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Chaparral Ssi boats for sale

557 Boats Available
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  1. 2025 Chaparral 19 SSi OB

    Chaparral 19 SSi OB

    2025
    Request Price

    Outboard power joins quality and style in this 19 SSi. Quick to plane, full of power, and full of all the standard features that set Chaparral apart from the rest. Storage is abundant...under the seats, in the helm, in a wakeboard sized floor locker and there's also a 30 qt cooler under the back seat. From there, you will notice the full size sun lounge for those sunny days. 

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    10
    Manufacturer Specification
  2. 2025 Chaparral 23 SSi

    Chaparral 23 SSi

    2025
    Request Price

    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 trailer, the 23 SSi's style is captivating, but its appeal is more than skin deep. Stainless steel hardware, composite seat bases, a cockpit drainage system, Extended V-Plane running surface and a vinyl wrapped dash are keeping with the Chaparral DNA. MerCruiser and Volvo power options delivers crisp low-end, controlled midrange and exciting full throttle performance. Step up to the 23 SSi and enjoy U-Shaped cockpit seating, a spacious bow, and dual direction chaise lounge.

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    10
    Manufacturer Specification
  3. 2025 Chaparral 21 SSi Ski & Fish

    Chaparral 21 SSi Ski & Fish

    2025
    Request Price

    The 21 Ski & Fish SSi combines the best of everything. Larger casting platforms, abundant storage, and flexible seating cockpit design. Options you won't want to be without include snap-in carpet, a bow walk-thru door, fish finder, upgraded dash and a swim platform logo mat. Additionally, you can upgrade either one or both of the standard bucket seats to an ultra-comfort pedestal complete with a flip-up front bolster. Anglers will love the protected rod storage, standard trolling motor and 70-quart livewell.

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    15
    Manufacturer Specification
  4. 2025 Chaparral 21 SSi Ski & Fish OB

    Chaparral 21 SSi Ski & Fish OB

    2025
    Request Price

    Valued for its versatility and innovation, the 21 SSi Outboard Ski & Fish is both a first rate fishing machine and a power packed family runabout. Removable fishing seats, an aft hinged sundeck and loads of storage space create a comfort level that is unprecedented. A Limited Lifetime Hull Warranty inspires confidence. Expert workmanship, time-tested construction and detail-minded rigging deliver years of trouble free fun. Paired with a helm design featuring a custom hand-stitched brow, our Yamaha gauge package provides real time data output at your fingertips. Aluminum faced gauges are accented with stainless steel bezels. Fog resistant and built to last, our high quality instruments are easily legible in all kind of lighting conditions.

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    13
    Manufacturer Specification
  5. 2025 Chaparral 23 SSi OB

    Chaparral 23 SSi OB

    2025
    Request Price

    The 23 SSi outboard combines everything great about the 23 SSi with the power, performance, and quality of a Yamaha Outboard. Coupled together, this makes a combination that's hard to beat. Saltwater or Freshwater, this outboard-powered 23-footer is guaranteed to impress. Quick to plane, full of power, and full of all the standard features that set Chaparral apart from the rest.

    More…
    16
    Manufacturer Specification
  6. 2025 Chaparral 21 SSi OB

    Chaparral 21 SSi OB

    2025
    Request Price

    When outboard power meets our 21 SSi, exellence awaits. Key options include snap-in cockpit carpet, a swim platform mat and a Velocity Folding Arch Tower. Abundant storage, ultra comfort seats, all paired with a premium stereo system truly redefines the standard in luxury on the water. 

    More…
    12
    Manufacturer Specification
  7. 2025 Chaparral 21 SSi

    Chaparral 21 SSi

    2025
    Request Price

    The 21 SSi's style is captivating, but its appeal is more than skin deep. Stainless steel hardware, composite seat bases, a cockpit drainage system, an Extended V-Plane running surface, and a molded fiberglass dash are keeping with the Chaparral DNA. Step up to the 21 SSI and enjoy wraparound seat backs in the bow, an anchor locker forward, and room for everyone.

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    16
    Manufacturer Specification
  8. 2025 Chaparral 21 SSi

    Chaparral 21 SSi

    Akron, Ohio
    2025
    $71,035
    Seller Boat Masters State Park
    52
    Contact
    330-574-4946
    ×
  9. 2025 Chaparral 21 SSi

    Chaparral 21 SSi

    Indianapolis, Indiana
    2025
    $61,850
    Seller Just Add Water Boats, LLC
    25
    Contact
    317-707-4286
    ×
  10. 2026 Chaparral 19 SSi OB

    Chaparral 19 SSi OB

    Indianapolis, Indiana
    2026
    $56,520
    Seller Just Add Water Boats, LLC
    21
    Contact
    317-707-4286
    ×
  11. 2026 Chaparral 21 SSI Sport

    Chaparral 21 SSI Sport

    Belle Vernon, Pennsylvania
    2026
    Request Price
    Seller Smitty's Marina
    28
    Contact
    724-414-6855
    ×
  12. 2026 Chaparral 21 SSI Sport

    Chaparral 21 SSI Sport

    Belle Vernon, Pennsylvania
    2026
    Request Price
    Seller Smitty's Marina
    26
    Contact
    724-414-6855
    ×
  13. 2026 Chaparral 21 SSI Sport

    Chaparral 21 SSI Sport

    Belle Vernon, Pennsylvania
    2026
    Request Price
    Seller Smitty's Marina
    28
    Contact
    724-414-6855
    ×
  14. 2025 Chaparral 23 SSi

    Chaparral 23 SSi

    Belle Vernon, Pennsylvania
    2025
    $93,730
    Seller Smitty's Marina
    32
    Contact
    724-414-6855
    ×
  15. 2025 Chaparral 19 SSi OB

    Chaparral 19 SSi OB

    Belle Vernon, Pennsylvania
    2025
    $51,100
    Seller Smitty's Marina
    25
    Contact
    724-414-6855
    ×
  16. 2025 Chaparral 21 SSi

    Chaparral 21 SSi

    Akron, Ohio
    2025
    $64,059
    Seller Boat Masters State Park
    30
    Contact
    330-574-4946
    ×
  17. 2025 Chaparral 23 SSI SPORT

    Chaparral 23 SSI SPORT

    Somerset, Kentucky
    2025
    $100,871
    Seller Lake Cumberland Marine
    157
    Contact
    606-332-2206
    ×

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