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  • Sail

Sailboats for sale

Boats propelled partly or entirely by sails including a variety of sailing boats or yachts in terms of size, dimension and configuration of sails of the vessel.
Read our helpful guide to Sailboats
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    3,658 boats
    Sort: Recommended
    • Recommended
    • Recently Updated: Newest first
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      2026 Lagoon EIGHTY 2

      Request a Price

      Kemah, TX 77565 | The Multihull Company

      2026 Lagoon EIGHTY 2
      Dealer Logo

      1999 Custom International Americas Cup Class USCG Certified 20 pax

      $285,000

      $2,103/mo*

      Rio Vista, CA 94571 | Rubicon Yachts

      1999 Custom International Americas Cup Class USCG Certified 20 pax
      Dealer Logo

      1977 Custom 80 Brigantine

      $1,350,000

      $9,962/mo*

      Long Beach, CA 90802 | Rick Obey Yacht Sales

      1977 Custom 80 Brigantine
      Dealer Logo
      • 1989 Custom Schooner Liveaboard

        $95,000

        Shady Side, MD 20778 | YachtSalesInternational.Com -Martin Bird Associates

        1989 Custom Schooner Liveaboard
        • 1994 Beneteau Oceanis 400

          $45,000

          Miami, FL 33133 | Private Seller

          1994 Beneteau Oceanis 400
          • 1994 Hinckley Sou'wester 42 Sloop

            $295,000

            Southwest Harbor, ME 04679 | Hinckley Yacht Brokerage

            1994 Hinckley Sou'wester 42 Sloop

            2008 Catalina 309

            $59,995

            $443/mo*

            Kemah, TX 77565 | Jarman Yacht Sales, LLC

            2008 Catalina 309
            • 2002 Alerion Express 28

              $64,900

              Orleans, MA 02647 | K. McCann Yacht Sales

              2002 Alerion Express 28

              2019 Lagoon 42

              $379,000

              $2,797/mo*

              Fort Lauderdale, FL 33301 | The Multihull Company

              2019 Lagoon 42

              2005 Corsair F-31 1D

              $94,900

              Stuart, FL 34997 | The Finish Line

              2005 Corsair F-31 1D
              • 2006 Catalina 42 MkII

                $189,000

                $1,395/mo*

                San Diego, CA 92106 | Private Seller

                2006 Catalina 42 MkII
                • 2009 Jeanneau Sun Odyssey 44i

                  $175,000

                  $1,291/mo*

                  Superior, WI 54880 | Barker's Island Marina

                  2009 Jeanneau Sun Odyssey 44i

                  1987 Pearson 36-2

                  $22,000

                  ↓ Price Drop

                  Port Charlotte, FL 33952 | United Yacht Sales

                  1987 Pearson 36-2
                  • 1990 Cheoy Lee Sloop

                    $459,000

                    North Miami Beach, FL 33162 | Atlantic Yacht & Ship, Inc.

