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    Within 100 Miles Of
    Sarasota, Florida

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Sailboat boats for sale in Sarasota Florida

There are 12 new and used Sailboat boats for sale in Sarasota, Florida. Explore Sailboat brands like Catalina, Other, CSY, Custom Built, Gulfstar, and Hunter on BoatCrazy. View a wide selection of Sailboat boats from $12,500 to $147,000.
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  • Sailboat
    Within 100 Miles Of
    Sarasota, Florida
12 boats found within 100 miles from Sarasota, Florida
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  • Price Drop 1993 Catalina 270

    1993 Catalina 270

    $12,500
    Bradenton, FL
    • Bradenton, FL
    • Sailboat
    • 27' / 0'
    • 1993 / Used
    • $12,500

    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
    $12,500
    VIEW DETAILS
  • 1973 Gulfstar 44

    1973 Gulfstar 44

    $49,000
    Ruskin, FL
    • Ruskin, FL
    • Sailboat
    • 44' / 0'
    • 1973 / Used
    • $49,000

    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
    $49,000
    VIEW DETAILS
  • 1996 Hunter 40.5 Legend

    1996 Hunter 40.5 Legend

    $49,900
    Ruskin, FL
    • Ruskin, FL
    • Sailboat
    • 40' / 0'
    • 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

    View 10 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • Price Drop 1993 Custom Built Baraka 46

    1993 Custom Built Baraka 46

    $69,875
    Saint Petersburg, FL
    • Saint Petersburg, FL
    • Sailboat
    • 46' / 14'
    • 1993 / Used
    • $69,875

    1993 Custom 46’ Baraka CutterESME is a custom-built 46’ cutter that has just returned from an approximately nine-month family cruise through the Caribbean and to Panama, a real-wor... View Details

    View 25 Photos and Details Contact Seller
    $69,875
    VIEW DETAILS
  • 1992 Other Tropic 1200

    1992 Other Tropic 1200

    $65,000
    Placida, FL
    • Placida, FL
    • Sailboat
    • 42' / 0'
    • 1992 / Used
    • $65,000

    Stock #438378 Video of this vessel available at www [dot] popsells [dot] com/view/438378 Reason for selling is "No longer using". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $65,000
    VIEW DETAILS
  • 1989 Morgan 44 Center Cockpit

    1989 Morgan 44 Center Cockpit

    $62,000
    Tampa, FL
    • Tampa, FL
    • Sailboat
    • 44' / 0'
    • 1989 / Used
    • $62,000

    Stock #474817 Video of this vessel available at www [dot] popsells [dot] com/view/474817 Reason for selling is "Not currently Using". This Morgan has now been on the market a co... View Details

    View 10 Photos and Details Contact Seller
    $62,000
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  • 1998 Island Packet 40

    1998 Island Packet 40

    $147,000
    Punta Gorda, FL
    • Punta Gorda, FL
    • Sailboat
    • 41' / 0'
    • 1998 / Used
    • $147,000

    1998 Island Packet 40 (Original Owner)Ground tackle:Lighthouse 1501 electric windlass with dual chain gypsy and rope capstanDeck power up and down windlass foot switchesShurflo pro... View Details

    View 111 Photos and Details Contact Seller
    $147,000
    VIEW DETAILS
  • Price Drop 2000 Catalina 36 MKII

    2000 Catalina 36 MKII

    $35,000
    Dunedin, FL
    • Dunedin, FL
    • Sailboat
    • 36' / 0'
    • 2000 / Used
    • $35,000

    Stock #438188 Video of this vessel available at www [dot] popsells [dot] com/view/438188 Reason for selling is "Ready for the happy new owner". ANY and ALL offers will be put in... View Details

    View 11 Photos and Details Contact Seller
    $35,000
    VIEW DETAILS
  • 1989 Other H-28

    1989 Other H-28

    $19,000
    Bokeelia, FL
    • Bokeelia, FL
    • Sailboat
    • 29' / 0'
    • 1989 / Used
    • $19,000

    Stock #481612 Reason for selling is "Life changes". This is a new advertisement, on the market just this week (Mar 31st). Always accepting offers! CUTE, COZY, CLASSIC, WELL LOVE... View Details

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    $19,000
    VIEW DETAILS
  • Price Drop 1979 CSY 37 Plan A Shoal

    1979 CSY 37 Plan A Shoal

    $29,900
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 37' / 0'
    • 1979 / Used
    • $29,900

    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
    $29,900
    VIEW DETAILS
  • 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' / 0'
    • 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

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    $56,000
    VIEW DETAILS
  • Price Drop 1988 Catalina 30

    1988 Catalina 30

    $15,000
    Hudson, FL
    • Hudson, FL
    • Sailboat
    • 30' / 10'
    • 1988 / Used
    • $15,000

    The 1988 Catalina 30 is a classic cruising sailboat that has long been appreciated for its combination of performance, comfort, and affordability. With a length overall (LOA) of 30... View Details

    View 24 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
Showing 1 to 12 of 12 boats found.

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 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.