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  • Chaparral
    Within 100 Miles Of
    Waterford, Wisconsin

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Chaparral boats for sale in Waterford Wisconsin

There are 24 new and used Chaparral boats for sale in Waterford, Wisconsin. Browse Chaparral boat types like Bowrider, Cruiser, Cuddy Cabin, Deck Boat, and Ski & Wake on BoatCrazy. View a wide selection of Chaparral boats from $24,750 to $225,815.
Waterford, Wisconsin Boats For Sale
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  • Boats
  • Chaparral
    Within 100 Miles Of
    Waterford, Wisconsin
24 boats found within 100 miles from Waterford, Wisconsin
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  • 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
  • 2023 Chaparral 267 SS

    2023 Chaparral 267 SS

    $135,761
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 26'
    • 2023 / Used
    • $135,761

    2023 Chaparral 267 SS Discover the thrill of luxury on the water with the stunning 2023 Chaparral 267 SS. This remarkable vessel combines cutting-edge performance with unparalleled... View Details

    View 30 Photos and Details Contact Seller
    $135,761
    VIEW DETAILS
  • 2005 Chaparral 252 SUNSESTA

    2005 Chaparral 252 SUNSESTA

    $24,750
    Antioch, IL
    • Antioch, IL
    • Deck Boat
    • 25'
    • 2005 / Used
    • $24,750

    2005 Chaparral 252 Sunesta Deck Boat, Mercruiser 350MAG MPI Bravo 3, 478 hours, 2006 Prestige Tandem Axle Trailer w/brakes, spare & swing tongue, cover, bimini, fully enclosed... View Details

    View 28 Photos and Details Contact Seller
    $24,750
    VIEW DETAILS
  • 2017 Chaparral 257 SSX

    2017 Chaparral 257 SSX

    $75,000
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 25'
    • 2017 / Used
    • $75,000

    2017 Chaparral 257 SSX 25' Bow Rider Mercruiser 6.2L, 350hp 380 hours 2017 EZ Loader Tandem Axle Trailer Garmin 741XS Stereo Power Engine Hatch Power Rear Loungers Dual Batteries w... View Details

    View 28 Photos and Details Contact Seller
    $75,000
    VIEW DETAILS
  • 2005 Chaparral 260 SIGNATURE

    2005 Chaparral 260 SIGNATURE

    $24,995
    Antioch, IL

    Experience comfort,power, and reliability in thiswell-maintained, single-owner 2005Chaparral 260 Signature, powered by a MerCruiser 6.2L engine delivering 350 horsepower with appro... View Details

    View 30 Photos and Details Contact Seller
    $24,995
    VIEW DETAILS
  • 2012 Chaparral 206 SSI

    2012 Chaparral 206 SSI

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

    2012 Chaparral 206 SSI View Details

    View 30 Photos and Details Contact Seller
    $27,499
    VIEW DETAILS
  • Price Drop 2007 Chaparral 290 Signature

    2007 Chaparral 290 Signature

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

    2007 Chaparral 290 Signature | Well-Maintained Cruiser with Recent UpgradesThis 2007 Chaparral 290 Signature is a spacious, well-equipped express cruiser that has been thoughtfull... View Details

    View 40 Photos and Details Contact Seller
    $47,995
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

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

    This 2026 Chaparral will be available for purchase beginning October 1. A deposit may be placed now to reserve the boat and ensure it is yours as soon as it becomes available.The... View Details

    View 23 Photos and Details Contact Seller
    $64,995
    VIEW DETAILS
  • 2023 Chaparral SSi

    2023 Chaparral SSi

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

    Turn the key and enjoy a nearly new Chaparral without the new-boat price. This 2023 Chaparral 23 SSi has just 38.1 hours and is powered by a 250 HP MerCruiser 4.5L sterndrive, del... View Details

    View 36 Photos and Details Contact Seller
    $64,995
    VIEW DETAILS
  • 2020 Chaparral SSX

