriously appointed upholstery. Chaparral went to great lengths to create a powerful and agile craft that will provide a smooth ride in any kind of water. The 270 OSX was designed with the most advanced technology afloat today. Our Standard Dual 7" inch Simrad touchscreen displays with controls are NMEA compatible and offer navigation, engine management, full gauge compliment, and can be customized to your personal preferences.

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15

Manufacturer Specification

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Chaparral 310 OSX

Chaparral 28 Surf

Chaparral 247 SSX

Chaparral 30 Surf

Chaparral 19 SSi OB

Chaparral GTS 6

Chaparral 250 OSX

Chaparral 21 SSi

Chaparral SSX 6

Chaparral 21 SSi Ski & Fish

Chaparral 21 SSi OB

Chaparral SSX 4

Chaparral 23 SSi

Chaparral 21 SSi Ski & Fish OB

Chaparral 280 OSX

Chaparral SSX 8

Chaparral 270 OSX

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