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Sailboat boats for sale in Florida

There are 37 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.
37 boats found within 200 miles out of 14,830 Boats Found

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  • 2002 Hunter 326 Cruiser

    2002 Hunter 326 Cruiser

    $39,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 32' / 0'
    • 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
  • 1976 Morgan Out Island 41

    1976 Morgan Out Island 41

    $39,000
    Islamorada, FL
    • Islamorada, FL
    • Sailboat
    • 41' / 0'
    • 1976 / Used
    • $39,000

    Stock #478744 This is a new advertisement, on the market just this week (Jan 30th). Always accepting offers! 1976 Morgan Out Island 41 Ketch with an Updated Kubota Diesel,New Tra... View Details

    View 10 Photos and Details Contact Seller
    $39,000
    VIEW DETAILS
  • 1997 Hunter 310

    1997 Hunter 310

    $35,000
    Panama City, FL
    • Panama City, FL
    • Sailboat
    • 31' / 0'
    • 1997 / Used
    • $35,000

    Stock #478590 This is a new advertisement, on the market just this week (Feb 9th). Always accepting offers! 1997 Hunter 310 sloop rigged sailing vessel powered by a Yanmar diesel... View Details

    View 2 Photos and Details Contact Seller
    $35,000
    VIEW DETAILS
  • Price Drop 1974 Gulfstar 41 Ketch

    1974 Gulfstar 41 Ketch

    $35,000
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 41' / 0'
    • 1974 / Used
    • $35,000

    Stock #429648 Video of this vessel available at www [dot] popsells [dot] com/view/429648 Reason for selling is "Done Sailing for Now". ANY and ALL offers will be put in front of... View Details

    View 10 Photos and Details Contact Seller
    $35,000
    VIEW DETAILS
  • Price Drop 1981 Ericson 38

    1981 Ericson 38

    $33,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 38' / 0'
    • 1981 / Used
    • $33,900

    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! Add Bottom Paint and This One Is Ready To... View Details

    View 10 Photos and Details Contact Seller
    $33,900
    VIEW DETAILS
  • 1987 Ericson 35.3 STD

    1987 Ericson 35.3 STD

    $33,000
    Key Largo, FL
    • Key Largo, FL
    • Sailboat
    • 35' / 0'
    • 1987 / Used
    • $33,000

    Stock #454770 Video of this vessel available at www [dot] popsells [dot] com/view/454770 Reason for selling is "Upgrading to a catamaran". This Ericson Yachts has been on the ma... View Details

    View 10 Photos and Details Contact Seller
    $33,000
    VIEW DETAILS
  • 1979 CSY 37 Plan A Shoal

    1979 CSY 37 Plan A Shoal

    $32,000
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 37' / 0'
    • 1979 / Used
    • $32,000

    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
    $32,000
    VIEW DETAILS
  • Price Drop 1979 O Day 37 Mid-Cockpit

    1979 O Day 37 Mid-Cockpit

    $23,500
    Key Largo, FL
    • Key Largo, FL
    • Sailboat
    • 37' / 0'
    • 1979 / Used
    • $23,500

    Stock #448042 Reason for selling is "Downsizing". ANY and ALL offers will be put in front of our seller! Submit your offer today! Fully off grid, complete solar system. 240 gal... View Details

    View 10 Photos and Details Contact Seller
    $23,500
    VIEW DETAILS
  • 2021 Flying Scot 19

    2021 Flying Scot 19

    $23,000
    Sarasota, FL
    • Sarasota, FL
    • Sailboat
    • 19' / 0'
    • 2021 / Used
    • $23,000

    Stock #459151 Reason for selling is "Not Using enough". ANY and ALL offers will be put in front of our seller! Submit your offer today! Well maintained 2021 Flying Scot 19 sailb... View Details

    View 10 Photos and Details Contact Seller
    $23,000
    VIEW DETAILS
  • 1982 CAL 35

    1982 CAL 35

    $21,900
    Palm City, FL
    • Palm City, FL
    • Sailboat
    • 35' / 0'
    • 1982 / Used
    • $21,900

    Stock #442837 Reason for selling is "Done Sailing". ANY and ALL offers will be put in front of our seller! Submit your offer today! Well equipped 1982 Cal 35! This sailboat has... View Details

    View 10 Photos and Details Contact Seller
    $21,900
    VIEW DETAILS
  • 1993 Catalina 270

    1993 Catalina 270

    $20,750
    Bradenton, FL
    • Bradenton, FL
    • Sailboat
    • 27' / 0'
    • 1993 / Used
    • $20,750

    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
    $20,750
    VIEW DETAILS
  • 1988 Catalina 30

    1988 Catalina 30

    $19,000
    Hudson, FL
    • Hudson, FL
    • Sailboat
    • 30' / 10'
    • 1988 / Used
    • $19,000

    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
    $19,000
    VIEW DETAILS
  • Price Drop 1984 Island Packet 26 MKII

    1984 Island Packet 26 MKII

    $16,900
    Naples, FL
    • Naples, FL
    • Sailboat
    • 26' / 0'
    • 1984 / Used
    • $16,900

    Stock #426351 Video of this vessel available at www [dot] popsells [dot] com/view/426351 Reason for selling is "Has too many boats". ANY and ALL offers will be put in front of o... View Details

    View 10 Photos and Details Contact Seller
    $16,900
    VIEW DETAILS
  • 1973 Bristol 35

    1973 Bristol 35

    $15,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 35' / 0'
    • 1973 / Used
    • $15,900

    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
    $15,900
    VIEW DETAILS
  • Price Drop 1978 Herreshoff Meadowlark 37

    1978 Herreshoff Meadowlark 37

    $15,000
    Bradenton, FL
    • Bradenton, FL
    • Sailboat
    • 37' / 0'
    • 1978 / Used
    • $15,000

    Stock #445947 Reason for selling is "Moved out of area". ANY and ALL offers will be put in front of our seller! Submit your offer today! L. Francis Herreshoff Design! Shoal draf... View Details

    View 10 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • Price Drop 2015 Coral 16 RIBS

    2015 Coral 16 RIBS

    $14,999
    Miami, FL
    • Miami, FL
    • Sailboat
    • 16' / 0'
    • 2015 / Used
    • $14,999

    Blue Ribs 40HP Suzuki 2023 - 5 hours Trailer Sound System Lights Fiberglass Floor Ladder Perfect and Ready to Sail View Details

    View 16 Photos and Details Contact Seller
    $14,999
    VIEW DETAILS
Showing 22 to 37 of 37 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 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.

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.