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Cobra Python, Chaparral 21 Ssi Sloop boats for sale

Clear All pythonChaparral 21-ssi power-sloop power-runabout power-unspec power-pwc
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326 more Makes...
Chaparral Models
  • 23 SSi
  • 21 SSi
  • 21 SSi OB
  • 247 SSX
  • 267 SSX
  • 23 SSi OB
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    83 boats
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      2026 Chaparral 21 SSi OB

      $75,369

      $561/mo*

      Bluffton, SC 29910 | Longshore Boats

      • 2026 Chaparral 21 SSi OB
      • 2026 Chaparral 21 SSi OB
      • 2026 Chaparral 21 SSi OB
      • 2026 Chaparral 21 SSi OB
      Dealer Logo

      2026 Chaparral 21 SSi

      Request a Price

      Hayden, ID 83835 | Tobler Marina

      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      Dealer Logo

      2026 Chaparral 21 SSi

      $74,495

      $555/mo*

      Delavan, WI 53115 | Reed's Marine

      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      Dealer Logo

      2021 Chaparral 21 SSi

      $49,850

      $434/mo*

      Green Bay, WI 54173 | Marine 365

      • 2021 Chaparral 21 SSi
      • 2021 Chaparral 21 SSi
      • 2021 Chaparral 21 SSi
      • 2021 Chaparral 21 SSi

      2025 Chaparral 21 SSi

      $73,785

      $550/mo*

      Lewisville, TX 75067 | Jerry Whittle Boats

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

      2025 Chaparral 21 SSi

      $75,020

      $559/mo*

      Kenmore, WA 98028 | Seattle Water Sports

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

      2026 Chaparral 21 SSi

      $75,965

      $566/mo*

      Galena, MD 21635 | Jim's Marine, Inc.

      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi

      2026 Chaparral 21 SSi

      $74,975

      $559/mo*

      Kenmore, WA 98028 | Seattle Water Sports

      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2026 Chaparral 21 SSi
      • 2025 Chaparral 21 SSi

        $64,085

        $477/mo*

        Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

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

        2026 Chaparral 21 SSi OB

        $69,335

        $517/mo*

        Stevensville, MD 21666 | Jim's Marine, Inc.

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

        2026 Chaparral 21 SSi

        $72,485

        $540/mo*

        Lake Hopatcong, NJ 07849 | Prospect Point Boat Yards

        • 2026 Chaparral 21 SSi
        • 2026 Chaparral 21 SSi
        • 2026 Chaparral 21 SSi
        • 2026 Chaparral 21 SSi

        2025 Chaparral 21 SSi

        $74,290

        $553/mo*

        Kenmore, WA 98028 | Seattle Water Sports

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

        2025 Chaparral 21 SSi

        $68,875

        $513/mo*

        Walworth, WI 53184 | Munson Ski & Marine - Fontana

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

        2025 Chaparral 21 SSi

        $68,875

        $513/mo*

        Walworth, WI 53184 | Munson Ski & Marine - Fontana

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

        2026 Chaparral 21 SSi OB

        $75,369

        $561/mo*

        Bluffton, SC 29910 | Longshore Boats

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

          Request a Price

          Hayden, ID 83835 | Tobler Marina

          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi

          2026 Chaparral 21 SSi

          $74,495

          $555/mo*

          Delavan, WI 53115 | Reed's Marine

          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi

          2026 Chaparral 21 SSi

          $73,360

          $547/mo*

          Delavan, WI 53115 | Reed's Marine

          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi

          2025 Chaparral 21 SSi

          $67,995

          $507/mo*

          Round Lake, IL 60073 | Munson Ski & Marine

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

          2025 Chaparral 21 SSi

          $68,875

          $513/mo*

          Round Lake, IL 60073 | Munson Ski & Marine

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

          2026 Chaparral 21 SSi

          $71,700

          $534/mo*

          Galena, MD 21635 | Jim's Marine, Inc.

          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi
          • 2026 Chaparral 21 SSi

          2025 Chaparral 21 SSi

          $68,875

          $513/mo*

          Round Lake, IL 60073 | Munson Ski & Marine

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

          2026 Chaparral 21 SSi

          $75,970

          $566/mo*

          Suamico, WI 54173 | Marine 365

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

            $69,335

            $517/mo*

            Wilmington, DE 19801 | Jim's Marine, Inc.

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

            2025 Chaparral 21 SSi OB

            $79,850

            $595/mo*

            Green Bay, WI 54173 | Marine 365

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

            2026 Chaparral 21 SSi OB

            $68,425

            $510/mo*

            Wilmington, DE 19801 | Jim's Marine, Inc.

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

              Request a Price

              Hayden, ID 83835 | Tobler Marina

              • 2026 Chaparral 21 SSi
              • 2026 Chaparral 21 SSi
              • 2026 Chaparral 21 SSi
              • 2026 Chaparral 21 SSi

              2025 Chaparral 21 SSi OB

              Request a Price

              Galena, MD 21635 | Jim's Marine, Inc.

              • 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

                Request a Price

                Hayden, ID 83835 | Tobler Marina

                • 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

                Request a Price

                Galena, MD 21635 | Jim's Marine, Inc.

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

                  $69,930

                  $521/mo*

                  Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

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

                    $70,205

                    $523/mo*

                    Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

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

                    2025 Chaparral 21 SSi OB

                    $76,480

                    $570/mo*

                    Lake Hopatcong, NJ 07849 | Prospect Point Boat Yards

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

                    2025 Chaparral 21 SSi Ski & Fish OB

                    $75,095

                    $559/mo*

                    Lake Hopatcong, NJ 07849 | Prospect Point Boat Yards

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