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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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  • 2020 Mastercraft X22

    2020 Mastercraft X22

    $99,921
    Pewaukee, WI

    2020 Mastercraft X22 Enjoy next-level wakesurfing and family fun on Pewaukee Lake with the 2020 MasterCraft X22. Powered by the Ilmor 6.0L MPI inboard engine, this boat delivers ef... View Details

    View 30 Photos and Details Contact Seller
    $99,921
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  • 2026 Mastercraft XT24

    2026 Mastercraft XT24

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • 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

    View 29 Photos and Details Contact Seller
    Call for price
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  • 2026 Mastercraft NXT22

    2026 Mastercraft NXT22

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Ski & Wake
    • 22'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft NXT 22. Fresh style and proven performance in one dialed-in package-that's the NXT22. SurfStar and ample ballast mean you get clean, consistent wav... View Details

    View 7 Photos and Details Contact Seller
    Call for price
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  • 2026 Mastercraft XT23

    2026 Mastercraft XT23

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Ski & Wake
    • 23'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft XT23. With head-turning looks, serious wave-making power, and comfort to keep everyone happy, the XT23 is built to take over the lake-not just hand... View Details

    View 25 Photos and Details Contact Seller
    Call for price
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  • 2026 Mastercraft NXT23

    2026 Mastercraft NXT23

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • 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

    View 30 Photos and Details Contact Seller
    Call for price
    VIEW DETAILS
  • 2026 Mastercraft NXT20

    2026 Mastercraft NXT20

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Ski & Wake
    • 20'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft NXT24-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 lineip with room... View Details

    View 27 Photos and Details Contact Seller
    Call for price
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  • 2026 Mastercraft XT20

    2026 Mastercraft XT20

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • 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
    Call for price
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  • 2026 Mastercraft XT22 T

    2026 Mastercraft XT22 T

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • Ski & Wake
    • 22'
    • 2026 / New
    • Call for price

    Introducing the 2026 MasterCraft XT22 T, pairing iconic style with modern muscle, delivering proven performance in a package that looks as good as it rides. With a traditional bow... View Details

    View 19 Photos and Details Contact Seller
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  • 2026 Mastercraft NXT24

    2026 Mastercraft NXT24

    Call for price
    Pewaukee, WI
    • Pewaukee, WI
    • 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

    View 30 Photos and Details Contact Seller
    Call for price
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  • 2004 Centurion AVALANCHE C4

    2004 Centurion AVALANCHE C4

    $24,995
    Pewaukee, WI

    Thie Centurion will put a smile on your face as soon as you hear the big V8 with the thru hull exhaust! Get into a great performance tow boat without breaking the bank. Come on dow... View Details

    View 24 Photos and Details Contact Seller
    $24,995
    VIEW DETAILS
  • 2022 Heyday H22

    2022 Heyday H22

    $60,136
    Pewaukee, WI

    Sale Price: $69,900 View Details

    View 24 Photos and Details Contact Seller
    $60,136
    VIEW DETAILS
  • 2015 Bryant 210

    2015 Bryant 210

    $24,839
    Pewaukee, WI
    • Pewaukee, WI
    • Bowrider
    • 21'
    • 2015 / Used
    • $24,839

    2015 Bryant 210 Experience the thrill of luxury on the water with the stunning 2015 Bryant 210, available now at SkipperBud's Pewaukee in Pewaukee, WI. Unmatched Performance Powere... View Details

    View 30 Photos and Details Contact Seller
    $24,839
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  • 2002 Crownline 202BR

    2002 Crownline 202BR

    $14,484
    Pewaukee, WI
    • Pewaukee, WI
    • Bowrider
    • 20'
    • 2002 / Used
    • $14,484

    2002 Crownline 202BR Experience the thrill of the open water with the 2002 Crownline 202BR, a stunning blend of performance and elegance. This boat is designed for those who crave... View Details

    View 30 Photos and Details Contact Seller
    $14,484
    VIEW DETAILS
  • 2020 ATX Surf Boats ATX 22

    2020 ATX Surf Boats ATX 22

    $79,995
    Pewaukee, WI

    2020 ATX Surf Boats ATX 22 View Details

    View 12 Photos and Details Contact Seller
    $79,995
    VIEW DETAILS
  • 2015 Mastercraft X20

    2015 Mastercraft X20

    $74,000
    Pewaukee, WI

    Features: Premium Audio and Touchscreen Pkg Gen2 Surf System ZFT-4 Tower w/Swivel Clamping Board Racks Hull Metal Flake JL Audio Speakers 2-ZFT-4 BTS Windshield Convertible Center... View Details

    View 30 Photos and Details Contact Seller
    $74,000
    VIEW DETAILS
  • Price Drop 2024 Cobalt R8 Outboard

    2024 Cobalt R8 Outboard

    $199,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 27'
    • 2024 / Used
    • $199,900

    See This stunning 2024 Cobalt R8 Outboard, a remarkable bowrider that combines elegance with performance. Measuring an impressive 27.83 feet in overall length, this vessel is craft... View Details

    View 48 Photos and Details Contact Seller
    $199,900
    VIEW DETAILS
  • 2016 Chaparral 307 SSX

    2016 Chaparral 307 SSX

    $129,900
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 30'
    • 2016 / Used
    • $129,900

    Meet your next on-the-water obsession: the 2016 Chaparral 307 SSX  a head turning mix of luxury, performance, and pure boating bliss! At 30 feet, she delivers a ride as smooth as s... View Details

    View 48 Photos and Details Contact Seller
    $129,900
    VIEW DETAILS
  • 2019 Formula 350 Crossover Bowrider

    2019 Formula 350 Crossover Bowrider

    $325,000
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 35'
    • 2019 / Used
    • $325,000

    See this Gorgeous fresh-water Formula 350 CBR with just 140 engine hours! Recent price reduction. Ready to go boating now. The 350 CBR offers an ideal combination of luxurious cock... View Details

    View 53 Photos and Details Contact Seller
    $325,000
    VIEW DETAILS
  • 2026 Chaparral 23 SSi

    2026 Chaparral 23 SSi

    $89,259
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 23'
    • 2026 / New
    • $89,259

    Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 23 SSi. With a ChaparralONE price including the tr... View Details

    View 44 Photos and Details Contact Seller
    $89,259
    VIEW DETAILS
  • 2026 Chaparral 21 SSi OB

    2026 Chaparral 21 SSi OB

    $75,794
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 21'
    • 2026 / New
    • $75,794

    Now on display, see this new 2026 Chaparral 21 SSi powered by a hearty 200 HP Yamaha 4-stroke outboard. Chaparral's innovative use of space means an abundance of cockpit space, sto... View Details

    View 26 Photos and Details Contact Seller
    $75,794
    VIEW DETAILS
  • Price Drop 2014 Chaparral 287 SSX

    2014 Chaparral 287 SSX

    $69,600
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 28'
    • 2014 / Used
    • $69,600

    Sharp, powerful Chaparral 287 SSX. Includes Volvo Penta 430 HP V-8 with DTS. Just 260 engine hours. Don’t miss out on this nicely maintained Chaparral 287 SSX. This 9-foot beam bo... View Details

    View 31 Photos and Details Contact Seller
    $69,600
    VIEW DETAILS
Showing 127 to 147 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.