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  • Chaparral
    Within 100 Miles Of
    Oshkosh, Wisconsin

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Chaparral boats for sale in Oshkosh Wisconsin

There are 35 new and used Chaparral boats for sale in Oshkosh, Wisconsin. Browse Chaparral boat types like Bowrider, Cruiser, and Ski & Wake on BoatCrazy. View a wide selection of Chaparral boats from $22,995 to $391,445.
Oshkosh, Wisconsin Boats For Sale
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  • Boats
  • Chaparral
    Within 100 Miles Of
    Oshkosh, Wisconsin
35 boats found within 100 miles from Oshkosh, Wisconsin
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  • 2027 Chaparral 21 SSi

    2027 Chaparral 21 SSi

    $77,350
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $77,350

    A sharp, well-equipped bowrider finished in full Island Green gelcoat with a premium Dune interior and a white folding arch tower. Highlights: Mercury MPI Sterndrive with Alpha Dri... View Details

    View 31 Photos and Details Contact Seller
    $77,350
    VIEW DETAILS
  • 2025 Chaparral SSi

    2025 Chaparral SSi

    $64,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2025 / Used
    • $64,995

    Set up for watersports and weekend cruising, with 250 HP power, a folding tower and a well-appointed cockpit thats ready for full days on the lake.Highlights: MerCruiser 4.5L 250 H... View Details

    View 37 Photos and Details Contact Seller
    $64,995
    VIEW DETAILS
  • 2026 Chaparral SSi OB

    2026 Chaparral SSi OB

    $66,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2026 / Used
    • $66,995

    Dealer demo opportunity with outboard simplicity, a folding arch and the right upgrades for easy family boating and watersports.Highlights: Mercury Pro XS 150 MTX Folding Arch Tow... View Details

    View 33 Photos and Details Contact Seller
    $66,995
    VIEW DETAILS
  • 2015 Chaparral 19 H2O Ski & Fish

    2015 Chaparral 19 H2O Ski & Fish

    $22,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2015 / Used
    • $22,995

    A versatile runabout built for owners who want to spend one day cruising and pulling watersports and the next day fishing. The Chaparral 19 H2O Ski and Fish combines the comfortabl... View Details

    View 33 Photos and Details Contact Seller
    $22,995
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

    $64,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2026 / Used
    • $64,995

    A rare current-model pre-owned opportunity, combining 250 HP performance with a black folding arch, upgraded flooring and a fully equipped helm.Highlights: MerCruiser 4.5L 250 HP... View Details

    View 23 Photos and Details Contact Seller
    $64,995
    VIEW DETAILS
  • 2022 Chaparral SSX

    2022 Chaparral SSX

    $149,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 28'
    • 2022 / Used
    • $149,995

    Low-hour luxury bowrider with big-block V8 power, premium upgrades and plenty of room for cruising and entertaining.Highlights: 380 HP MerCruiser 8.2L DTS Only 59 Hours EFX Elect... View Details

    View 40 Photos and Details Contact Seller
    $149,995
    VIEW DETAILS
  • 2027 Chaparral SSX 6

    2027 Chaparral SSX 6

    $253,401
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $253,401

    Black Edition SSX 6 with serious presence, premium comfort, and the performance to match. Powered by a 380 HP Mercury 8.2L DTS, this boat is loaded with standout upgrades for cruis... View Details

    View 36 Photos and Details Contact Seller
    $253,401
    VIEW DETAILS
  • 2027 Chaparral 21 SSi

    2027 Chaparral 21 SSi

    $74,775
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $74,775

    The Seafoam Green and black color combination gives this SSi a look that stands apart, while a folding arch, extended swim platform and upgraded SeaDek make it equally ready for cr... View Details

    View 37 Photos and Details Contact Seller
    $74,775
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

    $72,570
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2026 / New
    • $72,570

