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  • Chaparral
    Within 100 Miles Of
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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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  • 2019 Chaparral 237 SSX

    2019 Chaparral 237 SSX

    $47,987
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 2019 / Used
    • $47,987

    Introducing the 2019 Chaparral 237 SSX Experience a new level of luxury and performance with the stunning 2019 Chaparral 237 SSX. Perfectly designed for those who crave adventure,... View Details

    View 19 Photos and Details Contact Seller
    $47,987
    VIEW DETAILS
  • 2026 Chaparral SSX

    2026 Chaparral SSX

    $169,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 26'
    • 2026 / New
    • $169,995

    Designed for effortless days on the water, with generous seating, upscale amenities and 350 HP performance for cruising with a full crew.Highlights: Mercury 6.2L 350 HP EFX II Ele... View Details

    View 40 Photos and Details Contact Seller
    $169,995
    VIEW DETAILS
  • 2027 Chaparral 23 SSi

    2027 Chaparral 23 SSi

    $90,925
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $90,925

    A sharp, well-equipped SSi built with the upgrades that make a real difference on the water. The Alloy Gray and Black exterior is paired with Mercury MerCruiser sterndrive power, a... View Details

    View 36 Photos and Details Contact Seller
    $90,925
    VIEW DETAILS
  • 2027 Chaparral 21 SSi

    2027 Chaparral 21 SSi

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

    A sharp, well-equipped sport boat that blends Chaparrals upscale fit and finish with a versatile layout built for cruising, watersports and long days on the lake. This Biscayne Blu... View Details

    View 32 Photos and Details Contact Seller
    $74,775
    VIEW DETAILS
  • 2027 Chaparral 23 SSi

    2027 Chaparral 23 SSi

    $90,770
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $90,770

    A well-optioned SSi with a clean, upscale look and the right upgrades for cruising, entertaining and watersports. Finished in Biscayne Blue with a Cayenne interior, this build adds... View Details

    View 36 Photos and Details Contact Seller
    $90,770
    VIEW DETAILS
  • 2007 Chaparral 290 Signature

    2007 Chaparral 290 Signature

    $47,995
    Oshkosh, WI
    • Oshkosh, WI
    • Cruiser
    • 0'
    • 2007 / Used
    • $47,995

    A spacious express cruiser set up for weekends aboard, with comfortable overnight accommodations and thoughtful upgrades throughout.Highlights: 440 HP Upgraded Isotherm Cockpit Re... View Details

    View 40 Photos and Details Contact Seller
    $47,995
    VIEW DETAILS
  • 2027 Chaparral 21 SSi

    2027 Chaparral 21 SSi

    $75,650
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $75,650

    A striking, feature-rich Chaparral bowrider finished in a solid black hull with Cayenne interior and loaded with some of the most desirable upgrades available. Highlights: Mercury... View Details

    View 32 Photos and Details Contact Seller
    $75,650
    VIEW DETAILS
  • 2027 Chaparral 23 SSi

    2027 Chaparral 23 SSi

    $100,455
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $100,455

    Built with a sleek, upscale look and a strong mix of comfort, convenience and performance upgrades, this Chaparral stands out with its solid black hull, Cayenne interior and black... View Details

    View 33 Photos and Details Contact Seller
    $100,455
    VIEW DETAILS
  • 2023 Chaparral SSi

    2023 Chaparral SSi

    $48,495
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2023 / Used
    • $48,495

    A sporty, well-equipped Chaparral bowrider with premium cockpit finishes, versatile seating, upgraded electronics and SeaDek throughout the main entertaining areas. Highlights: Mer... View Details

    View 32 Photos and Details Contact Seller
    $48,495
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

    $87,195
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 2026 / New
    • $87,195

    Roomy, family-friendly bowrider with plenty of seating, strong V6 power and the features you want for full days on the water.Highlights: MerCruiser 4.5L 250 HP Simrad NSX9 Touchsc... View Details

    View 35 Photos and Details Contact Seller
    $87,195
    VIEW DETAILS
  • 2027 Chaparral 23 SSi

    2027 Chaparral 23 SSi

    $86,575
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 0'
    • 2027 / New
    • $86,575

    A sharp, well-equipped bowrider with an all-black exterior, Cayenne interior and the comfort upgrades that make long days on the water even better. Highlights: Mercury MPI Sterndri... View Details

    View 36 Photos and Details Contact Seller
    $86,575
    VIEW DETAILS
  • 2020 Chaparral SSX

    2020 Chaparral SSX

    Call for price
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 2020 / Used
    • Call for price

    A premium bowrider that gives you the upscale feel of a larger boat without sacrificing the sporty, easy-to-enjoy layout that makes a Chaparral so versatile. Premium Chaparral comf... View Details

    View 1 Photo and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Chaparral SSX

    2026 Chaparral SSX

    $169,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 26'
    • 2026 / New
    • $169,995

    Made to stand out at the dock and keep a full crew comfortable, with bold Biscayne Blue styling, 350 HP power and a feature-rich cockpit.Highlights: Mercury 6.2L 350 HP EFX II Ele... View Details

    View 37 Photos and Details Contact Seller
    $169,995
    VIEW DETAILS
  • 2023 Chaparral SSi

    2023 Chaparral SSi

    $64,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 2023 / Used
    • $64,995

    A great step-up family bowrider with generous seating, strong 250 HP power and smart onboard storage for everything from cruising to tubing.Highlights: MerCruiser 4.5L 250 HP Seat... View Details

    View 36 Photos and Details Contact Seller
    $64,995
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

    $72,175
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2026 / New
    • $72,175

    Sporty, easy-to-handle bowrider with max 250 HP power and the right upgrades for cruising, watersports and long days on the lake.Highlights: Mercury 4.5L 250 HP MTX Folding Arch T... View Details

    View 27 Photos and Details Contact Seller
    $72,175
    VIEW DETAILS
  • 2020 Chaparral SSX

    2020 Chaparral SSX

    $89,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 25'
    • 2020 / Used
    • $89,995

    A head-turning SSX with strong 350 HP performance, bold black-and-lime styling and an upscale cockpit built for entertaining from bow to stern.Highlights: Mercury 6.2L 350 HP EFX... View Details

    View 30 Photos and Details Contact Seller
    $89,995
    VIEW DETAILS
  • 2021 Chaparral Surf

    2021 Chaparral Surf

    $64,995
    Oshkosh, WI

    Built for riders who want more than a standard bowrider, this 23 Surf combines wake-sports capability with plenty of comfort for cruising and sandbar days.Highlights: Volvo Penta 2... View Details

    View 37 Photos and Details Contact Seller
    $64,995
    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
  • 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
  • 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 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
1 to 21 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.