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  • ECLIPSE

Eclipse, Cobra Python, Evolve, Chesapeake, Bennington boats for sale

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1,771 more Makes...
Bennington Models
  • 22 SSR SPS
  • S Quad Bench 22 SSR
  • 22 SSB SPS
  • 22 SSR
  • M Quad Bench 24 MFB Tritoon
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1,030 more Models...
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  • 58 Chesapeake Boats Inc.
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  • 206 Razor
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    2,363 boats
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      • 2025 Bennington 25RSXBWASE

        $189,838

        $1,386/mo*

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

        • 2025 Bennington 25RSXBWASE
        • 2025 Bennington 25RSXBWASE
        • 2025 Bennington 25RSXBWASE
        • 2025 Bennington 25RSXBWASE
        • 2025 Bennington M Quad Bench 22 MFB Tritoon

          $74,404

          $543/mo*

          Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

          • 2025 Bennington M Quad Bench 22 MFB Tritoon
          • 2025 Bennington M Quad Bench 22 MFB Tritoon
          • 2025 Bennington M Quad Bench 22 MFB Tritoon
          • 2025 Bennington M Quad Bench 22 MFB Tritoon

          2025 Bennington 24 MSB ESP

          $105,988

          $774/mo*

          Dadeville, AL 36853 | Harbor Pointe Sales & Service

          • 2025 Bennington 24 MSB ESP
          • 2025 Bennington 24 MSB ESP
          • 2025 Bennington 24 MSB ESP
          • 2025 Bennington 24 MSB ESP
          • 2025 Bennington M Swingback 24 MSB Tritoon

            $89,812

            $656/mo*

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

            • 2025 Bennington M Swingback 24 MSB Tritoon
            • 2025 Bennington M Swingback 24 MSB Tritoon
            • 2025 Bennington M Swingback 24 MSB Tritoon
            • 2025 Bennington M Swingback 24 MSB Tritoon

            2025 Bennington 24 MFB SPS PLUS

            Request a Price

            Lewisville, US 75067 | Phil Dill Boats

            • 2025 Bennington 24 MFB SPS PLUS
            • 2025 Bennington 24 MFB SPS PLUS
            • 2025 Bennington 24 MFB SPS PLUS
            • 2025 Bennington 24 MFB SPS PLUS

            2026 Bennington 24 MFBSF

            $104,004

            ↓ Price Drop

            $760/mo*

            Round Lake, IL 60073 | Munson Ski & Marine

            • 2026 Bennington 24 MFBSF
            • 2026 Bennington 24 MFBSF
            • 2026 Bennington 24 MFBSF
            • 2026 Bennington 24 MFBSF
            • 2026 Bennington M Quad Bench 26 MSL Tritoon

              $159,238

              $1,163/mo*

              Wayzata, MN 55391 | River Valley Marine – Lake Minnetonka

              • 2026 Bennington M Quad Bench 26 MSL Tritoon
              • 2026 Bennington M Quad Bench 26 MSL Tritoon
              • 2026 Bennington M Quad Bench 26 MSL Tritoon
              • 2026 Bennington M Quad Bench 26 MSL Tritoon

              2026 Bennington 22 SSRSE

              $75,777

              $553/mo*

              Round Lake, IL 60073 | Munson Ski & Marine

              • 2026 Bennington 22 SSRSE
              • 2026 Bennington 22 SSRSE
              • 2026 Bennington 22 SSRSE
              • 2026 Bennington 22 SSRSE

              2026 Bennington 22 SSRSF

              $58,750

              $429/mo*

              Round Lake, IL 60073 | Munson Ski & Marine

              • 2026 Bennington 22 SSRSF
              • 2026 Bennington 22 SSRSF
              • 2026 Bennington 22 SSRSF
              • 2026 Bennington 22 SSRSF
              • 2015 Cobra Python

                $155,000

                $1,132/mo*

                Lake Havasu City, AZ 86406 | Private Seller

                • 2015 Cobra Python
                • 2015 Cobra Python
                • 2015 Cobra Python
                • 2015 Cobra Python
                • 2026 Bennington QX Quad Bench 25 QXFBWA