                    1990 Cheoy Lee Sloop
                    • 1980 Tayana 37

                      $39,900

                      Deltaville, VA 23043 | YaZu Yachting

                      1980 Tayana 37

                      1990 Custom 46

                      $49,500

                      Seattle, WA 98117 | Seattle Yachts

                      1990 Custom 46

                      2013 Gemini Legacy

                      $145,000

                      ↓ Price Drop

                      $1,070/mo*

                      West Palm Beach, FL 33403 | McNally Yacht Sales

                      2013 Gemini Legacy
                      • 2000 Crowther Catamaran

                        $80,900

                        Dighton, MA 02715 | The Multihull Source

                        2000 Crowther Catamaran
                        • 2015 Beneteau Oceanis 35

                          $149,000

                          $1,100/mo*

                          Marina Bay, CA 94804 | Rubicon Yachts

                          2015 Beneteau Oceanis 35
                          • 1998 Beneteau Oceanis 50

                            $149,000

                            Lantana, FL 33462 | United Yacht Sales

                            1998 Beneteau Oceanis 50

                            2021 Fountaine Pajot Elba 45 Catamaran

                            $699,000

                            ↓ Price Drop

                            $5,158/mo*

                            St Thomas, VI 00802 | ACY Yachts

                            2021 Fountaine Pajot Elba 45 Catamaran

                            1982 Watkins 27 Pirate Ship!

                            $4,999

                            Washington, NC 27889 | McCotters Marina

                            1982 Watkins 27 Pirate Ship!
                            • 1987 Kelly Peterson 46

                              $69,000

                              Fort Lauderdale, FL 33315 | Private Seller

                              1987 Kelly Peterson 46

                              1999 Hunter 380

                              $69,500

                              ↓ Price Drop

                              Bayfield, WI 54817 | Hooper's Yachts

                              1999 Hunter 380
                              • 1987 Hunter Legend 35

                                $19,500

                                Melbourne, FL 32901 | Private Seller

                                1987 Hunter Legend 35
                                • 2003 Leopard 47

                                  $210,000

                                  Fajardo, PR 00773 | The Multihull Company

                                  2003 Leopard 47

                                  1992 Dragonfly 800 Swing Wing

                                  $39,000

                                  ↓ Price Drop

                                  Port Orange, FL 32129 | Windcraft Multihulls

                                  1992 Dragonfly 800 Swing Wing
                                  • 2020 Beneteau Oceanis 30.1

                                    $170,000

                                    $1,254/mo*

                                    Hilton Head Island, SC 29926 | North Point Yacht Sales

                                    2020 Beneteau Oceanis 30.1
                                    • 1998 Catalina 36 MkII

                                      $68,500

                                      Hull, MA 02045 | Eastern Yacht Sales, Inc.

                                      1998 Catalina 36 MkII
                                      • 1995 Island Packet 40

                                        $179,900

                                        Hilton Head Island, SC 29928 | Adventure Yacht Sales

                                        1995 Island Packet 40
                                        • 2006 Gemini Gemini 105 MC

                                          $79,900

                                          $590/mo*

                                          Moore Haven, FL 33471 | Private Seller

                                          2006 Gemini Gemini 105 MC

                                          1996 Blue Water 60 Ketch

                                          $99,000

                                          Fort Lauderdale, FL 33301 | Rick Obey Yacht Sales

                                          1996 Blue Water 60 Ketch

                                          2014 Seaton Custom Ketch

                                          $175,000

                                          ↓ Price Drop

                                          $1,291/mo*

                                          Miami, FL 33133 | Grove Yacht Sales

                                          2014 Seaton Custom Ketch
                                          • 1973 Nautor Swan 44

                                            $99,900

                                            Hingham, MA | K. McCann Yacht Sales

                                            1973 Nautor Swan 44
                                            • 2027 Fountaine Pajot Thira 80

                                              Request a Price

                                              Annapolis, MD 21403 | ACY Yachts Annapolis

                                              2027 Fountaine Pajot Thira 80
                                              Dealer Logo
                                              • 1998 Custom Kelly Archer

                                                $1,290,000

                                                $9,519/mo*

                                                Newport, RI 02840 | ACY Yachts - Marina Del Rey

                                                1998 Custom Kelly Archer
                                                Dealer Logo
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                                              Sailboats

                                              Sailboats

                                              Sailboats are propelled partly or entirely by sails and include a variety of types from cutters to sloops and catboats to schooners. Traditionally sailboats are monohull displacement hulls, but catamarans and multi-hulls are becoming more common. There are many kinds of sailboats and they carry different rigs (masts, supporting shrouds and stay, and sail combinations). Sloops have one mast and generally two sails – a mainsail and a headsail called a jib or genoa. If there are two headsails, the boat is usually called a cutter rig. Ketches have two masts with the aft mast shorter than the main mast. Yawls also have a shorter aft mast but it’s farther back on deck than a ketch. A schooner can have two or three masts with the forward-most one being shorter. Sailboats differ by size, use and strength of build – so it’s important to consider carefully which type of sailboat is best for your intended use. Once you understand the different options available, you can make an educated choice.

                                              Expert Sailboats Reviews

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