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Sailboat boats for sale in Florida

There are 104 new and used boats for sale in Florida. Find boats of all types and price ranges on BoatCrazy.com. We offer boats for sale by owner and dealers. Browse through Fishing Boats, Center Consoles, Pontoons, Cruisers, PWCs and more in Florida.
104 boats found within 200 miles out of 8,147 Boats Found

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  • 1974 Morgan 41 Out Island

    1974 Morgan 41 Out Island

    $55,600
    Moore Haven, FL
    • Moore Haven, FL
    • Sailboat
    • 41' / 0'
    • 1974 / Used
    • $55,600

    - Stock #226576 - Bottom paint, all new sails, new bilge pump, never used solar panels, and all new varnish on the woodwork inside. If you are in the market for a ketch, look n... View Details

    View 10 Photos and Details Contact Seller
    $55,600
    VIEW DETAILS
  • 1978 Tayana 37

    1978 Tayana 37

    $50,000
    Fort Myers Beach, FL
    • Fort Myers Beach, FL
    • Sailboat
    • 37' / 0'
    • 1978 / Used
    • $50,000

    - Stock #233709 - Ready to go sailing!! Solid wood cabin and head doors throughout the vessel!! Raymarine speed log!! Raymarine depth sounder and much more included!!! If you a... View Details

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    $50,000
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  • 2010 Other 26RK

    2010 Other 26RK

    $49,999
    Marathon, FL
    • Marathon, FL
    • Sailboat
    • 26' / 0'
    • 2010 / Used
    • $49,999

    The Seaward 26RK is a recreational keelboat, built predominantly of fiberglass, with wood trim. The deck is cored with Divinycell foam for weight . What make this differe... View Details

    View 11 Photos and Details Contact Seller
    $49,999
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  • 1982 Beneteau First 38

    1982 Beneteau First 38

    $49,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 38' / 0'
    • 1982 / Used
    • $49,900

    - Stock #177967 - Bluewater Cruise Ready!! Just Prep-Splash-Go!! Perkins 4-108 Diesel Engine!! Him If you are in the market for a sloop, look no further than this 1982 Beneteau... View Details

    View 10 Photos and Details Contact Seller
    $49,900
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  • 1987 Bayfield 36 Cutter

    1987 Bayfield 36 Cutter

    $48,000
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 36' / 0'
    • 1987 / Used
    • $48,000

    - Stock #220705 - 36 ft of Luxury on Water! Solid, Sturdy and Comfortable Blue Water Cruiser. The Captain's Quarters is Stunning! If you are in the market for a cutter, look no... View Details

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    $48,000
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  • 1984 Endeavour E33

    1984 Endeavour E33

    $47,000
    Saint Petersburg, FL
    • Saint Petersburg, FL
    • Sailboat
    • 33' / 0'
    • 1984 / Used
    • $47,000

    - Stock #229642 - Electric Drive! $80,000 Refit! Tons of Solar! Watermaker! Dinghy! Shoal Draft! Perfect Cruiser/Liveaboard! If you are in the market for a cruiser, look no fur... View Details

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    $47,000
    VIEW DETAILS
  • 1983 Morgan Out Island 41

    1983 Morgan Out Island 41

    $45,000
    Placida, FL
    • Placida, FL
    • Sailboat
    • 41' / 0'
    • 1983 / Used
    • $45,000

    - Stock #194091 - Classic Morgan Design! Center-cockpit! Perfect live-aboard or cruiser! Ready for the next adventurer! If you are in the market for a ketch, look no further th... View Details

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    $45,000
    VIEW DETAILS
  • 1980 Nor Sea 27

    1980 Nor Sea 27

    $44,995
    Satellite Beach, FL
    • Satellite Beach, FL
    • Sailboat
    • 27' / 0'
    • 1980 / Used
    • $44,995

    - Stock #215511 - Beautiful and well maintained 1980 Nor'sea 27! Ready to sail! If you are in the market for a cruiser, look no further than this 1980 Nor'sea Marine 27, just r... View Details

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    $44,995
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  • 1981 Lancer 42

    1981 Lancer 42

    $44,950
    Sarasota, FL
    • Sarasota, FL
    • Sailboat
    • 42' / 0'
    • 1981 / Used
    • $44,950

    - Stock #196384 - Great Condition, Diesel, Located in Dominican Republic If you are in the market for a sloop, look no further than this 1981 Lancer 42, just reduced to $44,950... View Details

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    $44,950
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  • 2006 Bruce Roberts Spray 40

    2006 Bruce Roberts Spray 40

    $44,900
    Hudson, FL
    • Hudson, FL
    • Sailboat
    • 40' / 0'
    • 2006 / Used
    • $44,900

