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Used Cobra Python, Chaparral Ski and Wakeboard boats for sale

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97 more Makes...
Chaparral Models
  • 21 Surf
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    29 boats
    Sort: Recommended
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    • Price: High to Low
    • Price: Low to High

      2025 Chaparral 21 Surf

      $72,990

      $544/mo*

      Woodinville, WA 98072 | Carefree Boat Club Seattle

      • 2025 Chaparral 21 Surf
      • 2025 Chaparral 21 Surf
      • 2025 Chaparral 21 Surf
      • 2025 Chaparral 21 Surf
      Dealer Logo

      2022 Chaparral 21 Surf

      $64,999

      $484/mo*

      Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

      • 2022 Chaparral 21 Surf
      • 2022 Chaparral 21 Surf
      • 2022 Chaparral 21 Surf
      • 2022 Chaparral 21 Surf
      Dealer Logo

      2022 Chaparral 21 Surf

      $57,800

      $431/mo*

      Fort Worth, TX | North Texas Marine- Fort Worth

      • 2022 Chaparral 21 Surf
      • 2022 Chaparral 21 Surf
      • 2022 Chaparral 21 Surf
      • 2022 Chaparral 21 Surf
      Dealer Logo
      • 2019 Chaparral 21 H2O Surf

        $52,500

        $391/mo*

        Flint, TX 75762 | Private Seller

        • 2019 Chaparral 21 H2O Surf
        • 2019 Chaparral 21 H2O Surf
        • 2019 Chaparral 21 H2O Surf
        • 2019 Chaparral 21 H2O Surf
        • 2017 Chaparral 227 SSX Surf

          $59,500

          $443/mo*

          Brentwood, TN 37027 | Private Seller

          • 2017 Chaparral 227 SSX Surf
          • 2017 Chaparral 227 SSX Surf
          • 2017 Chaparral 227 SSX Surf
          • 2017 Chaparral 227 SSX Surf

          2021 Chaparral 30 Surf

          $130,000

          $968/mo*

          Miami Beach, FL 33130 | POWERBOATS USA

          • 2021 Chaparral 30 Surf
          • 2021 Chaparral 30 Surf
          • 2021 Chaparral 30 Surf
          • 2021 Chaparral 30 Surf

          2025 Chaparral 21 Surf

          $72,990

          $544/mo*

          Woodinville, WA 98072 | Carefree Boat Club Seattle

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

          2022 Chaparral 23 Surf

          $74,900

          ↓ Price Drop

          $558/mo*

          Smithville, TN 37166 | Private Seller

          • 2022 Chaparral 23 Surf
          • 2022 Chaparral 23 Surf
          • 2022 Chaparral 23 Surf
          • 2022 Chaparral 23 Surf

          2019 Chaparral 23 H2O Surf

          $69,995

          $521/mo*

          Kenmore, WA 98028 | Seattle Water Sports

          • 2019 Chaparral 23 H2O Surf
          • 2019 Chaparral 23 H2O Surf
          • 2019 Chaparral 23 H2O Surf
          • 2019 Chaparral 23 H2O Surf

          2024 Chaparral 30 Surf

          $199,450

          $1,486/mo*

          Round Lake, IL 60073 | Munson Ski & Marine

          • 2024 Chaparral 30 Surf
          • 2024 Chaparral 30 Surf
          • 2024 Chaparral 30 Surf
          • 2024 Chaparral 30 Surf

          2022 Chaparral 23 Surf

          $99,999

          $745/mo*

          Glasgow, VA 24555 | Engel Volkers Yachting Americas

          • 2022 Chaparral 23 Surf
          • 2022 Chaparral 23 Surf
          • 2022 Chaparral 23 Surf
          • 2022 Chaparral 23 Surf
          • 2021 Chaparral 30 Surf

            $159,000

            $1,185/mo*

            Charleston, SC 29492 | Longshore Boats

            • 2021 Chaparral 30 Surf
            • 2021 Chaparral 30 Surf
            • 2021 Chaparral 30 Surf
            • 2021 Chaparral 30 Surf
            • 2022 Chaparral 21 Surf

              $64,999

              $484/mo*

              Sherrills Ford, NC 28673 | Boat Rack Chaparral Boat Showroom

              • 2022 Chaparral 21 Surf
              • 2022 Chaparral 21 Surf
              • 2022 Chaparral 21 Surf
              • 2022 Chaparral 21 Surf
              • 2025 Chaparral 28 Surf

                $219,999

                $1,639/mo*

                Somerset, KY 42503 | Lake Cumberland Marine

                • 2025 Chaparral 28 Surf
                • 2025 Chaparral 28 Surf
                • 2025 Chaparral 28 Surf
                • 2025 Chaparral 28 Surf
                • 2021 Chaparral 21 Surf

                  $56,000

                  $417/mo*

                  Randolph, WI 53956 | Private Seller

                  • 2021 Chaparral 21 Surf
                  • 2021 Chaparral 21 Surf
                  • 2021 Chaparral 21 Surf
                  • 2021 Chaparral 21 Surf

                  2020 Chaparral 21 Surf

                  $58,900

                  $439/mo*

                  Somerset, KY 42501 | Coast To Coast Marine

                  • 2020 Chaparral 21 Surf
                  • 2020 Chaparral 21 Surf
                  • 2020 Chaparral 21 Surf
                  • 2020 Chaparral 21 Surf
                  • 2019 Chaparral 21 H2O Surf

