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  • 2007 Custom Built 16

    2007 Custom Built 16

    $97,000
    Kansas City, KS
    • Kansas City, KS
    • Sailboat
    • 16' / 0'
    • 2007 / Used
    • $97,000

    Stock #176116 ANY and ALL offers will be put in front of our seller! Submit your offer today! The Little Leon is a scale replica of the Square Sail Brigantine "Leon". She was ent... View Details

    View 4 Photos and Details Contact Seller
    $97,000
    VIEW DETAILS
  • Price Drop 1982 Nauticat 38

    1982 Nauticat 38

    $89,500
    Groton, CT
    • Groton, CT
    • Sailboat
    • 38' / 0'
    • 1982 / Used
    • $89,500

    Stock #427079 Video of this vessel available at www [dot] popsells [dot] com/view/427079 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
    $89,500
    VIEW DETAILS
  • Price Drop 1981 Other 40

    1981 Other 40

    $85,000
    Cathlamet, WA
    • Cathlamet, WA
    • Sailboat
    • 40' / 0'
    • 1981 / Used
    • $85,000

    Stock #413566 Video of this vessel available at www [dot] popsells [dot] com/view/413566 Reason for selling is "Health issues forces sale". ANY and ALL offers will be put in fro... View Details

    View 10 Photos and Details Contact Seller
    $85,000
    VIEW DETAILS
  • Price Drop 2007 Beneteau First 10R

    2007 Beneteau First 10R

    $85,000
    Savannah, GA
    • Savannah, GA
    • Sailboat
    • 33' / 0'
    • 2007 / Used
    • $85,000

    Stock #254117 Video of this vessel available at www [dot] popsells [dot] com/view/254117 ANY and ALL offers will be put in front of our seller! Submit your offer today! Highly s... View Details

    View 10 Photos and Details Contact Seller
    $85,000
    VIEW DETAILS
  • 1985 Endeavour Center Cockpit 42

    1985 Endeavour Center Cockpit 42

    $84,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 42' / 0'
    • 1985 / Used
    • $84,900

    Stock #440400 Video of this vessel available at www [dot] popsells [dot] com/view/440400 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
    $84,900
    VIEW DETAILS
  • 1982 C & C 43 Landfall

    1982 C & C 43 Landfall

    $83,900
    Placida, FL
    • Placida, FL
    • Sailboat
    • 43' / 0'
    • 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
    VIEW DETAILS
  • 1976 Custom Built 50' Yawl

    1976 Custom Built 50' Yawl

    $80,000
    Morro Bay, CA
    • Morro Bay, CA
    • Sailboat
    • 50' / 0'
    • 1976 / Used
    • $80,000

    Stock #276005 ANY and ALL offers will be put in front of our seller! Submit your offer today! Very Unique ONE-of-a-kind, hand-built replica of the "Spray" famously first singleha... View Details

    View 10 Photos and Details Contact Seller
    $80,000
    VIEW DETAILS
  • 1979 Tom Colvin Gazelle

    1979 Tom Colvin Gazelle

    $75,000
    Baltimore, MD
    • Baltimore, MD
    • Sailboat
    • 42' / 11'
    • 1979 / Used
    • $75,000

    A true head-turner, Summer Wind is a classic Tom Colvin Gazelle schooner with a unique junk rig, built tough with 1/4" steel for serious cruising. Designed for adventure, she&rsquo... View Details

    View 19 Photos and Details Contact Seller
    $75,000
    VIEW DETAILS
  • 1984 Bristol 41.1 CC

    1984 Bristol 41.1 CC

    $75,000
    Corpus Christi, TX
    • Corpus Christi, TX
    • Sailboat
    • 41' / 0'
    • 1984 / Used
    • $75,000

    Stock #465455 Video of this vessel available at www [dot] popsells [dot] com/view/465455 This Bristol has now been on the market more than a month. Please submit your offer today... View Details

    View 10 Photos and Details Contact Seller
    $75,000
    VIEW DETAILS
  • 2023 Other 62

    2023 Other 62

    $70,700
    Miami, FL
    • Miami, FL
    • Sailboat
    • 20' / 8'
    • 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
  • 1977 Bluewater 38 Ingrid

    1977 Bluewater 38 Ingrid

    $70,000
    Elfin Cove, AK
    • Elfin Cove, AK
    • Sailboat
    • 38' / 0'
    • 1977 / Used
    • $70,000

