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  • Bowrider
    Ski & Wake
    Within 100 Miles Of
    Winthrop Harbor, Illinois

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Bowrider, Ski & Wake boats for sale in Winthrop Harbor Illinois

There are 181 new and used Bowrider, Ski & Wake boats for sale in Winthrop Harbor, Illinois. Explore Bowrider and Ski & Wake brands like Tige, Aviara, Mastercraft, Cobalt, Sea Ray, and Malibu on BoatCrazy. View a wide selection of Bowrider, Ski & Wake boats from $7,900 to $585,211.
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  • Boats
  • Bowrider
    Ski & Wake
    Within 100 Miles Of
    Winthrop Harbor, Illinois
181 boats found within 100 miles from Winthrop Harbor, Illinois
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  • 2026 Mastercraft XT20

    2026 Mastercraft XT20

    Call for price
    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 20'
    • 2026 / New
    • Call for price

    Introducing the 2026 Mastercraft XT20. At 20 feet, the XT20 is compact and garage-friendly-but still delivers everything you'd expect from a MasterCraft: SurfStar performance, prem... View Details

    View 24 Photos and Details Contact Seller
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  • 2026 Mastercraft NXT23

    2026 Mastercraft NXT23

    Call for price
    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 23'
    • 2026 / New
    • Call for price

    Introducing the 2026 Mastercraft NXT23. Built to keep things simple-without sacrificing an ounce of performance. With SurfStar and ample ballast, the NXT23 delivers clean, consiste... View Details

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  • 2026 Mastercraft NXT24

    2026 Mastercraft NXT24

    Call for price
    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 24'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft NXT24. It is the biggest and boldest in the NXT family, now with standout style and thoughtful upgrades throughout. Premium vinyl pleating, powder-... View Details

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  • 2026 Mastercraft XT24

    2026 Mastercraft XT24

    Call for price
    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 24'
    • 2026 / New
    • Call for price

    The 2026 MasterCraft XT24-big, bold, and built to deliver-waves, comfort, and style all in one serious package. At 24 feet, it's the largest in the XT lineup with room for 17 and 3... View Details

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  • 2025 Aviara AV36 Outboard

    2025 Aviara AV36 Outboard

    Call for price
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 39'
    • 2025 / New
    • Call for price

    Luxury Redefined: 2025 Aviara AV36 Outboard Sleek Elegance and Unmatched Performance Experience the pinnacle of luxury boating with the Aviara AV36 Outboard. The cutting-edge desig... View Details

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  • 2025 Aviara AV40

    2025 Aviara AV40

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    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 41'
    • 2025 / New
    • Call for price

    Experience Luxury on Water with the 2025 Aviara AV40 Step into the future of boating with the Aviara AV40, a masterpiece of design and performance. This sleek vessel is the perfect... View Details

    View 19 Photos and Details Contact Seller
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  • 2025 Aviara AV40 Outboard

    2025 Aviara AV40 Outboard

    Call for price
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 42'
    • 2025 / New
    • Call for price

    2025 Aviara AV40 Outboard Experience the epitome of luxury and performance with the 2025 Aviara AV40 Outboard. Crafted with meticulous attention to detail, this stunning vessel is... View Details

    View 17 Photos and Details Contact Seller
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  • 2025 Aviara AV36

    2025 Aviara AV36

    Call for price
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 37'
    • 2025 / New
    • Call for price

    Introducing the 2025 Aviara AV36: Experience the ultimate luxury on water with the Aviara AV36, a masterpiece of design and performance. Luxurious Craftsmanship: An exquisite blend... View Details

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  • 2025 Aviara AV32 Outboard

    2025 Aviara AV32 Outboard

    Call for price
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 34'
    • 2025 / New
    • Call for price

    Experience Luxury with the 2025 Aviara AV32 Outboard Step aboard the epitome of sophistication and performance with the 2025 Aviara AV32 Outboard. Crafted to perfection by Aviara,... View Details

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  • Price Drop 2004 Malibu SUNSCAPE 23 LSV

    2004 Malibu SUNSCAPE 23 LSV

    $27,251
    Antioch, IL

    2004 Malibu SUNSCAPE 23LSV Discover the thrill of owning the stunning 2004 Malibu SUNSCAPE 23LSV, available now at SkipperBud's Antioch in Antioch, IL. This exquisite vessel embodi... View Details

    View 30 Photos and Details Contact Seller
    $27,251
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  • 2026 Sea Ray SLX 260 Surf

    2026 Sea Ray SLX 260 Surf

    Call for price
    Antioch, IL
    • Antioch, IL
    • Ski & Wake
    • 26'
    • 2026 / New
    • Call for price

    Introducing the SLX 260 Surf. Discover the SLX 260 Surf, where luxury meets innovation in wakesurfing technology. This exceptional boat combines the elegance of the SLX 260 with cu... View Details

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  • 2019 Bayliner VR5

    2019 Bayliner VR5

    $27,778
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 20'
    • 2019 / Used
    • $27,778

    2019 Bayliner VR5 Experience the thrill of the open water with the 2019 Bayliner VR5, a perfect blend of performance and elegance. This luxury boat is designed for the discerning b... View Details

    View 23 Photos and Details Contact Seller
    $27,778
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  • 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

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    $135,761
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  • 2017 Chaparral 257 SSX

