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  • 1971 Morgan 42-2

    1971 Morgan 42-2

    $19,999
    Honolulu, HI
    • Honolulu, HI
    • Sailboat
    • 42' / 0'
    • 1971 / Used
    • $19,999

    Stock #435692 Reason for selling is "Life Changes". ANY and ALL offers will be put in front of our seller! Submit your offer today! A 1971 Morgan 42-2 Great for Living Aboard an... View Details

    View 4 Photos and Details Contact Seller
    $19,999
    VIEW DETAILS
  • 1987 Ferro 46

    1987 Ferro 46

    $19,950
    Bridgeport, CT
    • Bridgeport, CT
    • Sailboat
    • 46' / 0'
    • 1987 / Used
    • $19,950

    Stock #330926 Reason for selling is "Moving On to Something Else". ANY and ALL offers will be put in front of our seller! Submit your offer today! 1987 William Ferro custom scho... View Details

    View 10 Photos and Details Contact Seller
    $19,950
    VIEW DETAILS
  • Price Drop 1979 CSY 33

    1979 CSY 33

    $19,900
    Montauk, NY
    • Montauk, NY
    • Sailboat
    • 33' / 0'
    • 1979 / Used
    • $19,900

    Stock #326032 Reason for selling is "Not Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! 1979 CSY 33 with updated sails, canvas, and cush... View Details

    View 9 Photos and Details Contact Seller
    $19,900
    VIEW DETAILS
  • 1947 Paul Luke Friendship 32

    1947 Paul Luke Friendship 32

    $19,000
    Ventura, CA
    • Ventura, CA
    • Sailboat
    • 32' / 0'
    • 1947 / Used
    • $19,000

    Stock #234171 Video of this vessel available at www [dot] popsells [dot] com/view/234171 ANY and ALL offers will be put in front of our seller! Submit your offer today! 32 Foot... View Details

    View 10 Photos and Details Contact Seller
    $19,000
    VIEW DETAILS
  • Price Drop 1983 Pearson 303

    1983 Pearson 303

    $19,000
    Rockport, TX
    • Rockport, TX
    • Sailboat
    • 30' / 0'
    • 1983 / Used
    • $19,000

    Stock #459044 Video of this vessel available at www [dot] popsells [dot] com/view/459044 ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautifu... View Details

    View 10 Photos and Details Contact Seller
    $19,000
    VIEW DETAILS
  • 1992 Other 34'6S

    1992 Other 34'6S

    $18,999
    Bristol, RI
    • Bristol, RI
    • Sailboat
    • 34' / 0'
    • 1992 / Used
    • $18,999

    Stock #241572 Reason for selling is "Time has passed and its ready for a new owner". ANY and ALL offers will be put in front of our seller! Submit your offer today! Custom built... View Details

    View 10 Photos and Details Contact Seller
    $18,999
    VIEW DETAILS
  • 1983 Hunter 34

    1983 Hunter 34

    $18,500
    Deale, MD
    • Deale, MD
    • Sailboat
    • 34' / 0'
    • 1983 / Used
    • $18,500

    Stock #432668 ANY and ALL offers will be put in front of our seller! Submit your offer today! 1983 HUNTER 34 CRUISER READY TO SAIL AWAY! You have been asking for this 1983 Hunte... View Details

    View 10 Photos and Details Contact Seller
    $18,500
    VIEW DETAILS
  • 1987 Cheoy Lee 42 Golden Wave

    1987 Cheoy Lee 42 Golden Wave

    $18,000
    Portland, CT
    • Portland, CT
    • Sailboat
    • 42' / 0'
    • 1987 / Used
    • $18,000

    Stock #432139 Video of this vessel available at www [dot] popsells [dot] com/view/432139 Reason for selling is "Lifestyle Change". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $18,000
    VIEW DETAILS
  • 1984 Union 32 EO

    1984 Union 32 EO

    $18,000
    Alameda, CA
    • Alameda, CA
    • Sailboat
    • 32' / 0'
    • 1984 / Used
    • $18,000

    Stock #360093 Video of this vessel available at www [dot] popsells [dot] com/view/360093 ANY and ALL offers will be put in front of our seller! Submit your offer today! 1984 Uni... View Details

    View 10 Photos and Details Contact Seller
    $18,000
    VIEW DETAILS
  • 2015 Coral 16 RIBS

    2015 Coral 16 RIBS

    $17,999
    Miami, FL
    • Miami, FL
    • Sailboat
    • 16' / 0'
    • 2015 / Used
    • $17,999

    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
    $17,999
    VIEW DETAILS
  • 2007 Marlow Hunter 25