    Stock #256281 Reason for selling is "Not Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Refitted for trolling as well as sailing. Full e... View Details

    View 10 Photos and Details Contact Seller
    $70,000
    VIEW DETAILS
  • 1980 Gulfstar Sailmaster 47

    1980 Gulfstar Sailmaster 47

    $67,500
    Gulf Shores, AL
    • Gulf Shores, AL
    • Sailboat
    • 47' / 0'
    • 1980 / Used
    • $67,500

    Stock #448739 Reason for selling is "No time to use anymore". ANY and ALL offers will be put in front of our seller! Submit your offer today! YOUR SAILING FUN AWAITS YOU! LOTS O... View Details

    View 10 Photos and Details Contact Seller
    $67,500
    VIEW DETAILS
  • Price Drop 2003 Hunter 356

    2003 Hunter 356

    $66,400
    Falmouth, ME
    • Falmouth, ME
    • Sailboat
    • 35' / 0'
    • 2003 / Used
    • $66,400

    Stock #373973 Reason for selling is "Sellers are done with sailing for now". ANY and ALL offers will be put in front of our seller! Submit your offer today! Many recent upgrades... View Details

    View 10 Photos and Details Contact Seller
    $66,400
    VIEW DETAILS
  • Price Drop 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
  • 1985 Nauticat 33 Pilothouse

    1985 Nauticat 33 Pilothouse

    $65,000
    Brookings, OR
    • Brookings, OR
    • Sailboat
    • 33' / 0'
    • 1985 / Used
    • $65,000

    Stock #262043 Reason for selling is "Not using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Classic Nauticat33 Ketch Pilothouse with inside... View Details

    View 10 Photos and Details Contact Seller
    $65,000
    VIEW DETAILS
  • Price Drop 2006 Gemini 105MC

    2006 Gemini 105MC

    $64,500
    Marco Island, FL
    • Marco Island, FL
    • Sailboat
    • 34' / 0'
    • 2006 / Used
    • $64,500

    Stock #447715 Video of this vessel available at www [dot] popsells [dot] com/view/447715 Reason for selling is "Moving on to other adventure". ANY and ALL offers will be put in... View Details

    View 10 Photos and Details Contact Seller
    $64,500
    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 This is a new advertisement, on the market just this week (Dec 2nd). Always accepting offers! Custome made mattress in captains quarters and several upgrades includ... View Details

    View 7 Photos and Details Contact Seller
    $62,000
    VIEW DETAILS
  • 1986 Krogen 38 Cutter

    1986 Krogen 38 Cutter

    $60,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 44' / 12'
    • 1986 / Used
    • $60,000

    1986 Krogen Cutter 38"Intrepid"Intrepid has had two owners and has resided on the freshwater of Lake Michigan since 2012. Designed by James S. Krogen and built by Kady-Krogen Yacht... View Details

    View 56 Photos and Details Contact Seller
    $60,000
    VIEW DETAILS
  • 1993 Catalina 42 MKI

    1993 Catalina 42 MKI

    $60,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 42' / 14'
    • 1993 / Used
    • $60,000

    1993 Catalina 42 MKIThis vessel is equipped with a Dodger, Bimini and connector. Refrigerator, VHF, Stereo System have been upgraded. An AIS system and Garmin GPS/Depth Sounder has... View Details

    View 53 Photos and Details Contact Seller
    $60,000
    VIEW DETAILS
  • 1982 Island Trader 40

    1982 Island Trader 40

    $59,900
    Oakley, CA
    • Oakley, CA
    • Sailboat
    • 40' / 0'
    • 1982 / Used
    • $59,900

    Stock #338527 ANY and ALL offers will be put in front of our seller! Submit your offer today! 1982 Island Trader 40 powered with a Lehman diesel engine These Island Traders were... View Details

    View 10 Photos and Details Contact Seller
    $59,900
    VIEW DETAILS
  • Price Drop 1994 Hunter Legend 40.5

    1994 Hunter Legend 40.5

    $59,900
    Puerto Real, PR
    • Puerto Real, PR
    • Sailboat
    • 40' / 0'
    • 1994 / Used
    • $59,900

    Stock #450385 Reason for selling is "Getting out of Sailing". ANY and ALL offers will be put in front of our seller! Submit your offer today! Well-equipped 1994 Hunter 40 Legend... View Details

    View 9 Photos and Details Contact Seller
    $59,900
    VIEW DETAILS
Showing 22 to 42 of 149 boats found.
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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 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.