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New Cobra Python, Bennington Sloop boats for sale

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149 more Makes...
Bennington Models
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14 more Models...
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    30 boats
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      2026 Bennington 22 SF

      Request a Price

      Indianapolis, IN 46204 | Reeder Trausch Marine Indianapolis

      • 2026 Bennington 22 SF
      • 2026 Bennington 22 SF
      • 2026 Bennington 22 SF
      • 2026 Bennington 22 SF
      Dealer Logo

      2025 Bennington 22SSRSE

      $73,419

      $547/mo*

      Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

      • 2025 Bennington 22SSRSE
      • 2025 Bennington 22SSRSE
      • 2025 Bennington 22SSRSE
      • 2025 Bennington 22SSRSE
      Dealer Logo

      2025 Bennington 22MFBSE

      $92,782

      $691/mo*

      Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

      • 2025 Bennington 22MFBSE
      • 2025 Bennington 22MFBSE
      • 2025 Bennington 22MFBSE
      • 2025 Bennington 22MFBSE
      Dealer Logo
      • 2025 Bennington 21 SF Family / 4 Fishing seat (In Stock)

        $36,999

        $322/mo*

        Spring Grove, PA 17362 | F & S Yamaha & Marine

        • 2025 Bennington 21 SF Family / 4 Fishing seat (In Stock)
        • 2025 Bennington 21 SF Family / 4 Fishing seat (In Stock)
        • 2025 Bennington 21 SF Family / 4 Fishing seat (In Stock)
        • 2025 Bennington 21 SF Family / 4 Fishing seat (In Stock)

        2026 Bennington 20 SS Family / Fishing

        $44,713

        $389/mo*

        Spring Grove, PA 17362 | F & S Yamaha & Marine

        • 2026 Bennington 20 SS Family / Fishing
        • 2026 Bennington 20 SS Family / Fishing
        • 2026 Bennington 20 SS Family / Fishing
        • 2026 Bennington 20 SS Family / Fishing
        • 2025 Bennington 22SSRSE

          $54,218

          $404/mo*

          Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

          • 2025 Bennington 22SSRSE
          • 2025 Bennington 22SSRSE
          • 2025 Bennington 22SSRSE
          • 2025 Bennington 22SSRSE
          • 2025 Bennington 22SSRSE

            $63,911

            $476/mo*

            Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

            • 2025 Bennington 22SSRSE
            • 2025 Bennington 22SSRSE
            • 2025 Bennington 22SSRSE
            • 2025 Bennington 22SSRSE

            2026 Bennington 168 SF Electric

            $27,999

            $244/mo*

            Hennepin, IL 61327 | Hennepin Marine Inc.

            • 2026 Bennington 168 SF Electric
            • 2026 Bennington 168 SF Electric
            • 2026 Bennington 168 SF Electric
            • 2026 Bennington 168 SF Electric
            • 2023 Bennington 22SXSBSP

              $63,952

              $476/mo*

              Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

              • 2023 Bennington 22SXSBSP
              • 2023 Bennington 22SXSBSP
              • 2023 Bennington 22SXSBSP
              • 2023 Bennington 22SXSBSP
              • 2025 Bennington 22MSBSE

                $92,056

                $686/mo*

                Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                • 2025 Bennington 22MSBSE
                • 2025 Bennington 22MSBSE
                • 2025 Bennington 22MSBSE
                • 2025 Bennington 22MSBSE
                • 2025 Bennington 22SSBSE

                  $74,381

                  $554/mo*

                  Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                  • 2025 Bennington 22SSBSE
                  • 2025 Bennington 22SSBSE
                  • 2025 Bennington 22SSBSE
                  • 2025 Bennington 22SSBSE
                  • 2025 Bennington 22SSRSE

                    $64,146

                    $478/mo*

                    Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                    • 2025 Bennington 22SSRSE
                    • 2025 Bennington 22SSRSE
                    • 2025 Bennington 22SSRSE
                    • 2025 Bennington 22SSRSE
                    • 2025 Bennington 25SSBSE

                      $91,866

                      $684/mo*

                      Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                      • 2025 Bennington 25SSBSE
                      • 2025 Bennington 25SSBSE
                      • 2025 Bennington 25SSBSE
                      • 2025 Bennington 25SSBSE
                      • 2025 Bennington 22MFBSE

                        $92,782

                        $691/mo*

                        Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                        • 2025 Bennington 22MFBSE
                        • 2025 Bennington 22MFBSE
                        • 2025 Bennington 22MFBSE
                        • 2025 Bennington 22MFBSE
                        • 2025 Bennington 25SSRSE

                          $89,929

                          $670/mo*

                          Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                          • 2025 Bennington 25SSRSE
                          • 2025 Bennington 25SSRSE
                          • 2025 Bennington 25SSRSE
                          • 2025 Bennington 25SSRSE
                          • 2025 Bennington 22SSRSE

                            $64,146

                            $478/mo*

                            Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                            • 2025 Bennington 22SSRSE
                            • 2025 Bennington 22SSRSE
                            • 2025 Bennington 22SSRSE
                            • 2025 Bennington 22SSRSE

                            2023 Bennington 23LFBCSP

                            $55,000

                            ↓ Price Drop

                            $410/mo*

                            Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                            • 2023 Bennington 23LFBCSP
                            • 2023 Bennington 23LFBCSP
                            • 2023 Bennington 23LFBCSP
                            • 2023 Bennington 23LFBCSP
                            • 2025 Bennington 22SSBSE

