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Sailboat boats for sale in Florida

There are 61 new and used Sailboat boats for sale in Florida. Explore Sailboat brands like Jeanneau, Beneteau, Other, Lagoon, Morgan, and Dufour on BoatCrazy. View a wide selection of Sailboat boats from $1,700 to $850,000.
61 boats found within 100 miles out of 11,817 Boats Found
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  • 1995 Catalina 36 Mark II Shoal Draft

    1995 Catalina 36 Mark II Shoal Draft

    $56,000
    Fort Myers Beach, FL
    • Fort Myers Beach, FL
    • Sailboat
    • 36'
    • 1995 / Used
    • $56,000

    Stock #339883 Reason for selling is "Upgrading". ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautiful Catalina MK II Shoal Draft Wing Keel,... View Details

    View 10 Photos and Details Contact Seller
    $56,000
    VIEW DETAILS
  • 2003 Dufour 34

    2003 Dufour 34

    $55,000
    Miami, FL
    • Miami, FL
    • Sailboat
    • 10'
    • 2003 / Used
    • $55,000

    DUFOUR 34 2 cabines Moteur Volvo Penta MD2030 Batterie moteur neuve Régulateur de consommation électrique Convertisseur électrique Pilote automatique + télécommande Compteur de... View Details

    View 25 Photos and Details Contact Seller
    $55,000
    VIEW DETAILS
  • 1979 Pearson 40

    1979 Pearson 40

    $55,000
    Miami, FL
    • Miami, FL
    • Sailboat
    • 40'
    • 1979 / Used
    • $55,000

    Stock #306233 Video of this vessel available at www [dot] popsells [dot] com/view/306233 Reason for selling is "Looking to go bigger". ANY and ALL offers will be put in front of... View Details

    View 10 Photos and Details Contact Seller
    $55,000
    VIEW DETAILS
  • 1993 Beneteau First 35.5

    1993 Beneteau First 35.5

    $52,200
    Melbourne, FL
    • Melbourne, FL
    • Sailboat
    • 35'
    • 1993 / Used
    • $52,200

    Stock #454865 Reason for selling is "not using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Elegant And Fast 1993 Beneteau First 35.5 Racer/... View Details

    View 10 Photos and Details Contact Seller
    $52,200
    VIEW DETAILS
  • 1975 Other 24

    1975 Other 24

    $50,000
    Miami, FL
    • Miami, FL
    • Sailboat
    • 24'
    • 1975 / Used
    • $50,000

    J24 for sale View Details

    View 1 Photo and Details Contact Seller
    $50,000
    VIEW DETAILS
  • 1996 Hunter 40.5 Legend

    1996 Hunter 40.5 Legend

    $49,900
    Ruskin, FL
    • Ruskin, FL
    • Sailboat
    • 40'
    • 1996 / Used
    • $49,900

    Stock #451919 Reason for selling is "Sellers are done with boating for now". ANY and ALL offers will be put in front of our seller! Submit your offer today! Newer sails! Generat... View Details

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    $49,900
    VIEW DETAILS
  • 1973 Gulfstar 44

    1973 Gulfstar 44

    $44,500
    Ruskin, FL
    • Ruskin, FL
    • Sailboat
    • 44'
    • 1973 / Used
    • $44,500

    Stock #339042 Video of this vessel available at www [dot] popsells [dot] com/view/339042 Reason for selling is "Change in life priorities". ANY and ALL offers will be put in fro... View Details

    View 10 Photos and Details Contact Seller
    $44,500
    VIEW DETAILS
  • 1990 Herreshoff 37 Diddikai

    1990 Herreshoff 37 Diddikai

    $44,350
    Marco Island, FL
    • Marco Island, FL
    • Sailboat
    • 37'
    • 1990 / Used
    • $44,350

    Stock #391951 Video of this vessel available at www [dot] popsells [dot] com/view/391951 Reason for selling is "Moving to Canada". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $44,350
    VIEW DETAILS
  • 1967 Morgan 34

    1967 Morgan 34

    $40,000
    Crystal River, FL
    • Crystal River, FL
    • Sailboat
    • 34'
    • 1967 / Used
    • $40,000

    Stock #133855 Reason for selling is "No time to use". ANY and ALL offers will be put in front of our seller! Submit your offer today! Popular Morgan 34! 1967 Morgan 34 for sale... View Details

    View 10 Photos and Details Contact Seller
    $40,000
    VIEW DETAILS
  • 2002 Hunter 326 Cruiser

    2002 Hunter 326 Cruiser

    $39,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 32'
    • 2002 / Used
    • $39,900

    Stock #391868 Video of this vessel available at www [dot] popsells [dot] com/view/391868 Reason for selling is "Not Using". ANY and ALL offers will be put in front of our seller... View Details

    View 10 Photos and Details Contact Seller
    $39,900
    VIEW DETAILS
  • 1982 Beneteau First 28

    1982 Beneteau First 28

    $30,000
    Miami, FL
    • Miami, FL
    • Sailboat
    • 9'
    • 1982 / Used
    • $30,000

    Équilibre et performance. Conçu par l'architecte J.M. Finot, le First 28 s'inscrit parfaitement dans la lignée des First : des bateaux rapides et sûrs. Les entrées pincées et les f... View Details

    View 14 Photos and Details Contact Seller
    $30,000
    VIEW DETAILS
  • 1976 Morgan Out Island 41

    1976 Morgan Out Island 41

    $30,000
    Islamorada, FL
    • Islamorada, FL
    • Sailboat
    • 41'
    • 1976 / Used
    • $30,000