    2020 Chaparral SSX

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

    The 2020 Chaparral 257 SSX delivers the upscale styling, premium comfort, and strong performance that have made Chaparral’s SSX series a favorite among boaters looking for a refin... View Details

    View 30 Photos and Details Contact Seller
    $89,995
    VIEW DETAILS
  • 2026 Chaparral SSX

    2026 Chaparral SSX

    $224,940
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 26'
    • 2026 / New
    • $224,940

    2026 Chaparral SSX 6: Luxury Meets VersatilityExperience the gold standard of luxury bowriders with the 2026 Chaparral SSX 6. Designed for boaters who refuse to compromise between... View Details

    View 40 Photos and Details Contact Seller
    $224,940
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

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

    Chaparral 21 SSi — Compact, Sporty, and Ready for Everyday Lake AdventuresThe Chaparral 21 SSi is a small-but-mighty bowrider built for boaters who want performance, comfort, and... View Details

    View 30 Photos and Details Contact Seller
    $66,680
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

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

    Chaparral 21 SSi — Compact Bowrider, Big Impact on the WaterThe Chaparral 21 SSi is a standout for boaters who want a nimble, stylish bowrider that’s easy to handle, perfect for d... View Details

    View 28 Photos and Details Contact Seller
    $72,570
    VIEW DETAILS
  • 2021 Chaparral Surf

    2021 Chaparral Surf

    $64,995
    Oshkosh, WI

    2021 Chaparral 23 SurfTake your time on the water to the next level with this 2021 Chaparral 23 Surf. Powered by a Volvo Penta 280 V6 with only 78 hours, this versatile bowrider d... View Details

    View 37 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

    2026 Chaparral 21 SSiCompact in size, bold in spirit — the 2026 21 SSi is proof that big performance can come in a sleek, manageable package. This model in striking Atlas Blue pai... View Details

    View 27 Photos and Details Contact Seller
    $72,175
    VIEW DETAILS
  • 2026 Chaparral SSi OB

    2026 Chaparral SSi OB

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

    This 2026 Chaparral is currently being used as a dealer demo and will be available for purchase beginning October 1. A deposit may be placed now to reserve the boat and ensure it... View Details

    View 33 Photos and Details Contact Seller
    $66,995
    VIEW DETAILS
  • 2025 Chaparral SSi

    2025 Chaparral SSi

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

    This 2026 Chaparral is currently being used as a dealer demo and will be available for purchase beginning October 1. A deposit may be placed now to reserve the boat and ensure it... View Details

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

    2026 Chaparral SSX

    $225,815
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 26'
    • 2026 / New
    • $225,815

    Chaparral SSX 6 — Elevated Style, Performance, and Versatility for Every Lake DayThe 2026 Chaparral SSX 6 steps above the ordinary with bold design, premium finishes, and a layout... View Details

    View 37 Photos and Details Contact Seller
    $225,815
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

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

    This 2026 Chaparral will be available for purchase beginning October 1. A deposit may be placed now to reserve the boat and ensure it is yours as soon as it becomes available.Chap... View Details

    View 26 Photos and Details Contact Seller
    $74,995
    VIEW DETAILS
  • 2022 Chaparral SSX

    2022 Chaparral SSX

    $164,995
    Oshkosh, WI
    • Oshkosh, WI
    • Bowrider
    • 28'
    • 2022 / Used
    • $164,995

    Luxury. Performance. Presence.This 2022 Chaparral 287 SSX is the epitome of elegance on the water. With its bold styling, spacious layout, and Chaparral’s legendary ride quality,... View Details

    View 40 Photos and Details Contact Seller
    $164,995
    VIEW DETAILS
  • 2026 Chaparral SSi

    2026 Chaparral SSi

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

    The 2026 Chaparral 23 SSi delivers the perfect combination of sporty performance, premium comfort, and versatile space for unforgettable days on the water. Powered by a MerCruiser... View Details

    View 35 Photos and Details Contact Seller
    $87,195
    VIEW DETAILS
1 to 21 of 24 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.