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  • Bennington

New Bennington Sloop boats for sale

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154 more Makes...
Bennington Models
  • 21 SSB
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    46 boats
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    • Price: High to Low
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      2026 Bennington 20SXSNP REAR FISH

      $49,995

      $435/mo*

      Waco, TX 76710 | Yowells Boat Yard Inc.

      2026 Bennington 20SXSNP REAR FISH
      • 2026 Bennington 20 SSR

        $39,791

        $346/mo*

        Fleming Island, FL 32003 | Bluewater Marine Fleming Island

        2026 Bennington 20 SSR

        2026 Bennington 20SSRCX STERN RADIUS

        $49,995

        $435/mo*

        Waco, TX 76710 | Yowells Boat Yard Inc.

        2026 Bennington 20SSRCX STERN RADIUS
        • 2026 Bennington 22 SSR

          $59,930

          $446/mo*

          Port Orange, FL 32127 | Blue Water Marine Port Orange

          2026 Bennington 22 SSR

          2025 Bennington 20 SSRCX STERN RADIOS

          $45,995

          $400/mo*

          Waco, TX 76710 | Yowells Boat Yard Inc.

          2025 Bennington 20 SSRCX STERN RADIOS
          • 2026 Bennington 22 S CRUISE JUMP SEAT

            $63,976

            $477/mo*

            Port Orange, FL 32127 | Blue Water Marine Port Orange

            2026 Bennington 22 S CRUISE JUMP SEAT

            2026 Bennington 21 SSB

            $65,995

            $492/mo*

            Campbell, CA 95008 | Sun Country Marine Group

            2026 Bennington 21 SSB

            2025 Bennington 22 ML

            $73,900

            ↓ Price Drop

            $551/mo*

            Port Orange, FL 32127 | Blue Water Marine Port Orange

            2025 Bennington 22 ML

            2026 Bennington 20SXSNP REAR FISH

            $49,995

            $435/mo*

            Waco, TX 76710 | Yowells Boat Yard Inc.

            2026 Bennington 20SXSNP REAR FISH
            • 2026 Bennington 22 SSB

              $62,938

              $469/mo*

              Port Orange, FL 32127 | Blue Water Marine Port Orange

              2026 Bennington 22 SSB

              2026 Bennington 26 MCSB

              $134,885

              $1,005/mo*

              Lake Havasu City, AZ 86403 | Sun Country Marine Group

              2026 Bennington 26 MCSB

              2026 Bennington SX SWING BACK

              $74,495

              $555/mo*

              Waco, TX 76710 | Yowells Boat Yard Inc.

              2026 Bennington SX SWING BACK

              2026 Bennington 22 MSB

              $92,970

              $693/mo*

              Lake Havasu City, AZ 86403 | Sun Country Marine Group

              2026 Bennington 22 MSB

              2023 Ranger Reata 220C

              $46,995

              $409/mo*

              Fredericktown, OH 43019 | Knox Marine - Ltd

              2023 Ranger Reata 220C

              2026 Sun Tracker SportFish 20 DLX

              $42,755

              $372/mo*

              Columbus, OH 43224 | Sizzle Marine

              2026 Sun Tracker SportFish 20 DLX

              2024 Godfrey SWEETWATER 2286 SFL

              $57,995

              $432/mo*

              Columbus, OH 43224 | Sizzle Marine

              2024 Godfrey SWEETWATER 2286 SFL

              2026 Bennington 22SX Stern Radius

              $65,495

              $488/mo*

              Waco, TX 76710 | Yowells Boat Yard Inc.

              2026 Bennington 22SX Stern Radius

              2026 Bennington 22 MSB

              $90,516

              $674/mo*

              Lake Havasu City, AZ 86403 | Sun Country Marine Group

              2026 Bennington 22 MSB

              2026 Bennington 22 SSB

              $52,999

              $395/mo*

              Orange Beach, AL 36561 | Grander Marine

              2026 Bennington 22 SSB

              2026 Bennington 26 MSB

              $128,083

              $954/mo*

              Lake Havasu City, AZ 86403 | Sun Country Marine Group

              2026 Bennington 26 MSB

              2026 Bennington 26 MFB

              $126,748

              $944/mo*

              Lake Havasu City, AZ 86403 | Sun Country Marine Group

              2026 Bennington 26 MFB

              2026 Bennington 21 SSB

              $64,816

              $483/mo*

              Lake Havasu City, AZ 86403 | Sun Country Marine Group

              2026 Bennington 21 SSB
              • 2026 Bennington 20 SL

                $38,957

                $339/mo*

                Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                2026 Bennington 20 SL
                • 2026 Bennington 20 SL

                  $38,997

                  $339/mo*

                  Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                  2026 Bennington 20 SL

                  2025 Bennington 24 MFB

                  $115,000

                  ↓ Price Drop

                  $857/mo*

                  Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                  2025 Bennington 24 MFB
                  • 2026 Bennington 22 SS

                    $64,972

                    $484/mo*

                    Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                    2026 Bennington 22 SS

                    2026 Bennington 24 MSL

                    $115,994

                    $864/mo*

                    Lake Havasu City, AZ 86403 | Sun Country Marine Group

                    2026 Bennington 24 MSL

                    2025 Bennington 20 SSR

                    $37,786

                    ↓ Price Drop

                    $329/mo*

                    Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                    2025 Bennington 20 SSR

                    2026 Bennington 21 SSB

                    $64,816

                    $483/mo*

                    Lake Havasu City, AZ 86403 | Sun Country Marine Group

                    2026 Bennington 21 SSB

                    2026 Bennington 188 SLE

                    Request a Price

                    Lake Havasu City, AZ 86403 | Sun Country Marine Group

                    2026 Bennington 188 SLE

                    2026 Bennington 24 MSL

                    $115,994

                    $864/mo*

                    Costa Mesa, CA 92614 | Sun Country Marine Group

                    2026 Bennington 24 MSL
                    • 2026 Bennington 22 SSR

                      $59,930

                      $446/mo*

                      Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                      2026 Bennington 22 SSR
                      • 2026 Bennington 22 SSB

                        $62,937

                        $469/mo*

                        Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                        2026 Bennington 22 SSB
                        • 2025 Bennington 22 MFB

                          $79,893

                          $595/mo*

                          Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                          2025 Bennington 22 MFB
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