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Cobra Python, Chaparral Ski and Wakeboard boats for sale

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248 more Makes...
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62 more Models...
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    273 boats
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      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
      Dealer Logo

      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
      Dealer Logo

      2014 Chaparral Sunesta 224

      $42,995

      $374/mo*

      Marrero, LA 70072 | The Boat Yard, Inc

      • 2014 Chaparral Sunesta 224
      • 2014 Chaparral Sunesta 224
      • 2014 Chaparral Sunesta 224
      • 2014 Chaparral Sunesta 224
      Dealer Logo

      2025 Chaparral 21 Surf

      $89,960

      $670/mo*

      Nashville, IL 62263 | Yachts to Sea

      • 2025 Chaparral 21 Surf
      • 2025 Chaparral 21 Surf
      • 2025 Chaparral 21 Surf
      • 2025 Chaparral 21 Surf
      • 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

        2024 Chaparral 19 SSi OB

        $49,900

        $434/mo*

        Sarasota, FL 34243 | Erickson Marine Corp.

        • 2024 Chaparral 19 SSi OB
        • 2024 Chaparral 19 SSi OB
        • 2024 Chaparral 19 SSi OB
        • 2024 Chaparral 19 SSi OB
        • 2007 Chaparral 256 SSi

          $34,000

          $296/mo*

          Saint Augustine, FL 32084 | Admiral Yacht Sales

          • 2007 Chaparral 256 SSi
          • 2007 Chaparral 256 SSi
          • 2007 Chaparral 256 SSi
          • 2007 Chaparral 256 SSi

          2013 Chaparral 257 SSX

          $38,995

          $339/mo*

          Williamstown, NJ 08094 | Cecil Marine

          • 2013 Chaparral 257 SSX
          • 2013 Chaparral 257 SSX
          • 2013 Chaparral 257 SSX
          • 2013 Chaparral 257 SSX

          2025 Chaparral 26 Surf

          Request a Price

          Nashville, IL 62263 | Yachts to Sea

          • 2025 Chaparral 26 Surf
          • 2025 Chaparral 26 Surf
          • 2025 Chaparral 26 Surf
          • 2025 Chaparral 26 Surf

          2023 Chaparral 21 SSi OB

          $58,995

          $440/mo*

          Williamstown, NJ 08094 | Cecil Marine

          • 2023 Chaparral 21 SSi OB
          • 2023 Chaparral 21 SSi OB
          • 2023 Chaparral 21 SSi OB
          • 2023 Chaparral 21 SSi OB
          • 2024 Chaparral 23 Surf

            $85,900

            $640/mo*

            Gilford, NH 03249 | Silver Sands Marina

            • 2024 Chaparral 23 Surf
            • 2024 Chaparral 23 Surf
            • 2024 Chaparral 23 Surf
            • 2024 Chaparral 23 Surf

            2020 Chaparral 297 SSX

            $100,000

            $745/mo*

            Southold, NY 11971 | Albertson Marine

            • 2020 Chaparral 297 SSX
            • 2020 Chaparral 297 SSX
            • 2020 Chaparral 297 SSX
            • 2020 Chaparral 297 SSX

            2014 Chaparral 21 H2O Sport

            $21,995

            Williamstown, NJ 08094 | Cecil Marine

            • 2014 Chaparral 21 H2O Sport
            • 2014 Chaparral 21 H2O Sport
            • 2014 Chaparral 21 H2O Sport
            • 2014 Chaparral 21 H2O Sport

            2017 Chaparral Vortex 243 VRX

            $48,995

            $427/mo*

            Evansville, IN 47714 | East Side Marine

            • 2017 Chaparral Vortex 243 VRX
            • 2017 Chaparral Vortex 243 VRX
            • 2017 Chaparral Vortex 243 VRX
            • 2017 Chaparral Vortex 243 VRX
            • 2024 Chaparral 26 Surf

              $157,500

              $1,173/mo*

              Tafton, PA 18464 | The Boat Shop

              • 2024 Chaparral 26 Surf
              • 2024 Chaparral 26 Surf
              • 2024 Chaparral 26 Surf
              • 2024 Chaparral 26 Surf

              2019 Chaparral 246 SSi

              $59,900

              $446/mo*

              Williamstown, NJ 08094 | Cecil Marine

              • 2019 Chaparral 246 SSi
              • 2019 Chaparral 246 SSi
              • 2019 Chaparral 246 SSi
              • 2019 Chaparral 246 SSi
              • 2026 Chaparral 23 SSi

                $89,394

                $666/mo*

                Richmond, VA 23237 | Nautical Marine Inc.

