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Cobra Python, Bennington 20 Sloop boats for sale

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    159 boats
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      2026 Bennington S Quad Bench 20 SSR Tritoon

      $44,095

      $384/mo*

      Red Wing, MN 55066 | River Valley Marine – Red Wing

      • 2026 Bennington S Quad Bench 20 SSR Tritoon
      • 2026 Bennington S Quad Bench 20 SSR Tritoon
      Dealer Logo

      2026 Bennington S-One L-Bench 20 SL Pontoon

      $32,445

      $282/mo*

      Red Wing, MN 55066 | River Valley Marine – Red Wing

      • 2026 Bennington S-One L-Bench 20 SL Pontoon
      • 2026 Bennington S-One L-Bench 20 SL Pontoon
      Dealer Logo

      2026 Bennington S-One Fishing 20 SF Pontoon

      $34,995

      $305/mo*

      Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

      • 2026 Bennington S-One Fishing 20 SF Pontoon
      • 2026 Bennington S-One Fishing 20 SF Pontoon
      Dealer Logo
      • 2024 Bennington S Fishing 20 SF Pontoon

        $39,114

        $341/mo*

        Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

        • 2024 Bennington S Fishing 20 SF Pontoon
        • 2024 Bennington S Fishing 20 SF Pontoon
        • 2024 Bennington S Fishing 20 SF Pontoon
        • 2024 Bennington S Fishing 20 SF Pontoon
        • 2024 Bennington S Fishing 20 SF Pontoon

          $40,364

          $351/mo*

          Rochester, MN 55901 | River Valley Marine – Rochester

          • 2024 Bennington S Fishing 20 SF Pontoon
          • 2024 Bennington S Fishing 20 SF Pontoon
          • 2024 Bennington S Fishing 20 SF Pontoon
          • 2024 Bennington S Fishing 20 SF Pontoon
          • 2024 Bennington S Fishing 20 SF Pontoon

            $36,359

            $317/mo*

            Rochester, MN 55901 | River Valley Marine – Rochester

            • 2024 Bennington S Fishing 20 SF Pontoon
            • 2024 Bennington S Fishing 20 SF Pontoon
            • 2024 Bennington S Fishing 20 SF Pontoon
            • 2024 Bennington S Fishing 20 SF Pontoon
            • 2024 Bennington SV Fishing 20 SVF Pontoon

              $31,561

              $275/mo*

              Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

              • 2024 Bennington SV Fishing 20 SVF Pontoon
              • 2024 Bennington SV Fishing 20 SVF Pontoon
              • 2024 Bennington SV Fishing 20 SVF Pontoon
              • 2024 Bennington SV Fishing 20 SVF Pontoon
              • 2024 Bennington 20 SSB - Swingback - Pontoon

                $39,999

                $348/mo*

                Red Wing, MN 55066 | River Valley Marine – Red Wing

                • 2024 Bennington 20 SSB - Swingback - Pontoon
                • 2024 Bennington 20 SSB - Swingback - Pontoon
                • 2024 Bennington 20 SSB - Swingback - Pontoon
                • 2024 Bennington 20 SSB - Swingback - Pontoon
                • 2024 Bennington S Fishing 20 SF Pontoon

                  $40,364

                  $351/mo*

                  Red Wing, MN 55066 | River Valley Marine – Red Wing

                  • 2024 Bennington S Fishing 20 SF Pontoon
                  • 2024 Bennington S Fishing 20 SF Pontoon
                  • 2024 Bennington S Fishing 20 SF Pontoon
                  • 2024 Bennington S Fishing 20 SF Pontoon
                  • 2024 Bennington 20 SSB - Swingback - Pontoon

                    $39,999

                    $348/mo*

                    Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

                    • 2024 Bennington 20 SSB - Swingback - Pontoon
                    • 2024 Bennington 20 SSB - Swingback - Pontoon
                    • 2024 Bennington 20 SSB - Swingback - Pontoon
                    • 2024 Bennington 20 SSB - Swingback - Pontoon
                    • 2024 Bennington S Fishing 20 SF Pontoon

                      $36,359

                      $317/mo*

                      Red Wing, MN 55066 | River Valley Marine – Red Wing

                      • 2024 Bennington S Fishing 20 SF Pontoon
                      • 2024 Bennington S Fishing 20 SF Pontoon
                      • 2024 Bennington S Fishing 20 SF Pontoon
                      • 2024 Bennington S Fishing 20 SF Pontoon
                      • 2024 Bennington S Fishing 20 SF Pontoon