    2007 Marlow Hunter 25

    $17,900
    Racine, WI
    • Racine, WI
    • Sailboat
    • 24' / 8'
    • 2007 / Used
    • $17,900

    2007 Hunter 25Year: 2007Builder: Hunter MarineModel: Hunter 25Length Overall: 24'6"Hull Material: FiberglassEngine Type: 2010 Outboard-9.9 TohatsuFuel Type: GasUsage: Overnight-cru... View Details

    View 47 Photos and Details Contact Seller
    $17,900
    VIEW DETAILS
  • Price Drop 1988 Hunter 33.5

    1988 Hunter 33.5

    $17,900
    Laconia, NH
    • Laconia, NH
    • Sailboat
    • 33' / 0'
    • 1988 / Used
    • $17,900

    Stock #448599 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! Clean and Maintained... View Details

    View 10 Photos and Details Contact Seller
    $17,900
    VIEW DETAILS
  • 1991 Hunter Vision 32

    1991 Hunter Vision 32

    $17,900
    Corona, NY
    • Corona, NY
    • Sailboat
    • 32' / 0'
    • 1991 / Used
    • $17,900

    Stock #388920 Video of this vessel available at www [dot] popsells [dot] com/view/388920 Reason for selling is "Sellers are leaving the country". ANY and ALL offers will be put... View Details

    View 10 Photos and Details Contact Seller
    $17,900
    VIEW DETAILS
  • 1980 Catalina 38

    1980 Catalina 38

    $17,750
    Hull, MA
    • Hull, MA
    • Sailboat
    • 38' / 0'
    • 1980 / Used
    • $17,750

    Stock #344687 Reason for selling is "Not using enough". ANY and ALL offers will be put in front of our seller! Submit your offer today! 38' performance cruiser! Fast, seaworthy... View Details

    View 10 Photos and Details Contact Seller
    $17,750
    VIEW DETAILS
  • 1979 S2 Yachts 9.2 C

    1979 S2 Yachts 9.2 C

    $17,700
    New Bern, NC
    • New Bern, NC
    • Sailboat
    • 30' / 0'
    • 1979 / Used
    • $17,700

    Stock #348518 Reason for selling is "Getting out of boating". ANY and ALL offers will be put in front of our seller! Submit your offer today! CENTER COCKPIT, READY TO RIDE THE W... View Details

    View 10 Photos and Details Contact Seller
    $17,700
    VIEW DETAILS
  • 1985 Ericson 32-3

    1985 Ericson 32-3

    $17,500
    Cobb Island, MD
    • Cobb Island, MD
    • Sailboat
    • 32' / 0'
    • 1985 / Used
    • $17,500

    Stock #323583 Reason for selling is "No longer using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Classic sailing yacht! Updated electronics... View Details

    View 11 Photos and Details Contact Seller
    $17,500
    VIEW DETAILS
  • 1984 Island Packet 26 MKII

    1984 Island Packet 26 MKII

    $17,500
    Naples, FL
    • Naples, FL
    • Sailboat
    • 26' / 0'
    • 1984 / Used
    • $17,500

    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
    $17,500
    VIEW DETAILS
  • Price Drop 1972 Grampian 26

    1972 Grampian 26

    $17,500
    Bay City, MI
    • Bay City, MI
    • Sailboat
    • 26' / 0'
    • 1972 / Used
    • $17,500

    Stock #468158 Video of this vessel available at www [dot] popsells [dot] com/view/468158 Reason for selling is "Bought a larger boat". This Grampian has been on the market for m... View Details

    View 10 Photos and Details Contact Seller
    $17,500
    VIEW DETAILS
  • 1987 Catalina 25 POP TOP

    1987 Catalina 25 POP TOP

    $17,500
    Sturgeon Bay, WI
    • Sturgeon Bay, WI
    • Sailboat
    • 25' / 0'
    • 1987 / Used
    • $17,500

    This 1989 Catalina Pop-Top sailboat is an absolute gem—meticulously cared for and in immaculate condition. It comes with a trailer, making transport and storage a breeze. The curre... View Details

    View 30 Photos and Details Contact Seller
    $17,500
    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
  • 1983 Marlow Hunter 27 Cherubini

    1983 Marlow Hunter 27 Cherubini

    $15,500
    Racine, WI
    • Racine, WI
    • Sailboat
    • 27' / 9'
    • 1983 / Used
    • $15,500

    This 1983 Hunter 27 (Tall Rig) has been cared for and loved for many years. The boat has been maintained to a very high level, which will leave a lucky new owner with less headache... View Details

    View 57 Photos and Details Contact Seller
    $15,500
    VIEW DETAILS
Showing 106 to 126 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.