    2017 Chaparral 257 SSX

    $80,000
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 25'
    • 2017 / Used
    • $80,000

    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
    $80,000
    VIEW DETAILS
  • 2005 Glastron GX 235

    2005 Glastron GX 235

    $17,452
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 23'
    • 2005 / Used
    • $17,452

    2005 Glastron GX 235: The Perfect Blend of Luxury and Performance ­ Discover the joy of boating with the 2005 Glastron GX 235, a vessel that perfectly merges luxury and exhilaratin... View Details

    View 25 Photos and Details Contact Seller
    $17,452
    VIEW DETAILS
  • 2003 Mastercraft X2

    2003 Mastercraft X2

    $14,995
    Antioch, IL

    The 2003 MasterCraft X2 is a proven classic in the world of watersports, offering a perfect balance of performance, reliability, and versatility. Powered by the Indmar 5.7L motor,... View Details

    View 29 Photos and Details Contact Seller
    $14,995
    VIEW DETAILS
  • 2017 Chaparral VORTEX 223 VR

    2017 Chaparral VORTEX 223 VR

    $39,995
    Antioch, IL

    2017 Chaparral Vortex 223 VR - Twin Rotax Power,Low Hours! Turnheads on the water with this stunning Chaparral Vortex 223 VR, powered by twin Rotax 4-TEC supercharged 200HP jet eng... View Details

    View 17 Photos and Details Contact Seller
    $39,995
    VIEW DETAILS
  • 2009 Monterey 194 FS

    2009 Monterey 194 FS

    $14,995
    Antioch, IL
    • Antioch, IL
    • Bowrider
    • 19'
    • 2009 / Used
    • $14,995

    Enjoy performance and style with this well-kept 2009 Monterey 194FS. Powered by a MerCruiser 4.3L V6 with 368 hours, this 19’ bowrider delivers smooth handling, quick acceleration,... View Details

    View 30 Photos and Details Contact Seller
    $14,995
    VIEW DETAILS
  • 2023 Monterey M20

    2023 Monterey M20

    $67,900
    Mundelein, IL
    • Mundelein, IL
    • Bowrider
    • 20'
    • 2023 / Used
    • $67,900

    Stock #482891 Video of this vessel available at www [dot] popsells [dot] com/view/482891 Reason for selling is "Relocating". This Monterey has been on the market for more than 3... View Details

    View 10 Photos and Details Contact Seller
    $67,900
    VIEW DETAILS
  • Price Drop 2021 Malibu 22 LSV

    2021 Malibu 22 LSV

    $109,000
    Barrington, IL
    • Barrington, IL
    • Ski & Wake
    • 22'
    • 2021 / Used
    • $109,000

    Stock #342618 Video of this vessel available at www [dot] popsells [dot] com/view/342618 Reason for selling is "No longer uses it.". ANY and ALL offers will be put in front of o... View Details

    View 10 Photos and Details Contact Seller
    $109,000
    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". This Chaparral has now been on the market... View Details

    View 10 Photos and Details Contact Seller
    $39,995
    VIEW DETAILS
Showing 43 to 63 of 181 boats found.
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Ski & Wake Boats on Boatcrazy

Ski & Wake boats are purpose-built for watersports enthusiasts who crave precision, performance, and fun on the water. Whether you're carving perfect slalom turns or launching wakeboard tricks, these boats are engineered to deliver the ideal pull and wave shape for each sport. With inboard or V-drive propulsion, integrated ballast systems, and wake-shaping technologies, Ski & Wake boats create custom wakes for every rider’s style and skill level.

Many models feature tower mounts, rear-facing seating, premium sound systems, and touchscreen control panels to dial in the experience. Whether you're into waterskiing, wakeboarding, or wakesurfing, these Ski & Wake boats offer a smooth ride, fast acceleration, and rider-focused features that maximize time on the water.

Browse our selection of new and used Ski & Wake boats from top tow-sport brands. Whether you're a tournament competitor or a weekend thrill-seeker, these boats are built to ride.

Ski & Wake Boats manufacturers on Boatcrazy

When looking to buy a quality Ski or Wake boat, consider these top Ski or Wake Manufacturers:

Malibu, MasterCraft, Nautique, Tige, Supra, Moomba, Axis, Heyday, Chaparral, ATX, Scarab.

Ski & Wake Boats For Sale by State

Ski & Wake Boats Frequently Asked Questions

Ski & Wake boats are built for fun on the water. They offer powerful towing capabilities for water sports and have features like ballast systems and wake-shaping technology for a customized ride. They're also spacious enough for groups and family outings.

These Ski & Wake boats can be on the higher end due to their performance features. Entry-level models can start around $90k, but fully loaded wake boats can easily exceed $200k depending on size, engine, and technology.

While they’re not designed for fishing, it’s still possible on calmer days. However, these boats are optimized for towing, and fishing-focused features like rod holders and livewells are not standard.

Yes! With more families and thrill-seekers looking to get into wake sports, Ski & Wake boats have become a popular category on Boatcrazy.com with a wide range of options for every budget and style.

Prices vary widely. Pre-owned Ski & Wake boats start around $40k–$60k, while new high-end models can run $150k to over $250k. Financing is commonly available.

Most Ski & Wake boats run between 35–45 MPH. While speed is important, they’re really optimized for creating the ideal wake, not racing.