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Highfield Sloop Sailboats for sale

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    508 boats
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      • 2025 Highfield Ultralite 310

        Request a Price

        Fort Lauderdale, FL 33316 | Nautical Ventures

        2025 Highfield Ultralite 310
        • 2025 Highfield Sport 660

          Request a Price

          Apalachicola, FL 32328 | Nautical Ventures

          2025 Highfield Sport 660
          • 2024 Highfield Classic 380 FCT

            Request a Price

            Stuart, FL 34994 | Nautical Ventures

            2024 Highfield Classic 380 FCT
            • 2025 Highfield Sport 560

              $71,804

              $535/mo*

              Weymouth, MA 02188 | Monahan's Marine

              2025 Highfield Sport 560

              2023 Highfield Sport 330

              Request a Price

              Fort Lauderdale, FL 33316 | Nautical Ventures

              2023 Highfield Sport 330
              • 2024 Highfield Classic 420

                Request a Price

                Apalachicola, FL 32328 | Nautical Ventures

                2024 Highfield Classic 420
                • 2025 Highfield Ultralite 310

                  Request a Price

                  Stuart, FL 34994 | Nautical Ventures

                  2025 Highfield Ultralite 310
                  • 2025 Highfield Classic 340

                    $7,910

                    Weymouth, MA 02188 | Monahan's Marine

                    2025 Highfield Classic 340
                    • 2025 Highfield UltraLite 290SS

                      Request a Price

                      Fort Lauderdale, FL 33316 | Nautical Ventures

                      2025 Highfield UltraLite 290SS
                      • 2025 Highfield Ultralite 240LT

                        Request a Price

                        Apalachicola, FL 32328 | Nautical Ventures

                        2025 Highfield Ultralite 240LT
                        • 2025 Highfield Sport 660

                          Request a Price

                          Stuart, FL 34994 | Nautical Ventures

                          2025 Highfield Sport 660
                          • 2024 Highfield UltraLite 290LT

                            Request a Price

                            Fort Lauderdale, FL 33316 | Nautical Ventures

                            2024 Highfield UltraLite 290LT
                            • 2025 Highfield Classic 310

                              $7,010

                              Weymouth, MA 02188 | Monahan's Marine

                              2025 Highfield Classic 310

                              2026 Tracker Grizzly 14 Jon

                              $2,170

                              Columbus, OH 43224 | Sizzle Marine

                              2026 Tracker Grizzly 14 Jon

                              2025 Tracker Grizzly 1236 Utility

                              $1,670

                              Columbus, OH 43224 | Sizzle Marine

                              2025 Tracker Grizzly 1236 Utility

                              2025 Tracker Grizzly 1236 Utility

                              $1,670

                              Columbus, OH 43224 | Sizzle Marine

                              2025 Tracker Grizzly 1236 Utility
                              • 2024 Highfield Patrol 460

                                Request a Price

                                Apalachicola, FL 32328 | Nautical Ventures

                                2024 Highfield Patrol 460
                                • 2025 Highfield Sport 330

                                  Request a Price

                                  Stuart, FL 34994 | Nautical Ventures

                                  2025 Highfield Sport 330
                                  • 2024 Highfield Classic 360 FCT

                                    Request a Price

                                    Fort Lauderdale, FL 33316 | Nautical Ventures

                                    2024 Highfield Classic 360 FCT
                                    • 2024 Highfield Classic 460

                                      Request a Price

                                      Apalachicola, FL 32328 | Nautical Ventures

                                      2024 Highfield Classic 460
                                      • 2025 Highfield Sport 520

                                        Request a Price

                                        Stuart, FL 34994 | Nautical Ventures

                                        2025 Highfield Sport 520

                                        2025 Highfield Sport 330

                                        Request a Price

                                        Fort Lauderdale, FL 33316 | Nautical Ventures

                                        2025 Highfield Sport 330
                                        • 2025 Highfield Ultralite 240SS

                                          Request a Price

                                          Apalachicola, FL 32328 | Nautical Ventures

                                          2025 Highfield Ultralite 240SS
                                          • 2024 Highfield Classic 340 GT

                                            Request a Price

                                            Stuart, FL 34994 | Nautical Ventures

                                            2024 Highfield Classic 340 GT
                                            • 2025 Highfield Sport 420

                                              Request a Price

                                              Fort Lauderdale, FL 33316 | Nautical Ventures

                                              2025 Highfield Sport 420
                                              • 2025 Highfield Sport 650

                                                Request a Price

                                                Apalachicola, FL 32328 | Nautical Ventures

                                                2025 Highfield Sport 650
                                                • 2025 Highfield Sport 700

                                                  Request a Price

                                                  Stuart, FL 34994 | Nautical Ventures

                                                  2025 Highfield Sport 700
                                                  • 2025 Highfield Sport 390

                                                    Request a Price

                                                    Fort Lauderdale, FL 33316 | Nautical Ventures

                                                    2025 Highfield Sport 390
                                                    • 2025 Highfield Classic 460

                                                      $39,326

                                                      $342/mo*

                                                      Weymouth, MA 02188 | Monahan's Marine

                                                      2025 Highfield Classic 460
                                                      • 2025 Highfield Ultralite 220SS

                                                        Request a Price

                                                        Apalachicola, FL 32328 | Nautical Ventures

                                                        2025 Highfield Ultralite 220SS
                                                        • 2024 Highfield Patrol 600

                                                          Request a Price

                                                          Stuart, FL 34994 | Nautical Ventures

                                                          2024 Highfield Patrol 600
                                                          • 2022 Highfield Sport 420

                                                            $27,000

                                                            $235/mo*

                                                            Fort Lauderdale, FL 33316 | Nautical Ventures

                                                            2022 Highfield Sport 420
                                                            • 2025 Highfield Sport 390

                                                              Request a Price

                                                              Apalachicola, FL 32328 | Nautical Ventures

                                                              2025 Highfield Sport 390

                                                              2024 Highfield Classic 340

                                                              $7,600

                                                              Weymouth, MA 02188 | Monahan's Marine

                                                              2024 Highfield Classic 340
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