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    Within 100 Miles Of
    Marco Island, Florida

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Sailboat boats for sale in Marco Island Florida

There are 14 new and used Sailboat boats for sale in Marco Island, Florida. Explore Sailboat brands like Bristol, Catalina, Other, Beneteau, 2 Bar, and CSY on BoatCrazy. View a wide selection of Sailboat boats from $14,500 to $99,000.
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  • Boats
  • Sailboat
    Within 100 Miles Of
    Marco Island, Florida
14 boats found within 100 miles from Marco Island, Florida
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  • 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
  • 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
  • Price Drop 1979 CSY 37 Plan A Shoal

    1979 CSY 37 Plan A Shoal

    $15,000
    Cape Coral, FL
    • Cape Coral, FL
    • Sailboat
    • 37'
    • 1979 / Used
    • $15,000

    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
    $15,000
    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
  • Price Drop 1992 Other Tropic 1200

    1992 Other Tropic 1200

    $45,000
    Placida, FL
    • Placida, FL
    • Sailboat
    • 42'
    • 1992 / Used
    • $45,000

    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
    $45,000
    VIEW DETAILS
  • Price Drop 1980 Morgan 461

    1980 Morgan 461

    $54,500
    Port Charlotte, FL
    • Port Charlotte, FL
    • Sailboat
    • 46'
    • 1980 / Used
    • $54,500

    Stock #499782 Reason for selling is "Sellers sailing adventures are over for now". This Morgan has now been on the market more than a month. Please submit your offer today! Grea... View Details

    View 10 Photos and Details Contact Seller
    $54,500
    VIEW DETAILS
  • 2023 2 Bar 62

    2023 2 Bar 62

    $70,700
    Miami, FL
    • Miami, FL
    • Sailboat
    • 20'
    • 2023 / New
    • $70,700

    The 2.Bar 6.20 is a cutting-edge and dynamic boat designed for a wide range of boating activities. Its compact size and agile design make it a versatile option for both adventurous... View Details

    View 25 Photos and Details Contact Seller
    $70,700
    VIEW DETAILS
  • 1982 C & C 43 Landfall

    1982 C & C 43 Landfall

    $83,900
    Marathon, FL
    • Marathon, FL
    • Sailboat
    • 43'
    • 1982 / Used
    • $83,900

    Stock #435883 Video of this vessel available at www [dot] popsells [dot] com/view/435883 Reason for selling is "Seller wants a smaller sailboat". ANY and ALL offers will be put... View Details

    View 10 Photos and Details Contact Seller
    $83,900
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  • Price Drop 2011 Beneteau OCEANIS 40

    2011 Beneteau OCEANIS 40

    $99,000
    Marathon, FL
    • Marathon, FL
    • Sailboat
    • 40'
    • 2011 / Used
    • $99,000

    Stock #485961 Video of this vessel available at www [dot] popsells [dot] com/view/485961 Reason for selling is "Not using enough". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $99,000
    VIEW DETAILS
  • 1967 Bristol 39

    1967 Bristol 39

    $15,000
    Marathon, FL

    Bristol 39 Sailboat - A Timeless Classic for the Avid Sailor Step aboard the Bristol 39, a classic cruiser that embodies the elegance and craftsmanship of the golden age of sailin... View Details

    View 9 Photos and Details Contact Seller
    $15,000
    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
  • Price Drop 2003 Catalina 350 MKI Wing Keel

    2003 Catalina 350 MKI Wing Keel

    $84,900
    Islamorada, FL
    • Islamorada, FL
    • Sailboat
    • 35'
    • 2003 / Used
    • $84,900

    Stock #494632 Video of this vessel available at www [dot] popsells [dot] com/view/494632 Reason for selling is "RV travel plans". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $84,900
    VIEW DETAILS
  • 1983 Bristol 31.1

    1983 Bristol 31.1

    $25,000
    Dania, FL
    • Dania, FL
    • Sailboat
    • 31'
    • 1983 / Used
    • $25,000

    Stock #509164 This is a new advertisement, on the market just this week (Oct 22nd). Always accepting offers! The Bristol 31.1 is a well-respected offshore cruising sailboat desig... View Details

    View 1 Photo and Details Contact Seller
    $25,000
    VIEW DETAILS
  • Price Drop 1987 Ericson 35.3 STD

    1987 Ericson 35.3 STD

    $22,000
    Key Largo, FL
    • Key Largo, FL
    • Sailboat
    • 35'
    • 1987 / Used
    • $22,000

    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
    $22,000
    VIEW DETAILS
Showing 1 to 14 of 14 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.