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Highfield Classic Sloop Sailboats for sale

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233 more Makes...
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6 more Models...
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    149 boats
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    • Price: High to Low
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      • 2024 Highfield Classic 380 GT

        Request a Price

        West Palm Beach, FL 33412 | Nautical Ventures

        2024 Highfield Classic 380 GT
        • 2024 Highfield Classic 360 FCT

          Request a Price

          West Palm Beach, FL 33412 | Nautical Ventures

          2024 Highfield Classic 360 FCT
          • 2023 Highfield Classic 460

            Request a Price

            Naples, ME 04055 | Moose Landing Marina

            2023 Highfield Classic 460
            • 2022 Highfield Classic 340 FCT

              $13,995

              Clearwater, FL 33760 | Suncoast Inflatables

              2022 Highfield Classic 340 FCT

              2025 Highfield Classic 310

              $6,199

              Annapolis, MD 21403 | Annapolis Inflatables

              2025 Highfield Classic 310
              • 2023 Highfield Classic 380 GT

                $25,995

                $226/mo*

                Clearwater, FL 33760 | Suncoast Inflatables

                2023 Highfield Classic 380 GT

                2025 Highfield Classic 260

                Request a Price

                Annapolis, MD 21403 | Annapolis Inflatables

                2025 Highfield Classic 260

                2024 Highfield Classic 340

                $4,820

                Shelburne, VT 05482 | Small Boat Exchange

                2024 Highfield Classic 340
                • 2025 Highfield Classic 420

                  $34,250

                  $298/mo*

                  Marshfield, MA 02050 | McShane Yacht Sales

                  2025 Highfield Classic 420
                  • 2024 Highfield Classic 340 GT

                    $22,995

                    Clearwater, FL 33760 | Suncoast Inflatables

                    2024 Highfield Classic 340 GT
                    • 2025 Highfield Classic 340 FCT

                      $19,595

                      Clearwater, FL 33760 | Suncoast Inflatables

                      2025 Highfield Classic 340 FCT
                      • 2025 Highfield Classic 310 FCT

                        $17,595

                        Clearwater, FL 33760 | Suncoast Inflatables

                        2025 Highfield Classic 310 FCT
                        • 2025 Highfield Classic 340 FCT

                          $19,595

                          Clearwater, FL 33760 | Suncoast Inflatables

                          2025 Highfield Classic 340 FCT

                          2026 Yamaha Boats AR220

                          $60,999

                          $454/mo*

                          Columbus, OH 43224 | Sizzle Marine

                          2026 Yamaha Boats AR220

                          2026 Tracker Pro Team 175

                          $29,595

                          $258/mo*

                          Columbus, OH 43224 | Sizzle Marine

                          2026 Tracker Pro Team 175

                          2026 Sun Tracker Fishin' Barge 20 DLX

                          $45,410

                          $395/mo*

                          Columbus, OH 43224 | Sizzle Marine

                          2026 Sun Tracker Fishin' Barge 20 DLX

                          2025 Highfield Classic 380

                          $22,499

                          Harrison Twp, MI 48045 | Keenan Marina

                          2025 Highfield Classic 380
                          • 2024 Highfield Classic 460

                            $17,100

                            Clearwater, FL 33760 | Suncoast Inflatables

                            2024 Highfield Classic 460

                            2025 Highfield Classic 340

                            Request a Price

                            Annapolis, MD 21403 | Annapolis Inflatables

                            2025 Highfield Classic 340
                            • 2025 Highfield Classic 340 GT

                              $22,995

                              Clearwater, FL 33760 | Suncoast Inflatables

                              2025 Highfield Classic 340 GT

                              2025 Highfield Classic 400

                              $26,950

                              $235/mo*

                              Harrison Twp, MI 48045 | Keenan Marina

                              2025 Highfield Classic 400
                              • 2024 Highfield Classic 360 FCT

                                $19,995

                                Clearwater, FL 33760 | Suncoast Inflatables

                                2024 Highfield Classic 360 FCT

                                2025 Highfield Classic 380

                                $22,499

                                Harrison Twp, MI 48045 | Keenan Marina

                                2025 Highfield Classic 380
                                • 2024 Highfield Classic 380 FCT

                                  $20,995

                                  Clearwater, FL 33760 | Suncoast Inflatables

                                  2024 Highfield Classic 380 FCT
                                  • 2025 Highfield Classic 340

                                    $21,900

                                    Harrison Twp, MI 48045 | Keenan Marina

                                    2025 Highfield Classic 340
                                    • 2024 Highfield Classic 360 GT

                                      $24,995

                                      Clearwater, FL 33760 | Suncoast Inflatables

                                      2024 Highfield Classic 360 GT
                                      • 2024 Highfield Classic 380 GT

                                        $25,995

                                        $226/mo*

                                        Clearwater, FL 33760 | Suncoast Inflatables

                                        2024 Highfield Classic 380 GT
                                        • 2025 Highfield Classic 380

                                          $9,694

                                          Clearwater, FL 33760 | Suncoast Inflatables

                                          2025 Highfield Classic 380
                                          • 2025 Highfield Classic 400

                                            $30,995

                                            $270/mo*

                                            Clearwater, FL 33760 | Suncoast Inflatables

                                            2025 Highfield Classic 400
                                            • 2021 Highfield Classic 290

                                              $5,995

                                              Clearwater, FL 33760 | Suncoast Inflatables

                                              2021 Highfield Classic 290
                                              • 2025 Highfield Classic 400

                                                $14,246

                                                Clearwater, FL 33760 | Suncoast Inflatables

                                                2025 Highfield Classic 400
                                                • 2025 Highfield Classic 400

                                                  $31,750

                                                  $276/mo*

                                                  Marshfield, MA 02050 | McShane Yacht Sales

                                                  2025 Highfield Classic 400

                                                  2025 Highfield Classic 310

                                                  $6,614

                                                  Clearwater, FL 33760 | Suncoast Inflatables

                                                  2025 Highfield Classic 310
                                                  • 2023 Highfield Classic 360

                                                    $9,694

                                                    Clearwater, FL 33760 | Suncoast Inflatables

                                                    2023 Highfield Classic 360
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