                  Request a Price

                  Dubuque, IA 52001 | Hawkeye Boat Sales

                  • 2026 Bennington QX Quad Bench 25 QXFBWA
                  • 2026 Bennington QX Quad Bench 25 QXFBWA
                  • 2026 Bennington QX Quad Bench 25 QXFBWA
                  • 2026 Bennington QX Quad Bench 25 QXFBWA

                  2023 Bennington 20 SXL

                  $37,220

                  ↓ Price Drop

                  $319/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 Sun Tracker Bass Buggy 16 XL Select

                  $28,190

                  $242/mo*

                  Columbus, OH 43224 | Sizzle Marine

                  • 2026 Sun Tracker Bass Buggy 16 XL Select
                  • 2026 Sun Tracker Bass Buggy 16 XL Select
                  • 2026 Sun Tracker Bass Buggy 16 XL Select
                  • 2026 Sun Tracker Bass Buggy 16 XL Select

                  2025 Sun Tracker SportFish 20 DLX

                  $40,000

                  $343/mo*

                  Columbus, OH 43224 | Sizzle Marine

                  • 2025 Sun Tracker SportFish 20 DLX
                  • 2025 Sun Tracker SportFish 20 DLX
                  • 2025 Sun Tracker SportFish 20 DLX
                  • 2025 Sun Tracker SportFish 20 DLX

                  2026 Sun Tracker Party Barge 20 DLX

                  $44,475

                  $381/mo*

                  Columbus, OH 43224 | Sizzle Marine

                  • 2026 Sun Tracker Party Barge 20 DLX
                  • 2026 Sun Tracker Party Barge 20 DLX
                  • 2026 Sun Tracker Party Barge 20 DLX
                  • 2026 Sun Tracker Party Barge 20 DLX

                  2023 Bennington 20 SXL

                  $37,220

                  ↓ Price Drop

                  $319/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 SSB Swing Back

                  $41,749

                  $358/mo*

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

                  • 2026 Bennington 20 SSB Swing Back
                  • 2026 Bennington 20 SSB Swing Back
                  • 2026 Bennington 20 SSB Swing Back
                  • 2026 Bennington 20 SSB Swing Back
                  • 2025 Bennington 24 MSB Arch Swingback Tri-Toon Pontoon

                    $124,999

                    $913/mo*

                    Bismarck, ND 58504 | Vallely Sport & Marine - Bismarck

                    • 2025 Bennington 24 MSB Arch Swingback Tri-Toon Pontoon
                    • 2025 Bennington 24 MSB Arch Swingback Tri-Toon Pontoon
                    • 2025 Bennington 24 MSB Arch Swingback Tri-Toon Pontoon
                    • 2025 Bennington 24 MSB Arch Swingback Tri-Toon Pontoon
                    • 2002 Chesapeake Bay Built

                      $75,000

                      Deale, MD 20751 | Private Seller

                      • 2002 Chesapeake Bay Built
                      • 2002 Chesapeake Bay Built
                      • 2002 Chesapeake Bay Built
                      • 2002 Chesapeake Bay Built
                      • 2026 Bennington 20 SSR

                        $44,443

                        $381/mo*

                        Port Orange, FL 32127 | Blue Water Marine Port Orange

                        • 2026 Bennington 20 SSR
                        • 2026 Bennington 20 SSR
                        • 2026 Bennington 20 SSR
                        • 2026 Bennington 20 SSR

                        2025 Bennington 25 RXSB

                        $168,703

                        $1,232/mo*

                        Sarasota, FL 34238 | Ingman Marine- Sarasota

                        • 2025 Bennington 25 RXSB
                        • 2025 Bennington 25 RXSB
                        • 2025 Bennington 25 RXSB
                        • 2025 Bennington 25 RXSB
                        • 2025 Bennington 25 QSBA ESP Custom 400HP V10 Tritoon Pontoon

                          $219,999

                          $1,607/mo*

                          Minot, ND 58701 | Vallely Sport & Marine - Minot

                          • 2025 Bennington 25 QSBA ESP Custom 400HP V10 Tritoon Pontoon
                          • 2025 Bennington 25 QSBA ESP Custom 400HP V10 Tritoon Pontoon
                          • 2025 Bennington 25 QSBA ESP Custom 400HP V10 Tritoon Pontoon
                          • 2025 Bennington 25 QSBA ESP Custom 400HP V10 Tritoon Pontoon