                    $59,995

                    $447/mo*

                    Williams Bay, WI 53191 | Gage Marine

                    • 2019 Chaparral 21 H2O Surf
                    • 2019 Chaparral 21 H2O Surf
                    • 2019 Chaparral 21 H2O Surf
                    • 2019 Chaparral 21 H2O Surf
                    • 2022 Chaparral 21 Surf

                      $57,800

                      $431/mo*

                      Fort Worth, TX | North Texas Marine- Fort Worth

                      • 2022 Chaparral 21 Surf
                      • 2022 Chaparral 21 Surf
                      • 2022 Chaparral 21 Surf
                      • 2022 Chaparral 21 Surf
                      • 2021 Chaparral 30 Surf

                        $129,900

                        $968/mo*

                        Saint Clair Shores, MI 48080 | Lakeside Formula

                        • 2021 Chaparral 30 Surf
                        • 2021 Chaparral 30 Surf
                        • 2021 Chaparral 30 Surf
                        • 2021 Chaparral 30 Surf

                        2020 Chaparral 25 Surf

                        $99,900

                        $744/mo*

                        Little Rock, AR 72209 | Export Marine Inc.

                        • 2020 Chaparral 25 Surf
                        • 2020 Chaparral 25 Surf
                        • 2020 Chaparral 25 Surf
                        • 2020 Chaparral 25 Surf
                        • 2022 Chaparral 21 Surf

                          $65,500

                          $488/mo*

                          Traverse City, MI 49685 | Action Water Sports -- Traverse City

                          • 2022 Chaparral 21 Surf
                          • 2022 Chaparral 21 Surf
                          • 2022 Chaparral 21 Surf
                          • 2022 Chaparral 21 Surf

                          2021 Chaparral 30 Surf

                          $159,000

                          $1,185/mo*

                          Lake Elsinore, CA 92530 | Pacific Freedom Marine

                          • 2021 Chaparral 30 Surf
                          • 2021 Chaparral 30 Surf
                          • 2021 Chaparral 30 Surf
                          • 2021 Chaparral 30 Surf

                          2022 Chaparral 23 Surf

                          $90,000

                          $670/mo*

                          Nashville, TN 37203 | Modern Marine

                          • 2022 Chaparral 23 Surf
                          • 2022 Chaparral 23 Surf
                          • 2022 Chaparral 23 Surf
                          • 2022 Chaparral 23 Surf

                          2023 Chaparral 21 Surf

                          $71,500

                          $533/mo*

                          Nashville, TN 37203 | Modern Marine

                          • 2023 Chaparral 21 Surf
                          • 2023 Chaparral 21 Surf
                          • 2023 Chaparral 21 Surf
                          • 2023 Chaparral 21 Surf
                          • 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
                            • 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
                              • 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

                                2023 Chaparral 23 Surf

                                $89,500

                                $667/mo*

                                Bracey, VA 23919 | Poplar Pointe Marine

                                • 2023 Chaparral 23 Surf
                                • 2023 Chaparral 23 Surf
                                • 2023 Chaparral 23 Surf
                                • 2023 Chaparral 23 Surf

                                2019 Chaparral 21 H2O Surf

                                $59,995

                                $447/mo*

                                Broadway, NC 27505 | NC Wake Boats

                                • 2019 Chaparral 21 H2O Surf
                                • 2019 Chaparral 21 H2O Surf
                                • 2019 Chaparral 21 H2O Surf
                                • 2019 Chaparral 21 H2O Surf
                                • 2021 Chaparral 26 Surf

                                  $129,995

                                  $968/mo*

                                  West Union, SC 29696 | All Florida Yacht Sales

                                  • 2021 Chaparral 26 Surf
                                  • 2021 Chaparral 26 Surf
                                  • 2021 Chaparral 26 Surf
                                  • 2021 Chaparral 26 Surf
                                  • 2021 Chaparral 26 Surf

                                    $99,900

                                    $744/mo*

                                    Lake Geneva, WI 53147 | Private Seller

                                    • 2021 Chaparral 26 Surf
                                    • 2021 Chaparral 26 Surf
                                    • 2021 Chaparral 26 Surf
                                    • 2021 Chaparral 26 Surf
                                      • 2023 Chaparral 30 Surf

                                        $189,900

                                        $1,415/mo*

                                        Ridgedale, MO 65739 | Private Seller

                                        • 2023 Chaparral 30 Surf
                                        • 2023 Chaparral 30 Surf
                                        • 2023 Chaparral 30 Surf
                                        • 2023 Chaparral 30 Surf
                                          • 2022 Chaparral 21 Surf

                                            $65,500

                                            $488/mo*

                                            Traverse City, MI 49685 | Action Water Sports -- Traverse City

                                            • 2022 Chaparral 21 Surf
                                            • 2022 Chaparral 21 Surf
                                            • 2022 Chaparral 21 Surf
                                            • 2022 Chaparral 21 Surf
                                            Dealer Logo
                                            • 2021 Chaparral 30 Surf

                                              $159,000

                                              $1,185/mo*

                                              Charleston, SC 29492 | Longshore Boats

                                              • 2021 Chaparral 30 Surf
                                              • 2021 Chaparral 30 Surf
                                              • 2021 Chaparral 30 Surf
                                              • 2021 Chaparral 30 Surf
                                              Dealer Logo
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