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  • Bennington

Bennington Sloop boats for sale

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369 more Makes...
Bennington Models
  • 21 SSB
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53 more Models...
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    82 boats
    Sort: Recommended
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    • Price: High to Low
    • Price: Low to High
      • 2026 Bennington 22 SSR

        $59,930

        $446/mo*

        Port Orange, FL 32127 | Blue Water Marine Port Orange

        2026 Bennington 22 SSR
        • 2026 Bennington 22 SS

          $64,972

          $484/mo*

          Fleming Island, FL 32003 | Bluewater Marine Fleming Island

          2026 Bennington 22 SS
          • 2026 Bennington 20 SSR

            $39,791

            $346/mo*

            Fleming Island, FL 32003 | Bluewater Marine Fleming Island

            2026 Bennington 20 SSR
            • 2026 Bennington 20 SL

              $38,997

              $339/mo*

              Fleming Island, FL 32003 | Bluewater Marine Fleming Island

              2026 Bennington 20 SL
              • 2026 Bennington 20 SL

                $38,957

                $339/mo*

                Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                2026 Bennington 20 SL

                2026 Bennington 21 SSB

                $65,995

                $492/mo*

                Campbell, CA 95008 | Sun Country Marine Group

                2026 Bennington 21 SSB
                • 2020 Bennington QX 25 Sport

                  $179,995

                  $1,341/mo*

                  Austin, TX 78735 | South Austin Marine Corp

                  2020 Bennington QX 25 Sport

                  2003 Bennington 2275LX

                  $12,900

                  Irvine, CA 92614 | Sun Country Marine Group

                  2003 Bennington 2275LX
                  • 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

                    2011 Bennington 2554GCW

                    $26,995

                    ↓ Price Drop

                    $235/mo*

                    Austin, TX 78735 | South Austin Marine Corp

                    2011 Bennington 2554GCW

                    2025 Bennington 20 SSR

                    $37,786

                    ↓ Price Drop

                    $329/mo*

                    Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                    2025 Bennington 20 SSR

                    2019 Bennington 218SLDN

                    $32,995

                    ↓ Price Drop

                    $287/mo*

                    Austin, TX 78735 | South Austin Marine Corp

                    2019 Bennington 218SLDN

                    2025 Bennington 24 MFB

                    $115,000

                    ↓ Price Drop

                    $857/mo*

                    Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                    2025 Bennington 24 MFB

                    2025 Tahoe T16

                    $28,615

                    $249/mo*

                    Columbus, OH 43224 | Sizzle Marine

                    2025 Tahoe T16

                    2006 Bayliner 185 Bowrider

                    $11,995

                    Columbus, OH 43224 | Sizzle Marine

                    2006 Bayliner 185 Bowrider

                    2025 Tahoe 185 S

                    $43,200

                    $376/mo*

                    Columbus, OH 43224 | Sizzle Marine

                    2025 Tahoe 185 S
                    • 2026 Bennington 22 SSR

                      $59,930

                      $446/mo*

                      Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                      2026 Bennington 22 SSR

                      2021 Bennington 25 RTSB

                      $79,900

                      $595/mo*

                      Orange Beach, AL 36561 | Grander Marine

                      2021 Bennington 25 RTSB
                      • 2018 Bennington 25 R

                        $89,995

                        $670/mo*

                        Austin, TX 78735 | South Austin Marine - Lakeside

                        2018 Bennington 25 R

                        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 22 MSB

                        $92,970

                        $693/mo*

                        Lake Havasu City, AZ 86403 | Sun Country Marine Group

                        2026 Bennington 22 MSB
                        • 2026 Bennington 22 SSB

                          $62,938

                          $469/mo*

                          Port Orange, FL 32127 | Blue Water Marine Port Orange

                          2026 Bennington 22 SSB
                          • 2026 Bennington 22 SSB

                            $62,937

                            $469/mo*

                            Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                            2026 Bennington 22 SSB

                            2026 Bennington 22 MSB

                            $90,516

                            $674/mo*

                            Lake Havasu City, AZ 86403 | Sun Country Marine Group

                            2026 Bennington 22 MSB
                            • 2025 Bennington 22 MFB

                              $79,893

                              $595/mo*

                              Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                              2025 Bennington 22 MFB
                              • 2026 Bennington 20SLSE

                                $59,891

                                $446/mo*

                                Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                                2026 Bennington 20SLSE

                                2026 Bennington 20SXSNP REAR FISH

                                $49,995

                                $435/mo*

                                Waco, TX 76710 | Yowells Boat Yard Inc.

                                2026 Bennington 20SXSNP REAR FISH

                                2026 Bennington 24 MSL

                                $115,994

                                $864/mo*

                                Costa Mesa, CA 92614 | Sun Country Marine Group

                                2026 Bennington 24 MSL
                                • 2026 Bennington 20 S STERN RADIUS

                                  $59,446

                                  $443/mo*

                                  Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                                  2026 Bennington 20 S STERN RADIUS

                                  2026 Bennington 26 MSB

                                  $128,083

                                  $954/mo*

                                  Lake Havasu City, AZ 86403 | Sun Country Marine Group

                                  2026 Bennington 26 MSB

                                  2026 Bennington 20SXSNP REAR FISH

                                  $49,995

                                  $435/mo*

                                  Waco, TX 76710 | Yowells Boat Yard Inc.

                                  2026 Bennington 20SXSNP REAR FISH

                                  2026 Bennington 26 MCSB

                                  $134,885

                                  $1,005/mo*

                                  Lake Havasu City, AZ 86403 | Sun Country Marine Group

                                  2026 Bennington 26 MCSB

                                  2026 Bennington 26 MCSB

                                  $135,299

                                  $1,008/mo*

                                  Costa Mesa, CA 92614 | Sun Country Marine Group

                                  2026 Bennington 26 MCSB
                                  • 2026 Bennington 20 SSR

                                    $39,972

                                    $348/mo*

                                    Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                                    2026 Bennington 20 SSR
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