                          2026 Bennington 21 S SWINGBACK

                          $68,479

                          $500/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

                          2026 Bennington 23 SSB Swing Back Pontoon

                          $53,249

                          $389/mo*

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

                          • 2026 Bennington 23 SSB Swing Back Pontoon
                          • 2026 Bennington 23 SSB Swing Back Pontoon
                          • 2026 Bennington 23 SSB Swing Back Pontoon
                          • 2026 Bennington 23 SSB Swing Back Pontoon
                          • 2025 Bennington 21 SSR Quad Bench (In Stock)

                            $42,499

                            $364/mo*

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

                            • 2025 Bennington 21 SSR Quad Bench (In Stock)
                            • 2025 Bennington 21 SSR Quad Bench (In Stock)
                            • 2025 Bennington 21 SSR Quad Bench (In Stock)
                            • 2025 Bennington 21 SSR Quad Bench (In Stock)

                            2026 Bennington 24 MSB

                            Request a Price

                            Sarasota, FL 34238 | Ingman Marine- Sarasota

                            • 2026 Bennington 24 MSB
                            • 2026 Bennington 24 MSB
                            • 2026 Bennington 24 MSB
                            • 2026 Bennington 24 MSB
                            • 2026 Bennington 20 S STERN RADIUS

                              $45,729

                              $392/mo*

                              Fleming Island, FL 32003 | Bluewater Marine Fleming Island

                              • 2026 Bennington 20 S STERN RADIUS
                              • 2026 Bennington 20 S STERN RADIUS
                              • 2026 Bennington 20 S STERN RADIUS
                              • 2026 Bennington 20 S STERN RADIUS

                              2026 Bennington 24 MS

                              Request a Price

                              Sarasota, FL 34238 | Ingman Marine- Sarasota

                              • 2026 Bennington 24 MS
                              • 2026 Bennington 24 MS
                              • 2026 Bennington 24 MS
                              • 2026 Bennington 24 MS

                              2026 Bennington 25 QXFBWA ESP

                              Request a Price

                              Ft. Myers, FL 33908 | Marina Mikes

                              • 2026 Bennington 25 QXFBWA ESP
                              • 2026 Bennington 25 QXFBWA ESP
                              • 2026 Bennington 25 QXFBWA ESP
                              • 2026 Bennington 25 QXFBWA ESP

                              2015 Bennington R23

                              $34,995

                              ↓ Price Drop

                              $300/mo*

                              Pompano Beach, FL 33064 | The Boat Kings

                              • 2015 Bennington R23
                              • 2015 Bennington R23
                              • 2015 Bennington R23
                              • 2015 Bennington R23
                              • 2014 Chesapeake 46 Trawler

                                $175,000

                                $1,278/mo*

                                Stuart, FL 34994 | HMY Yacht Sales, Inc.

                                • 2014 Chesapeake 46 Trawler
                                • 2014 Chesapeake 46 Trawler
                                • 2014 Chesapeake 46 Trawler
                                • 2014 Chesapeake 46 Trawler

                                2025 Bennington 27 QSBAX2 ESP

                                Request a Price

                                Lewisville, US 75067 | Phil Dill Boats

                                • 2025 Bennington 27 QSBAX2 ESP
                                • 2025 Bennington 27 QSBAX2 ESP
                                • 2025 Bennington 27 QSBAX2 ESP
                                • 2025 Bennington 27 QSBAX2 ESP

                                2024 Bennington 22 SVSR SPS

                                $49,995

                                $428/mo*

                                Conroe, US 77384 | SMG Boats

                                • 2024 Bennington 22 SVSR SPS
                                • 2024 Bennington 22 SVSR SPS
                                • 2024 Bennington 22 SVSR SPS
                                • 2024 Bennington 22 SVSR SPS
                                • 2024 Bennington 20 SVF

                                  $39,850

                                  $341/mo*

                                  Hayden, ID 83835 | Tobler Marina

                                  • 2024 Bennington 20 SVF
                                  • 2024 Bennington 20 SVF
                                  • 2024 Bennington 20 SVF
                                  • 2024 Bennington 20 SVF
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