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Cobra Python, Bennington Sloop boats for sale

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116 more Models...
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    186 boats
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    • Price: Low to High

      2026 Bennington 24 MFB

      Request a Price

      Port St Joe, FL 32456 | Grander Marine

      • 2026 Bennington 24 MFB
      • 2026 Bennington 24 MFB
      • 2026 Bennington 24 MFB
      • 2026 Bennington 24 MFB
      Dealer Logo

      2011 Bennington 2554GCW

      $26,995

      $235/mo*

      Austin, TX 78735 | South Austin Marine Corp

      • 2011 Bennington 2554GCW
      • 2011 Bennington 2554GCW
      • 2011 Bennington 2554GCW
      • 2011 Bennington 2554GCW
      Dealer Logo

      2025 Bennington 23RSBA

      $156,516

      $1,166/mo*

      Greenville, SC 29605 | MarineMax Greenville

      • 2025 Bennington 23RSBA
      • 2025 Bennington 23RSBA
      • 2025 Bennington 23RSBA
      • 2025 Bennington 23RSBA
      Dealer Logo

      2026 Bennington 20 SL

      $38,997

      $339/mo*

      Fleming Island, FL 32003 | Bluewater Marine Fleming Island

      • 2026 Bennington 20 SL
      • 2026 Bennington 20 SL
      • 2026 Bennington 20 SL
      • 2026 Bennington 20 SL
      • 2018 Bennington 25 R

        $89,995

        $670/mo*

        Austin, TX 78735 | South Austin Marine - Lakeside

        • 2018 Bennington 25 R
        • 2018 Bennington 25 R
        • 2018 Bennington 25 R
        • 2018 Bennington 25 R
        • 2026 Bennington 22 S FISH AND CRUISE

          $64,915

          $484/mo*

          Port Orange, FL 32127 | Blue Water Marine Port Orange

          • 2026 Bennington 22 S FISH AND CRUISE
          • 2026 Bennington 22 S FISH AND CRUISE
          • 2026 Bennington 22 S FISH AND CRUISE
          • 2026 Bennington 22 S FISH AND CRUISE

          2015 Bennington 2575 QCW I/O Sport Arch

          $69,995

          $521/mo*

          Austin, TX 78734 | South Austin Marine - Lakeside

          • 2015 Bennington 2575 QCW I/O Sport Arch
          • 2015 Bennington 2575 QCW I/O Sport Arch
          • 2015 Bennington 2575 QCW I/O Sport Arch
          • 2015 Bennington 2575 QCW I/O Sport Arch
          • 2008 Bennington 2575RCW I/O

            $44,900

            $391/mo*

            Lake Havasu City, AZ 86403 | Sun Country Marine Group, Lake Havasu City, AZ

            • 2008 Bennington 2575RCW I/O
            • 2008 Bennington 2575RCW I/O
            • 2008 Bennington 2575RCW I/O
            • 2008 Bennington 2575RCW I/O
            • 2024 Bennington 20 SFNP

              $45,000

              $392/mo*

              US | TAILWALKER MARINE

              • 2024 Bennington 20 SFNP
              • 2024 Bennington 20 SFNP
              • 2024 Bennington 20 SFNP
              • 2024 Bennington 20 SFNP

              2021 Bennington 25 RTSB

              $79,900

              $595/mo*

              Orange Beach, AL 36561 | Grander Marine

              • 2021 Bennington 25 RTSB
              • 2021 Bennington 25 RTSB
              • 2021 Bennington 25 RTSB
              • 2021 Bennington 25 RTSB
              • 2025 Bennington 24LSR

                $74,500

                $555/mo*

                US | TAILWALKER MARINE

                • 2025 Bennington 24LSR
                • 2025 Bennington 24LSR
                • 2025 Bennington 24LSR
                • 2025 Bennington 24LSR

                2024 Bennington 30 QSBWAX2 ESP

                Request a Price

                Lewisville, TX 75067 | Phil Dill Boats

                2024 Bennington 30 QSBWAX2 ESP

                2024 Bennington 24 LXSFB SPS

                Request a Price

                Ft. Myers, FL 33908 | Marina Mikes

                2024 Bennington 24 LXSFB SPS

                2024 Bennington 30 QSBWAX2 ESP

                Request a Price

                Ft. Myers, FL 33908 | Marina Mikes

                2024 Bennington 30 QSBWAX2 ESP

                2024 Bennington 23 QXFBA ESP

                Request a Price

                Ft. Myers, FL 33908 | Marina Mikes

                2024 Bennington 23 QXFBA ESP
                • 2026 Bennington 22 SS

                  $64,972

                  $484/mo*

                  Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                  • 2026 Bennington 22 SS
                  • 2026 Bennington 22 SS
                  • 2026 Bennington 22 SS
                  • 2026 Bennington 22 SS
                  • 2019 Bennington Q 25 QCW

                    $79,995

                    $596/mo*

                    Austin, TX 78735 | South Austin Marine Corp

                    • 2019 Bennington Q 25 QCW
                    • 2019 Bennington Q 25 QCW
                    • 2019 Bennington Q 25 QCW
                    • 2019 Bennington Q 25 QCW