                        $39,114

                        $341/mo*

                        Rochester, MN 55901 | River Valley Marine – Rochester

                        • 2024 Bennington S Fishing 20 SF Pontoon
                        • 2024 Bennington S Fishing 20 SF Pontoon
                        • 2024 Bennington S Fishing 20 SF Pontoon
                        • 2024 Bennington S Fishing 20 SF Pontoon
                        • 2024 Bennington S Fishing 20 SF Pontoon

                          $40,364

                          $351/mo*

                          Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

                          • 2024 Bennington S Fishing 20 SF Pontoon
                          • 2024 Bennington S Fishing 20 SF Pontoon
                          • 2024 Bennington S Fishing 20 SF Pontoon
                          • 2024 Bennington S Fishing 20 SF Pontoon
                          • 2024 Bennington 20 SSB - Swingback - Pontoon

                            $39,999

                            $348/mo*

                            Rochester, MN 55901 | River Valley Marine – Rochester

                            • 2024 Bennington 20 SSB - Swingback - Pontoon
                            • 2024 Bennington 20 SSB - Swingback - Pontoon
                            • 2024 Bennington 20 SSB - Swingback - Pontoon
                            • 2024 Bennington 20 SSB - Swingback - Pontoon

                            2019 Bennington 20 ssxp

                            $30,599

                            $266/mo*

                            Mary Esther, US 32569 | Sunrise Marine - Destin

                            • 2019 Bennington 20 ssxp
                            • 2019 Bennington 20 ssxp
                            • 2019 Bennington 20 ssxp
                            • 2019 Bennington 20 ssxp
                            • 2024 Bennington S Fishing 20 SF Pontoon

                              $36,359

                              $317/mo*

                              Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

                              • 2024 Bennington S Fishing 20 SF Pontoon
                              • 2024 Bennington S Fishing 20 SF Pontoon
                              • 2024 Bennington S Fishing 20 SF Pontoon
                              • 2024 Bennington S Fishing 20 SF Pontoon

                              2020 Bennington 20 SSX

                              $24,970

                              ↓ Price Drop

                              Lake Wales, FL 33859 | Ridgeline Boating Center

                              • 2020 Bennington 20 SSX
                              • 2020 Bennington 20 SSX
                              • 2020 Bennington 20 SSX
                              • 2020 Bennington 20 SSX

                              2009 Bennington Cruise 20

                              $13,999

                              Sevierville, TN 37862 | Bass Pro Boating Center | Sevierville, TN

                              • 2009 Bennington Cruise 20
                              • 2009 Bennington Cruise 20
                              • 2009 Bennington Cruise 20
                              • 2009 Bennington Cruise 20
                              • 2026 Bennington 20 SVL

                                Request a Price

                                Port Charlotte, FL 33953 | Ingman Marine

                                • 2026 Bennington 20 SVL
                                • 2026 Bennington 20 SVL
                                • 2026 Bennington 20 SVL
                                • 2026 Bennington 20 SVL
                                • 2023 Bennington 20 SXL

                                  $44,999

                                  $392/mo*

                                  Littleton, NC 27850 | Rock Outdoors - High Rock Lake

                                  • 2023 Bennington 20 SXL
                                  • 2023 Bennington 20 SXL
                                  • 2023 Bennington 20 SXL
                                  • 2023 Bennington 20 SXL
                                  • 2023 Bennington 20 SXL

                                    $44,999

                                    $392/mo*

                                    Lexington, NC | Rock Outdoors - High Rock Lake

                                    • 2023 Bennington 20 SXL
                                    • 2023 Bennington 20 SXL
                                    • 2023 Bennington 20 SXL
                                    • 2023 Bennington 20 SXL
                                    • 2026 Bennington 20 SVL

                                      Request a Price

                                      Longboat Key, FL 34228 | Ingman Marine- Longboat Key

                                      • 2026 Bennington 20 SVL
                                      • 2026 Bennington 20 SVL
                                      • 2026 Bennington 20 SVL
                                      • 2026 Bennington 20 SVL
                                      • 2023 Bennington 20 SXL