                2026 Chaparral 23 SSi

                2025 Chaparral 21 SSi OB

                $50,000

                $372/mo*

                Charleston, WV 25303 | Trojan Landing Marine

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

                2025 Chaparral 23 SSi OB

                $80,000

                $596/mo*

                Charleston, WV 25303 | Trojan Landing Marine

                • 2025 Chaparral 23 SSi OB
                • 2025 Chaparral 23 SSi OB
                • 2025 Chaparral 23 SSi OB
                • 2025 Chaparral 23 SSi OB

                2009 Chaparral 276 SSX

                $49,999

                $435/mo*

                Seminole, FL 33772 | USA Coastal Marine

                • 2009 Chaparral 276 SSX
                • 2009 Chaparral 276 SSX
                • 2009 Chaparral 276 SSX
                • 2009 Chaparral 276 SSX
                • 2026 Chaparral 250 OSX

                  Request a Price

                  Richmond, VA 23237 | Nautical Marine Inc.

                  • 2026 Chaparral 250 OSX
                  • 2026 Chaparral 250 OSX
                  • 2026 Chaparral 250 OSX
                  • 2026 Chaparral 250 OSX
                  • 2006 Chaparral 236 SSi

                    $27,900

                    $243/mo*

                    Pensacola, FL 32501 | At Ease Yacht Sales

                    • 2006 Chaparral 236 SSi
                    • 2006 Chaparral 236 SSi
                    • 2006 Chaparral 236 SSi
                    • 2006 Chaparral 236 SSi
                    • 2013 Chaparral 224 Xtreme

                      $59,500

                      $443/mo*

                      Big Sandy, TN 38221 | New Anchor Yacht Sales

                      • 2013 Chaparral 224 Xtreme
                      • 2013 Chaparral 224 Xtreme
                      • 2013 Chaparral 224 Xtreme
                      • 2013 Chaparral 224 Xtreme
                      • 2023 Chaparral 28 Surf

                        Request a Price

                        Rogers, MN 72756 | MarineMax

                        • 2023 Chaparral 28 Surf
                        • 2023 Chaparral 28 Surf
                        • 2023 Chaparral 28 Surf
                        • 2023 Chaparral 28 Surf
                          • 2007 Chaparral 276 SSX

                            $37,500

                            $326/mo*

                            Pensacola, FL 32507 | At Ease Yacht Sales

                            • 2007 Chaparral 276 SSX
                            • 2007 Chaparral 276 SSX
                            • 2007 Chaparral 276 SSX
                            • 2007 Chaparral 276 SSX
                            • 2026 Chaparral 21 SSi OB

                              $67,995

                              $507/mo*

                              Richmond, VA 23237 | Nautical Marine Inc.

                              2026 Chaparral 21 SSi OB

                              2016 Chaparral 21 H2O Sport

                              $27,500

                              $239/mo*

                              Williamstown, NJ 08094 | Cecil Marine

                              • 2016 Chaparral 21 H2O Sport
                              • 2016 Chaparral 21 H2O Sport
                              • 2016 Chaparral 21 H2O Sport
                              • 2016 Chaparral 21 H2O Sport
                              • 2023 Chaparral 26 Surf

                                Request a Price

                                Rogers, MN 72756 | MarineMax

                                • 2023 Chaparral 26 Surf
                                • 2023 Chaparral 26 Surf
                                • 2023 Chaparral 26 Surf
                                • 2023 Chaparral 26 Surf
                                  • 2026 Chaparral 21 SSi

                                    $68,780

                                    $512/mo*

                                    Richmond, VA 23237 | Nautical Marine Inc.

                                    2026 Chaparral 21 SSi
                                    • 2023 Chaparral 30 Surf

                                      Request a Price

                                      Rogers, MN 72756 | MarineMax

                                      • 2023 Chaparral 30 Surf
                                      • 2023 Chaparral 30 Surf
                                      • 2023 Chaparral 30 Surf
                                      • 2023 Chaparral 30 Surf

                                        2024 Chaparral 21 SSi OB

                                        $58,995

                                        $440/mo*

                                        Williamstown, NJ 08094 | Cecil Marine

                                        • 2024 Chaparral 21 SSi OB
                                        • 2024 Chaparral 21 SSi OB
                                        • 2024 Chaparral 21 SSi OB
                                        • 2024 Chaparral 21 SSi OB
                                        • 2023 Chaparral 30 Surf

                                          $165,900

                                          $1,236/mo*

                                          Sunrise Beach, MO 65079 | Heartland Marine

                                          • 2023 Chaparral 30 Surf
                                          • 2023 Chaparral 30 Surf
                                          • 2023 Chaparral 30 Surf
                                          • 2023 Chaparral 30 Surf

                                          2008 Chaparral 256 SSi

                                          $39,900

                                          $347/mo*

                                          Williamstown, NJ 08094 | Cecil Marine

                                          • 2008 Chaparral 256 SSi
                                          • 2008 Chaparral 256 SSi
                                          • 2008 Chaparral 256 SSi
                                          • 2008 Chaparral 256 SSi
                                          • 2015 Chaparral Sunesta 264 ProXtreme

                                            $69,999

                                            $521/mo*

                                            Smithtown, NY 11787 | Knot 10 Yacht Sales

                                            • 2015 Chaparral Sunesta 264 ProXtreme
                                            • 2015 Chaparral Sunesta 264 ProXtreme
                                            • 2015 Chaparral Sunesta 264 ProXtreme
                                            • 2015 Chaparral Sunesta 264 ProXtreme
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