                    2024 Bennington 28 QXFBAX1 ESP

                    Request a Price

                    Ft. Myers, FL 33908 | Marina Mikes

                    2024 Bennington 28 QXFBAX1 ESP
                    • 2026 Bennington 18 S FISH AND CRUISE

                      $42,793

                      $373/mo*

                      Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                      • 2026 Bennington 18 S FISH AND CRUISE
                      • 2026 Bennington 18 S FISH AND CRUISE
                      • 2026 Bennington 18 S FISH AND CRUISE
                      • 2026 Bennington 18 S FISH AND CRUISE

                      2026 Bennington 26 MFB

                      Request a Price

                      Lake Havasu City, AZ 86403 | Sun Country Marine Group, Lake Havasu City, AZ

                      • 2026 Bennington 26 MFB
                      • 2026 Bennington 26 MFB
                      • 2026 Bennington 26 MFB
                      • 2026 Bennington 26 MFB

                      2024 Bennington 27 QXSBWAX2 ESP

                      Request a Price

                      Ft. Myers, FL 33908 | Marina Mikes

                      2024 Bennington 27 QXSBWAX2 ESP

                      2026 Bennington 22 MFB

                      Request a Price

                      Orange Beach, AL 36561 | Grander Marine

                      • 2026 Bennington 22 MFB
                      • 2026 Bennington 22 MFB
                      • 2026 Bennington 22 MFB
                      • 2026 Bennington 22 MFB

                      2026 Bennington 21 S SWINGBACK

                      $68,479

                      $510/mo*

                      Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                      • 2026 Bennington 21 S SWINGBACK
                      • 2026 Bennington 21 S SWINGBACK
                      • 2026 Bennington 21 S SWINGBACK
                      • 2026 Bennington 21 S SWINGBACK
                      • 2011 Bennington 2554GCW

                        $26,995

                        $235/mo*

                        Austin, TX 78735 | South Austin Marine Corp

                        • 2011 Bennington 2554GCW
                        • 2011 Bennington 2554GCW
                        • 2011 Bennington 2554GCW
                        • 2011 Bennington 2554GCW
                        • 2026 Bennington 16 S CRUISE JUMP SEAT

                          $34,980

                          $305/mo*

                          Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                          • 2026 Bennington 16 S CRUISE JUMP SEAT
                          • 2026 Bennington 16 S CRUISE JUMP SEAT
                          • 2026 Bennington 16 S CRUISE JUMP SEAT
                          • 2026 Bennington 16 S CRUISE JUMP SEAT
                          • 2019 Bennington 218SLDN

                            $25,000

                            $218/mo*

                            Austin, TX 78735 | South Austin Marine Corp

                            • 2019 Bennington 218SLDN
                            • 2019 Bennington 218SLDN
                            • 2019 Bennington 218SLDN
                            • 2019 Bennington 218SLDN

                            2026 Bennington 22 SSR

                            $59,930

                            $446/mo*

                            Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                            • 2026 Bennington 22 SSR
                            • 2026 Bennington 22 SSR
                            • 2026 Bennington 22 SSR
                            • 2026 Bennington 22 SSR

                            2026 Bennington 20SXSNP REAR FISH

                            $47,995

                            $418/mo*

                            Waco, TX 76710 | Yowells Boat Yard Inc.

                            • 2026 Bennington 20SXSNP REAR FISH
                            • 2026 Bennington 20SXSNP REAR FISH
                            • 2026 Bennington 20SXSNP REAR FISH
                            • 2026 Bennington 20SXSNP REAR FISH
                            • 2026 Bennington 21 S FISH AND CRUISE

                              $56,802

                              $423/mo*

                              Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                              • 2026 Bennington 21 S FISH AND CRUISE
                              • 2026 Bennington 21 S FISH AND CRUISE
                              • 2026 Bennington 21 S FISH AND CRUISE
                              • 2026 Bennington 21 S FISH AND CRUISE

                              2026 Bennington SX SWING BACK

                              $69,995

                              ↓ Price Drop

                              $521/mo*

                              Waco, TX 76710 | Yowells Boat Yard Inc.

                              • 2026 Bennington SX SWING BACK
                              • 2026 Bennington SX SWING BACK
                              • 2026 Bennington SX SWING BACK
                              • 2026 Bennington SX SWING BACK

                              2026 Bennington 22 MSB

                              Request a Price

                              Lake Havasu City, AZ 86403 | Sun Country Marine Group, Lake Havasu City, AZ

                              • 2026 Bennington 22 MSB
                              • 2026 Bennington 22 MSB
                              • 2026 Bennington 22 MSB
                              • 2026 Bennington 22 MSB

                              2025 Bennington 22 ML

                              $84,658

                              $631/mo*

                              Port Orange, FL 32129 | Blue Water Marine Port Orange

                              • 2025 Bennington 22 ML
                              • 2025 Bennington 22 ML
                              • 2025 Bennington 22 ML
                              • 2025 Bennington 22 ML

                              2026 Bennington 26 MSB

                              Request a Price

                              Lake Havasu City, AZ 86403 | Sun Country Marine Group, Lake Havasu City, AZ

                              • 2026 Bennington 26 MSB
                              • 2026 Bennington 26 MSB
                              • 2026 Bennington 26 MSB
                              • 2026 Bennington 26 MSB

                              2021 Bennington 25RX

                              $119,226

                              ↓ Price Drop

                              $888/mo*

                              Greenville, SC 29605 | MarineMax Greenville

                              • 2021 Bennington 25RX
                              • 2021 Bennington 25RX
                              • 2021 Bennington 25RX
                              • 2021 Bennington 25RX
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