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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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    4,075 boats
    Sort: Recommended
    • Recommended
    • Recently Updated: Newest first
    • Recently Updated: Oldest first
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      2026 Lagoon EIGHTY 2

      Request a Price

      Charleston, SC 29401 | The Multihull Company

      2026 Lagoon EIGHTY 2
      Dealer Logo

      1934 Custom Schooner

      $865,000

      $6,639/mo*

      Port Angeles, WA 98362 | Seacraft Yacht Sales, Inc

      1934 Custom Schooner
      Dealer Logo

      1989 Custom Schooner Liveaboard

      $95,000

      $729/mo*

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

      1989 Custom Schooner Liveaboard
      Dealer Logo
      • 2007 Hunter 27

        $29,950

        $267/mo*

        Buford, GA 30518 | Snug Harbor Boats

        2007 Hunter 27
        • 2006 Leopard 40

          $199,000

          $1,527/mo*

          Saint Simons Island, GA | Just Catamarans

          2006 Leopard 40
          • 1995 PDQ 32 LRC

            $65,000

            Miami Beach, FL | Just Catamarans

            1995 PDQ 32 LRC
            • 2002 Alerion Express 28

              $64,900

              Orleans, MA 02647 | K. McCann Yacht Sales

              2002 Alerion Express 28

              2000 Voyage Yachts 440

              $239,999

              ↓ Price Drop

              Fort Lauderdale, FL 33004 | Just Catamarans

              2000 Voyage Yachts 440

              1989 Custom Schooner Liveaboard

              $95,000

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

              1989 Custom Schooner Liveaboard

              2016 Dufour 382 Grand Large

              $139,000

              $1,067/mo*

              Annapolis, MD 21403 | ACY Yachts

              2016 Dufour 382 Grand Large

              2027 Dragonfly 36

              $698,905

              $5,364/mo*

              Pensacola, FL 32507 | Windcraft Multihulls

              2027 Dragonfly 36
              • 2002 Hunter 380

                $49,000

                Rock Hall, MD 21661 | Salt Yacht Brokerage Company

                2002 Hunter 380
                • 1989 Island Packet 38

                  $79,900

                  Solomons, MD 20688 | Adventure Yacht Sales

                  1989 Island Packet 38

                  1986 Cape Dory MS300

                  $29,000

                  Fort Myers, FL 33901 | Grand Slam Yacht Sales Inc.

                  1986 Cape Dory MS300
                  • 2026 Bali 4.2

                    $524,763

                    $4,028/mo*

                    Hollywood, FL 33020 | Catamaran Gurus

                    2026 Bali 4.2
                    • 1988 Island Packet 38

                      $109,900

                      Pensacola, FL 32501 | Edwards Yacht Sales

                      1988 Island Packet 38

                      2000 Hunter 290

                      $19,000

                      ↓ Price Drop

                      St Petersburg, FL 33701 | Adventure Yacht Sales

                      2000 Hunter 290

                      2013 Jeanneau Sun Odyssey 44 DS

                      $251,000

                      ↓ Price Drop

                      $1,926/mo*

                      Seattle, WA 98109 | Marine Servicenter - Seattle

                      2013 Jeanneau Sun Odyssey 44 DS
                      • 1989 Cape Dory 27

                        $19,500

                        Island Heights, NJ 08732 | Jersey Cape Yacht Sales

                        1989 Cape Dory 27
                        • 2008 Hunter 27

                          $39,800

                          $355/mo*

                          Eureka, CA 95503 | Rubicon Yachts- San Rafael

                          2008 Hunter 27
                          • 1976 Allied Seawind II

                            $15,000

                            Tarpon Springs, FL 33617 | Private Seller

                            1976 Allied Seawind II
                            • 2019 Lagoon 42

                              $379,000

                              $2,909/mo*

                              Fort Lauderdale, FL 33301 | The Multihull Company

                              2019 Lagoon 42

                              2005 Lagoon 440

                              $215,000

                              ↓ Price Drop

                              Charleston, SC 29401 | The Multihull Company

                              2005 Lagoon 440

                              1986 Covey Island 38

                              $49,500

                              Eliot, ME 03903 | Merri-Mar Yacht Basin, Inc

                              1986 Covey Island 38

                              1979 Bristol 29.9

                              $11,900

                              ↓ Price Drop

                              Barrinton, RI | The Cruising Yacht Brokerage, LLC

                              1979 Bristol 29.9
                              • 1986 Stephens Deck Saloon

                                $325,000

                                Portsmouth, RI 02871 | David Walters Yachts

                                1986 Stephens Deck Saloon
                                • 2007 Leopard 46

                                  $399,000

                                  $3,062/mo*

                                  Key West, FL 33040 | The Multihull Company

                                  2007 Leopard 46
                                  • 1983 Thackwray Custom Pilothouse Motorsailer

                                    $649,000

                                    Wrangell, AK 99929 | Chuck Hovey Yachts, Inc.

                                    1983 Thackwray Custom Pilothouse Motorsailer

                                    1997 J Boats J/42

                                    $169,000

                                    Harpswell, ME 04079 | Sailboats Northeast

                                    1997 J Boats J/42

                                    1985 Custom 60

                                    $190,000

                                    West Palm Beach, FL 33407 | McNally Yacht Sales

                                    1985 Custom 60
                                    • 1990 Slocum 43

                                      $124,500

                                      Fort Pierce, FL 34950 | United Yacht Sales - Florida, Merritt Island

                                      1990 Slocum 43
                                      • 2005 Gemini 105Mc

                                        $83,500

                                        Saint James, NC 28461 | Private Seller

                                        2005 Gemini 105Mc

                                        2010 Hanse 545

                                        $315,000

                                        $2,418/mo*

                                        Portsmouth, RI 02871 | Northstar Yacht Sales, LLC

                                        2010 Hanse 545
                                        • 1978 Newport 16

                                          $3,500

                                          Buford, GA 30518 | Snug Harbor Boats

                                          1978 Newport 16
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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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