    Stock #478744 ANY and ALL offers will be put in front of our seller! Submit your offer today! 1976 Morgan Out Island 41 Ketch with an Updated Kubota Diesel,New Transmissio If yo... View Details

    View 10 Photos and Details Contact Seller
    $30,000
    VIEW DETAILS
  • Price Drop 1987 Ericson 35.3 STD

    1987 Ericson 35.3 STD

    $26,500
    Key Largo, FL
    • Key Largo, FL
    • Sailboat
    • 35'
    • 1987 / Used
    • $26,500

    Stock #454770 Video of this vessel available at www [dot] popsells [dot] com/view/454770 Reason for selling is "Upgrading to a catamaran". ANY and ALL offers will be put in fron... View Details

    View 10 Photos and Details Contact Seller
    $26,500
    VIEW DETAILS
  • Price Drop 1981 Ericson 38

    1981 Ericson 38

    $24,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 38'
    • 1981 / Used
    • $24,900

    Stock #449972 Reason for selling is "No Longer Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Bruce King-designed Ericson 38 with solar,... View Details

    View 10 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 1979 CSY 37 Plan A Shoal

    1979 CSY 37 Plan A Shoal

    $24,900
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 37'
    • 1979 / Used
    • $24,900

    Stock #450629 Reason for selling is "Not Using Enough". ANY and ALL offers will be put in front of our seller! Submit your offer today! Nice blue water sailor! Updated Electroni... View Details

    View 10 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • Price Drop 1989 Other H-28

    1989 Other H-28

    $14,500
    Bokeelia, FL
    • Bokeelia, FL
    • Sailboat
    • 29'
    • 1989 / Used
    • $14,500

    Stock #481612 Reason for selling is "Life changes". ANY and ALL offers will be put in front of our seller! Submit your offer today! CHARMING, COZY, CLASSIC, WELL LOVED PARKINS H... View Details

    View 10 Photos and Details Contact Seller
    $14,500
    VIEW DETAILS
  • 1973 Bristol 35

    1973 Bristol 35

    $14,000
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 35'
    • 1973 / Used
    • $14,000

    Stock #409107 Video of this vessel available at www [dot] popsells [dot] com/view/409107 Reason for selling is "Not Using". ANY and ALL offers will be put in front of our seller... View Details

    View 10 Photos and Details Contact Seller
    $14,000
    VIEW DETAILS
  • Price Drop 1993 Catalina 270

    1993 Catalina 270

    $9,995
    Bradenton, FL
    • Bradenton, FL
    • Sailboat
    • 27'
    • 1993 / Used
    • $9,995

    Stock #439087 Video of this vessel available at www [dot] popsells [dot] com/view/439087 Reason for selling is "Have Another sailboat". ANY and ALL offers will be put in front o... View Details

    View 10 Photos and Details Contact Seller
    $9,995
    VIEW DETAILS
  • Price Drop 1973 Macgregor Venture 21

    1973 Macgregor Venture 21

    $1,700
    Stuart, FL
    • Stuart, FL
    • Sailboat
    • 21'
    • 1973 / Used
    • $1,700

    1973 MacGregor 21' Sailboat – Includes 2020 Tohatsu 6HP & 2004 Trailer – As-Is 1973 MacGregor 21-foot sailboat project boat. The boat is in poor condition and is... View Details

    View 2 Photos and Details Contact Seller
    $1,700
    VIEW DETAILS
Showing 43 to 61 of 61 boats found.
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Sailboat boats for sale in Florida by City

Most Common Boat Searches in Florida

Sailboat Boats on Boatcrazy

As the name suggests, sailboats rely partly or entirely on the power of the wind for propulsion and use large cloth or synthetic sails for this purpose.

We have many kinds of Sailboats for Sale and as they differ by use, size and strength – it’s important to consider carefully which type of sailboat is best for your intended use.

Sailboat Boats manufacturers on Boatcrazy

When looking to buy a quality Sailboat consider these top Sailboat Manufacturers

Hallberg-Rassy, Dufour, Beneteau, Brewer, Bluewater, Irwin, Herve, Endeavour, Corsair, Sabre, Hardin, Gulfstar, Willard.

Sailboat boats for sale in Florida by State

Sailboat Boats Frequently Asked Questions

How much does an average Sailboat cost?

Cruising sailboat prices vary. The average cost of new cruising sailboats is about $250K; however they range from around 100k all the way up to 500k. For used models you should expect an expense between 10k-100k.

To date, the average price for sailboat insurance has been around $250 to $1500 per year. This varies based on what type of policy and how much coverage you need - but it's usually cheaper than power boat insurance!

Obviously, the best time to buy a Sailboat is when the time is right for your budget! But there is never a bad time, as long as you are ready to handle the responsibility of owning such a boat, and on Boatcrazy, we have plenty to choose from! Each season also has its advantages and disadvantages, so understanding what each season presents can be of great help in finding a better deal.

Cruising Sailboats are the ultimate way to explore long distances, but for a Sailboat to travel a long journey, the boat needs to be livable, should have the right amenities and plenty of storage space, and should be able to travel at a decent speed. Moreover, it should be strong and durable.

Sailing through the Indian Ocean has come to be a challenging task owing to its characteristic of being one of the most deadly ocean waters in the world for Sailboats.

Centerboards are an essential part of any boat, but they're especially important on smaller vessels that don't have the weight or power to self-propel. Centerboard equipped boats range in length from 12 - 25 feet and work as both stability and steering systems.