    - Stock #182236 - Blue water solid 40 foot Cutter that takes your breath away! If you are in the market for a cutter, look no further than this 2006 Bruce Roberts Spray 40, jus... View Details

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    $44,900
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  • 1988 Catalina 34

    1988 Catalina 34

    $44,500
    Marathon, FL
    • Marathon, FL
    • Sailboat
    • 34' / 0'
    • 1988 / Used
    • $44,500

    - Stock #215193 - Shoal Draft Model! Accommodations have always been a strong selling point for all Catalina models, and the 34 is no different. If you are in the market for a... View Details

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    $44,500
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  • 2001 Hunter 320

    2001 Hunter 320

    $43,900
    Satellite Beach, FL
    • Satellite Beach, FL
    • Sailboat
    • 32' / 0'
    • 2001 / Used
    • $43,900

    - Stock #229888 - 2001 HUNTER 320 coastal cruiser, very comfortable and easy to sail! If you are in the market for a sloop, look no further than this 2001 Hunter 320, priced ri... View Details

    View 10 Photos and Details Contact Seller
    $43,900
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  • 2003 Catalina 310

    2003 Catalina 310

    $41,000
    Stuart, FL
    • Stuart, FL
    • Sailboat
    • 31' / 0'
    • 2003 / Used
    • $41,000

    - Stock #231006 - ***SALE PENDING*** 2020 Major refit ~ Remanufactured Engine New Head Sail - Refurbished Main Sail - Recovered interior cushions - New Head, Macerator & Bimini... View Details

    View 10 Photos and Details Contact Seller
    $41,000
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  • 1981 Choate 44

    1981 Choate 44

    $40,000
    Key West, FL
    • Key West, FL
    • Sailboat
    • 44' / 0'
    • 1981 / Used
    • $40,000

    - Stock #165200 - 1981 Choate 44 SPECIAL RARE SOLIDLY CONSTRUCTED RACER/CRUISER! If you are in the market for a cutter, look no further than this 1981 Choate 44, just reduced t... View Details

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    $40,000
    VIEW DETAILS
  • 1989 Capital Gulf 29 Pilot

    1989 Capital Gulf 29 Pilot

    $40,000
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 29' / 0'
    • 1989 / Used
    • $40,000

    - Stock #232033 - READY TO SAIL! Rare Gulf Pilot 29, with inside Pilot house. OUTSTANDING CONDITION If you are in the market for a cruiser, look no further than this 1989 Capit... View Details

    View 10 Photos and Details Contact Seller
    $40,000
    VIEW DETAILS
  • 1987 Irwin 43-CC MK III

    1987 Irwin 43-CC MK III

    $39,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 43' / 0'
    • 1987 / Used
    • $39,900

    - Stock #216833 - Needs Some Love But Has All The Bones to Be a Great Boat Again!! Motivated seller is looking for offers on an "as is" sale. If you are in the market for a slo... View Details

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    $39,900
    VIEW DETAILS
  • 1977 Morgan 33 Out Island

    1977 Morgan 33 Out Island

    $38,900
    Key West, FL
    • Key West, FL
    • Sailboat
    • 33' / 0'
    • 1977 / Used
    • $38,900

    - 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

    View 10 Photos and Details Contact Seller
    $38,900
    VIEW DETAILS
  • 1986 Hunter 34

    1986 Hunter 34

    $38,900
    Fort Lauderdale, FL
    • Fort Lauderdale, FL
    • Sailboat
    • 34' / 0'
    • 1986 / Used
    • $38,900

    - 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

    View 10 Photos and Details Contact Seller
    $38,900
    VIEW DETAILS
  • 1968 Islander 44

    1968 Islander 44

    $38,000
    Sarasota, FL
    • Sarasota, FL
    • Sailboat
    • 44' / 0'
    • 1968 / Used
    • $38,000

    - 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

    View 10 Photos and Details Contact Seller
    $38,000
    VIEW DETAILS
  • 1995 Hunter 336

    1995 Hunter 336

    $37,500
    Merritt Island, FL
    • Merritt Island, FL
    • Sailboat
    • 33' / 11'
    • 1995 / Used
    • $37,500

    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

    View 12 Photos and Details Contact Seller
    $37,500
    VIEW DETAILS
  • 1984 Schock 35 Custom Racer

    1984 Schock 35 Custom Racer

    $36,500
    Bradenton, FL
    • Bradenton, FL
    • Sailboat
    • 35' / 0'
    • 1984 / Used
    • $36,500

    - 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

    View 10 Photos and Details Contact Seller
    $36,500
    VIEW DETAILS
Showing 22 to 42 of 104 boats found.
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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.

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