    Sporty Alloy Gray 21 SSi with max 250 HP power, a folding arch and premium upgrades for cruising, watersports and easy weekend boating.Highlights: Mercury 4.5L 250 HP MTX Folding... View Details

    View 28 Photos and Details Contact Seller
    $72,570
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

    $74,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 2026 / Used
    • $74,995

    A roomy 23-foot bowrider with 250 HP power, wraparound seating and a well-equipped cockpit for cruising, watersports and entertaining.Highlights: Mercury 4.5L 250 HP MTX Folding A... View Details

    View 26 Photos and Details Contact Seller
    $74,995
    VIEW DETAILS
  • 2013 Chaparral SSX

    2013 Chaparral SSX

    $53,495
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 25'
    • 2013 / Used
    • $53,495

    Made for big crews and long lake days, with seating for 14, strong 300 HP performance and a layout designed for cruising, lounging and watersports.Highlights: MerCruiser 5.7L 300 H... View Details

    View 39 Photos and Details Contact Seller
    $53,495
    VIEW DETAILS
  • 2026 Chaparral SSX

    2026 Chaparral SSX

    $168,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 26'
    • 2026 / New
    • $168,995

    A luxury-level bowrider built for long days on the water, with big V8 power, upscale amenities and room to entertain.Highlights: Mercury 6.2L 350 HP EFX II Electric Folding Arch... View Details

    View 40 Photos and Details Contact Seller
    $168,995
    VIEW DETAILS
  • 2012 Chaparral 206 SSI

    2012 Chaparral 206 SSI

    $27,499
    Madison, WI
    • Madison, WI
    • Bowrider
    • 20'
    • 2012 / Used
    • $27,499

    Experience Luxury on the Water The 2012 Chaparral 206 SSI is the epitome of luxury and performance, designed for the discerning boater. Its sleek lines and elegant design not only... View Details

    View 48 Photos and Details Contact Seller
    $27,499
    VIEW DETAILS
  • Price Drop 2004 Chaparral 280 SSi

    2004 Chaparral 280 SSi

    $39,995
    Waterford, WI
    • Waterford, WI
    • Bowrider
    • 28'
    • 2004 / Used
    • $39,995

    Stock #487201 Video of this vessel available at www [dot] popsells [dot] com/view/487201 Reason for selling is "Buying a smaller boat". ANY and ALL offers will be put in front o... View Details

    View 10 Photos and Details Contact Seller
    $39,995
    VIEW DETAILS
Showing 22 to 35 of 35 boats found.
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Chaparral Boats For Sale By Model (by popularity)

Chaparral Boats For Sale

New and Used Chaparral Boats

Chaparral Boats On Boatcrazy

Chaparral has been building boats since 1965. Starting in Fort Lauderdale, they moved to Nashville, Georgia in 1976, after needing larger premises.

Since then they have become one of the most respected names in the boating industry and one of the world's leading manufacturers of quality fiberglass boats. Chaparral builds a wide variety of boats, from Ski & Wake, Deck Boats, Bowriders, and Cruisers, and each one is built with the same attention to detail and commitment to quality, using state-of-the-art technology in their design process.

Search for your next Chaparral on Boatcrazy.com

Chaparral Boats Frequently Asked Questions

Chaparral boats are in the mid to upper mid-price range but they also have an entry-level line. You can view a wide selection of Chaparral boats on Boatcrazy from $5,999 to $371,999.

Chaparral boats are built with a deep V-plane which adds weight to the boat adding stability in the water, the engines are also optimized for fuel efficiency. Their line-up includes; Ski & Wake, Deck Boats, Bowriders, and Cruisers.

Chaparral produces a number of line series; SSI, SSX, OSX, SURF and VORTEX. Some of their more popular models are; 220 SSI, 257 SSX, Surf, 310 SIGNATURE, and the 23 SSI

Chaparral builds boats for all types of water activities and recreational boating. From day cruising and overnight cruising to freshwater and saltwater fishing. All watersports including wakeboarding, water skiing, and towable family fun.