                                        $44,999

                                        $392/mo*

                                        Littleton, NC 27850 | Rock Outdoors - High Rock Lake

                                        • 2023 Bennington 20 SXL
                                        • 2023 Bennington 20 SXL
                                        • 2023 Bennington 20 SXL
                                        • 2023 Bennington 20 SXL
                                        • 2026 Bennington 20 SVL

                                          Request a Price

                                          Sarasota, FL 34238 | Ingman Marine- Sarasota

                                          • 2026 Bennington 20 SVL
                                          • 2026 Bennington 20 SVL
                                          • 2026 Bennington 20 SVL
                                          • 2026 Bennington 20 SVL

                                          2024 Bennington 20 SL

                                          $69,999

                                          $521/mo*

                                          Winchester, TN 37398 | Tims Ford Powersports

                                          • 2024 Bennington 20 SL
                                          • 2024 Bennington 20 SL
                                          • 2024 Bennington 20 SL
                                          • 2024 Bennington 20 SL
                                          • 2023 Bennington 20 SXL

                                            $44,999

                                            $392/mo*

                                            Lexington, NC | Rock Outdoors - High Rock Lake

                                            • 2023 Bennington 20 SXL
                                            • 2023 Bennington 20 SXL
                                            • 2023 Bennington 20 SXL
                                            • 2023 Bennington 20 SXL

                                            2020 Bennington 20 SFV

                                            $22,500

                                            Mary Esther, US 32569 | Sunrise Marine - Destin

                                            • 2020 Bennington 20 SFV
                                            • 2020 Bennington 20 SFV
                                            • 2020 Bennington 20 SFV
                                            • 2020 Bennington 20 SFV
                                            • 2026 Bennington S-One Quad Bench 20 SSR Pontoon

                                              $33,945

                                              $296/mo*

                                              Red Wing, MN 55066 | River Valley Marine – Red Wing

                                              • 2026 Bennington S-One Quad Bench 20 SSR Pontoon
                                              • 2026 Bennington S-One Quad Bench 20 SSR Pontoon
                                              • 2026 Bennington S-One Quad Bench 20 SSR Pontoon
                                              • 2026 Bennington S-One Quad Bench 20 SSR Pontoon
                                              • 2026 Bennington S Quad Bench 20 SSR

                                                Request a Price

                                                New Lisbon, WI 53950 | V2 Boat Center Inc.

                                                • 2026 Bennington S Quad Bench 20 SSR
                                                • 2026 Bennington S Quad Bench 20 SSR
                                                • 2026 Bennington S Quad Bench 20 SSR
                                                • 2026 Bennington S Quad Bench 20 SSR
                                                • 2026 Bennington S Quad Bench 20 SSR Tritoon

                                                  $44,095

                                                  $384/mo*

                                                  Rochester, MN 55901 | River Valley Marine – Rochester

                                                  • 2026 Bennington S Quad Bench 20 SSR Tritoon
                                                  • 2026 Bennington S Quad Bench 20 SSR Tritoon
                                                  • 2026 Bennington S L-Bench 20 SL

                                                    Request a Price

                                                    New Lisbon, WI 53950 | V2 Boat Center Inc.

                                                    • 2026 Bennington S L-Bench 20 SL
                                                    • 2026 Bennington S L-Bench 20 SL
                                                    • 2026 Bennington S L-Bench 20 SL
                                                    • 2026 Bennington S L-Bench 20 SL
                                                    • 2026 Bennington S-One L Bench 20 SL Pontoon

                                                      $31,795

                                                      $277/mo*

                                                      Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

                                                      • 2026 Bennington S-One L Bench 20 SL Pontoon
                                                      • 2026 Bennington S-One L Bench 20 SL Pontoon
                                                      • 2026 Bennington S-One L Bench 20 SL Pontoon

                                                        $31,795

                                                        $277/mo*

                                                        Rochester, MN 55901 | River Valley Marine – Rochester

                                                        • 2026 Bennington S-One L Bench 20 SL Pontoon
                                                        • 2026 Bennington S-One L Bench 20 SL Pontoon
                                                        • 2026 Bennington S Quad Bench 20 SSR Pontoon

                                                          $33,295

                                                          $290/mo*

                                                          Rochester, MN 55901 | River Valley Marine – Rochester

                                                          • 2026 Bennington S Quad Bench 20 SSR Pontoon
                                                          • 2026 Bennington S Quad Bench 20 SSR Pontoon
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