• Boats
  • Chaparral
    Within 100 Miles Of
    Madison, Wisconsin

Filter Boats By

Filters

from

Boat Make / Model

Chaparral boats for sale in Madison Wisconsin

There are 35 new and used Chaparral boats for sale in Madison, Wisconsin. Browse Chaparral boat types like Bowrider, Deck Boat, and Ski & Wake on BoatCrazy. View a wide selection of Chaparral boats from $24,750 to $391,445.
Madison, Wisconsin Boats For Sale
  • Back
  • Boats
  • Chaparral
    Within 100 Miles Of
    Madison, Wisconsin
35 boats found within 100 miles from Madison, Wisconsin
Back
Filter
  • 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

    $35,000
    Waterford, WI
    • Waterford, WI
    • Bowrider
    • 28'
    • 2004 / Used
    • $35,000

    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
    $35,000
    VIEW DETAILS
  • 2027 Chaparral SSX

    2027 Chaparral SSX

    $253,401
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 26'
    • 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
  • 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 SSi

    2027 Chaparral SSi

    $74,775
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 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
  • 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

    $66,680
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2026 / New
    • $66,680

    Sharp black-hull 21 SSi with max 250 HP power, upgraded comfort and the right equipment for cruising, tubing and everyday lake days.Highlights: Mercury 4.5L 250 HP Deluxe Package... View Details

    View 30 Photos and Details Contact Seller
    $66,680
    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

    $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
  • 2027 Chaparral SSi

    2027 Chaparral SSi

    $77,350
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 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
  • 2027 Chaparral SSX

    2027 Chaparral SSX

    $184,953
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 24'
    • 2027 / New
    • $184,953

    A bold, premium bowrider combining upscale styling, strong performance and a long list of desirable upgrades. Highlights: 300 HP Mercury DTS Sterndrive with Bravo Three Drive Blac... View Details

    View 37 Photos and Details Contact Seller
    $184,953
    VIEW DETAILS
  • 2022 Chaparral SSi

    2022 Chaparral SSi

    $49,495
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 2022 / Used
    • $49,495

    Turn heads with this 2022 Chaparral 21 SSi! Powered by a Mercury 250 HP engine, this sporty bowrider combines sleek styling, premium comfort, and exciting performance for endless f... View Details

    View 38 Photos and Details Contact Seller
    $49,495
    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 SSi

    2027 Chaparral SSi

    $75,650
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 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
  • 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 SSi

    2027 Chaparral SSi

    $86,575
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 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
  • 2027 Chaparral SSi

    2027 Chaparral SSi

    $100,455
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 23'
    • 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
  • 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 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
  • 2027 Chaparral OSX

    2027 Chaparral OSX

    $391,445
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 30'
    • 2027 / New
    • $391,445

    A premium new-model bowrider loaded with standout upgrades, combining Chaparrals upscale SSX styling with strong Mercury performance and a well-appointed cockpit. Highlights: 300 H... View Details

    View 40 Photos and Details Contact Seller
    $391,445
    VIEW DETAILS
  • 2027 Chaparral SSi

    2027 Chaparral SSi

    $74,775
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 21'
    • 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
1 to 21 of 35 boats found.
Prev Next

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.