                              $76,072

                              $567/mo*

                              Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                              • 2025 Bennington 22SSBSE
                              • 2025 Bennington 22SSBSE
                              • 2025 Bennington 22SSBSE
                              • 2025 Bennington 22SSBSE
                              • 2025 Bennington 22SSRSE

                                $73,419

                                $547/mo*

                                Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                                • 2025 Bennington 22SSRSE
                                • 2025 Bennington 22SSRSE
                                • 2025 Bennington 22SSRSE
                                • 2025 Bennington 22SSRSE

                                2026 Bennington 22 SF

                                Request a Price

                                Indianapolis, IN 46204 | Reeder Trausch Marine

                                • 2026 Bennington 22 SF
                                • 2026 Bennington 22 SF
                                • 2026 Bennington 22 SF
                                • 2026 Bennington 22 SF
                                • 2025 Bennington 25RSXBWASE

                                  $189,838

                                  $1,414/mo*

                                  Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                                  • 2025 Bennington 25RSXBWASE
                                  • 2025 Bennington 25RSXBWASE
                                  • 2025 Bennington 25RSXBWASE
                                  • 2025 Bennington 25RSXBWASE
                                  • 2026 Bennington 20 S-One Fish

                                    Request a Price

                                    Fairfield, OH 45014 | Hern Marine

                                    • 2026 Bennington 20 S-One Fish
                                    • 2026 Bennington 20 S-One Fish
                                    • 2026 Bennington 20 S-One Fish

                                    2024 Bennington 27QFBWAT2SR

                                    $178,000

                                    ↓ Price Drop

                                    $1,326/mo*

                                    Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                                    • 2024 Bennington 27QFBWAT2SR
                                    • 2024 Bennington 27QFBWAT2SR
                                    • 2024 Bennington 27QFBWAT2SR
                                    • 2024 Bennington 27QFBWAT2SR
                                    • 2025 Bennington 21SXSAPG

                                      $58,000

                                      $432/mo*

                                      INVERNESS, FL 34453 | Apopka Marine

                                      • 2025 Bennington 21SXSAPG
                                      • 2025 Bennington 21SXSAPG
                                      • 2025 Bennington 21SXSAPG
                                      • 2025 Bennington 21SXSAPG
                                      • 2026 Bennington 21SFC

                                        $61,500

                                        $458/mo*

                                        INVERNESS, FL 34453 | Apopka Marine

                                        • 2026 Bennington 21SFC
                                        • 2026 Bennington 21SFC
                                        • 2026 Bennington 21SFC
                                        • 2026 Bennington 21SFC
                                        • 2026 Bennington 20SXS

                                          $49,995

                                          $435/mo*

                                          INVERNESS, FL 34453 | Apopka Marine

                                          • 2026 Bennington 20SXS
                                          • 2026 Bennington 20SXS
                                          • 2026 Bennington 20SXS
                                          • 2026 Bennington 20SXS
                                          • 2024 Bennington 20SVF

                                            $39,995

                                            $348/mo*

                                            INVERNESS, FL 34453 | Apopka Marine

                                            • 2024 Bennington 20SVF
                                            • 2024 Bennington 20SVF
                                            • 2024 Bennington 20SVF
                                            • 2024 Bennington 20SVF
                                            • 2026 Bennington 20SS

                                              $41,900

                                              $365/mo*

                                              INVERNESS, FL 34453 | Apopka Marine

                                              • 2026 Bennington 20SS
                                              • 2026 Bennington 20SS
                                              • 2026 Bennington 20SS
                                              • 2026 Bennington 20SS
                                              • 2025 Bennington 22SSB

                                                $52,995

                                                $395/mo*

                                                INVERNESS, FL 34453 | Apopka Marine

                                                • 2025 Bennington 22SSB
                                                • 2025 Bennington 22SSB
                                                • 2025 Bennington 22SSB
                                                • 2025 Bennington 22SSB
                                                • 2026 Bennington 188SS

                                                  $34,800

                                                  $303/mo*

                                                  INVERNESS, FL 34453 | Apopka Marine

                                                  • 2026 Bennington 188SS
                                                  • 2026 Bennington 188SS
                                                  • 2026 Bennington 188SS
                                                  • 2026 Bennington 188SS
                                                  • 2025 Bennington 21SF

                                                    $54,700

                                                    $408/mo*

                                                    INVERNESS, FL 34453 | Apopka Marine

                                                    • 2025 Bennington 21SF
                                                    • 2025 Bennington 21SF
                                                    • 2025 Bennington 21SF
                                                    • 2025 Bennington 21SF
                                                    • 2025 Bennington 168SF

                                                      $28,395

                                                      $247/mo*

                                                      INVERNESS, FL 34453 | Apopka Marine

                                                      • 2025 Bennington 168SF
                                                      • 2025 Bennington 168SF
                                                      • 2025 Bennington 168SF
                                                      • 2025 Bennington 168SF
                                                      • 2025 Bennington 21SF

                                                        $54,700

                                                        $408/mo*

                                                        INVERNESS, FL 34453 | Apopka Marine

                                                        • 2025 Bennington 21SF
                                                        • 2025 Bennington 21SF
                                                        • 2025 Bennington 21SF
                                                        • 2025 Bennington 21SF
                                                        • 2025 Bennington 22SSBSE

                                                          $74,381

                                                          $554/mo*

                                                          Gulfport, MS 39501 | Ocean Marine Group - Gulfport, MS

                                                          • 2025 Bennington 22SSBSE
                                                          • 2025 Bennington 22SSBSE
                                                          • 2025 Bennington 22SSBSE
                                                          • 2025 Bennington 22SSBSE
                                                          Dealer Logo
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