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New Cobra Python, Chaparral 21 Ssi Ob Ski and Wakeboard boats for sale

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108 more Makes...
Chaparral Ranges
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Chaparral Models
  • 21 SSi
  • 21 Surf
  • 23 SSi
  • 23 Surf
  • 21 SSi OB
  • 26 Surf
  • 270 OSX
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  • 267 SSX
  • 28 Surf
  • 19 SSi OB
  • 21 SSi Ski & Fish
  • 21 SSi Ski & Fish OB
  • 23 SSi OB
  • 250 OSX
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  • 2870 SSX
  • 30 Surf
  • 307 SSX
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    11 boats
    Sort: Recommended
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    • Price: High to Low
    • Price: Low to High

      2025 Chaparral 21 SSi OB

      $72,635

      $541/mo*

      Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

      • 2025 Chaparral 21 SSi OB
      • 2025 Chaparral 21 SSi OB
      • 2025 Chaparral 21 SSi OB
      • 2025 Chaparral 21 SSi OB
      Dealer Logo

      2026 Chaparral 21 SSi Ski & Fish OB

      $87,060

      $649/mo*

      Kenmore, WA 98028 | Seattle Water Sports

      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB
      Dealer Logo

      2024 Chaparral 21 SSI FISH & SKI OB

      $69,435

      $517/mo*

      Sodus Point, NY 14555 | Krenzer Marine

      • 2024 Chaparral 21 SSI FISH & SKI OB
      • 2024 Chaparral 21 SSI FISH & SKI OB
      • 2024 Chaparral 21 SSI FISH & SKI OB
      • 2024 Chaparral 21 SSI FISH & SKI OB
      Dealer Logo

      2025 Chaparral 21 SSi OB

      $76,855

      $573/mo*

      Kenmore, WA 98028 | Seattle Water Sports

      • 2025 Chaparral 21 SSi OB
      • 2025 Chaparral 21 SSi OB
      • 2025 Chaparral 21 SSi OB
      • 2025 Chaparral 21 SSi OB

      2026 Chaparral 21 SSi Ski & Fish OB

      $87,060

      $649/mo*

      Kenmore, WA 98028 | Seattle Water Sports

      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB
      • 2026 Chaparral 21 SSi Ski & Fish OB

        $106,833

        $796/mo*

        Somerset, KY 42503 | Lake Cumberland Marine

        • 2026 Chaparral 21 SSi Ski & Fish OB
        • 2026 Chaparral 21 SSi Ski & Fish OB
        • 2026 Chaparral 21 SSi Ski & Fish OB
        • 2026 Chaparral 21 SSi Ski & Fish OB
        • 2025 Chaparral 21 SSi OB

          $72,635

          $541/mo*

          Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB

          2025 Chaparral 21 SSi OB

          $68,540

          $511/mo*

          Longs, SC 29568 | Sportsman's Choice Marine

          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB

          2024 Chaparral 21 SSI FISH & SKI OB

          $69,435

          $517/mo*

          Sodus Point, NY 14555 | Krenzer Marine

          • 2024 Chaparral 21 SSI FISH & SKI OB
          • 2024 Chaparral 21 SSI FISH & SKI OB
          • 2024 Chaparral 21 SSI FISH & SKI OB
          • 2024 Chaparral 21 SSI FISH & SKI OB

          2025 Chaparral 21 SSi OB

          $69,995

          $521/mo*

          Williamstown, NJ 08094 | Cecil Marine

          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB

          2025 Chaparral 21 SSi OB

          $69,995

          $521/mo*

          Williamstown, NJ 08094 | Cecil Marine

          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB

          2025 Chaparral 21 SSi OB

          $69,995

          $521/mo*

          Williamstown, NJ 08094 | Cecil Marine

          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2025 Chaparral 21 SSi OB
          • 2024 Chaparral 21 SSi OB

            $64,950

            $484/mo*

            Sarasota, FL 34243 | Erickson Marine Corp.

            • 2024 Chaparral 21 SSi OB
            • 2024 Chaparral 21 SSi OB
            • 2024 Chaparral 21 SSi OB
            • 2024 Chaparral 21 SSi OB
            • 2026 Chaparral 21 SSi OB

              $67,995

              $507/mo*

              Richmond, VA 23237 | Nautical Marine Inc.

              2026 Chaparral 21 SSi OB
              • 2026 Chaparral 21 SSi Ski & Fish OB

                $106,833

                $796/mo*

                Somerset, KY 42503 | Lake Cumberland Marine

                • 2026 Chaparral 21 SSi Ski & Fish OB
                • 2026 Chaparral 21 SSi Ski & Fish OB
                • 2026 Chaparral 21 SSi Ski & Fish OB
                • 2026 Chaparral 21 SSi Ski & Fish OB
                Dealer Logo
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