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  • - Stock #195971 - Customized Pearson Countess 44 with aft canopy and dingy davits! (dingy not included) If you are in the market for a sloop, look no further than this 1966 Pea... View Details

    $39,900
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  • - Stock #161060 - 35.5C combine the classic design of Ted Hood with the meticulous craftsmanship of Bristol Yachts in a comfortable and elegant cruiser-racer! If you are in the... View Details

    $39,500
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  • - Stock #223555 - Well Equipped Canadian Sailcraft 36, Ready to Cruise, Bring Offers! If you are in the market for a sloop, look no further than this 1983 Canadian Sailcraft CS... View Details

    $39,500
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  • The First 375 is a race boat but comportable sleeps 4 to 6 people. It was designed by Jean Berret with a long history of trophies. Yet I have sailed her single handed on many trips... View Details

    $39,000
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  • This Hunter 326 is a FRESH WATER, one-owner cruiser. It is ready for daysailing or open water adventures. There is 6'5" headroom, sleeps 6 in three separate cabins. Propane Stove,... View Details

    $39,000
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  • - Stock #230582 - Lots of Updates!! Blue Water Ready!! Solid Experienced Cruiser!! If you are in the market for a ketch, look no further than this 1977 Allied Princess 36, pric... View Details

    $38,900
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  • - Stock #190121 - Excellent family cruiser with many upgrades. New Doyle Main, Raymarine GPS/Autopilot! 3 Varying Size Jibs! Asymetrical Spinnaker! If you are in the market for... View Details

    $38,900
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  • - Stock #197600 - Comfortable Cruiser Spacious interior cabin. Great for a couple cruising sailboat or single handled with AUTO PILOT If you are in the market for a sloop, look... View Details

    $38,900
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  • - Stock #208435 - This one is a proven sailor -- The boat can take it if the new Captain can If you are in the market for a cruiser, look no further than this 1977 Morgan 33 Ou... View Details

    $38,900
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  • - Stock #227435 - Excellent proven coastal or Bluewater cruiser! Equipped with navigation electronics! Plenty of storage! New upgrades! Ready to cruise! If you are in the marke... View Details

    $38,500
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  • Easy to trailer, Cruiser model with pop top, 2080 lbs, dry, water ballast, roller furling genoa, main and genoa in good condition. Harken winches and windward sheeting main travele... View Details

    $38,000
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  • - Stock #208121 - WOW!!! Teak Everywhere! Tons of Character! A Truly Stunning Vessel!!! If you are in the market for a cutter, look no further than this 1979 Union (Taiwan) Pol... View Details

    $38,000
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  • - Stock #223664 - Beautiful Islander, Cruise the Caribbean without to make a passage to get there If you are in the market for a sloop, look no further than this 1968 Islander... View Details

    $38,000
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  • - Stock #232729 - Winthrop Warner designed Acadia Ketch, A classic, eye-catching, well maintained ketch sailed only in freshwater! If you are in the market for a ketch, look no... View Details

    $37,900
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  • An extremely well-maintained example of the very popular Hunter 336 Sailboat…Stara. She’s USCG registered and equipped with many of the best factory options furling jib AND main,... View Details

    $37,500
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  • - Stock #207217 - Custom Built racer. Custom Lifting Bulb Keel Schock hull custom built for Offshore Racing! Will trade! If you are in the market for a racer, look no further t... View Details

    $36,500
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  • - Stock #198094 - 1981 TAYANA 37 CUTTER SAILBOAT 42' LOA PERKINS DIESEL If you are in the market for a cutter, look no further than this 1981 Tayana 37 CUTTER, priced right at... View Details

    $35,600
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  • - Stock #221587 - 36' Cutter teak with varnish, updated UK Main & new main sail cover, newer bimini/dodger & connector w/side curtains! If you are in the market for a cutter, l... View Details

    $35,600
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  • - Stock #216271 - Nice and Solid 1983 Endeavour 35! Ready to sail! If you are in the market for a cruiser, look no further than this 1983 Endeavour 35, just reduced to $35,000... View Details

    $35,000
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  • - Stock #233765 - Wee Seal 20 designed by Ian Oughtred, Dabbler sails, bronze hardware, Ian's Big Rig, 5 hp Mercury outboard, double axle trailer! If you are in the market for... View Details

    $35,000
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  • - Stock #192190 - Westsail 32, built strong very strong and solid, started the cruising boom, one of the most seaworthy vessels designed! If you are in the market for a cutter,... View Details

    $35,000
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Showing 169 to 189 of 449 boats found.

Sailboat Boats On Boatcrazy

Sailboats harness wind power for propulsion, offering an eco-friendly and serene boating experience. They come in various types, including sloops, ketches, and catamarans, each with distinct sail configurations. Sizes range from small dinghies to large yachts equipped for ocean crossings. Sailboats are popular for recreational cruising, racing, and liveaboard lifestyles. They require knowledge of wind patterns, navigation, and sail handling, providing an engaging experience for enthusiasts.

Sailboat boats for sale by State