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Sailboat boats for sale

There are 152 new and used Sailboat boats for sale. Explore Sailboat brands like Hunter, Catalina, Beneteau, Other, O Day, and Morgan on BoatCrazy. View a wide selection of Sailboat boats from $300 to $695,000.
152 out of 14,966 Boats Found
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  • 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
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  • Price Drop 1979 O Day 37 Mid-Cockpit

    1979 O Day 37 Mid-Cockpit

    $21,500
    Key Largo, FL
    • Key Largo, FL
    • Sailboat
    • 37' / 0'
    • 1979 / Used
    • $21,500

    Stock #448042 Reason for selling is "Upgrading to a Catamaran". ANY and ALL offers will be put in front of our seller! Submit your offer today! Fully off grid, complete solar sy... View Details

    View 10 Photos and Details Contact Seller
    $21,500
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  • Price Drop 2021 Flying Scot 19

    2021 Flying Scot 19

    $20,000
    Sarasota, FL
    • Sarasota, FL
    • Sailboat
    • 19' / 0'
    • 2021 / Used
    • $20,000

    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
    $20,000
    VIEW DETAILS
  • 1980 Hinterhoeller Niagara 35

    1980 Hinterhoeller Niagara 35

    $20,000
    West Haverstraw, NY
    • West Haverstraw, NY
    • Sailboat
    • 35' / 11'
    • 1980 / Used
    • $20,000

    1980 Niagara 35 Classic  designed by mark Ellis, enjoyed a production run thay spanned three decades (1978 to 1995)., live-aboard cruiser with numerus long voyages to the desi... View Details

    View 22 Photos and Details Contact Seller
    $20,000
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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
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  • 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
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  • 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

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    $19,000
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  • 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

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    $18,999
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  • 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

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    $18,500
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  • 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
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  • 1986 Bayfield 29

    1986 Bayfield 29

    $18,000
    Tavernier, FL
    • Tavernier, FL
    • Sailboat
    • 29' / 0'
    • 1986 / Used
    • $18,000

    Stock #479880 This is a new advertisement, on the market just this week (Mar 9th). Always accepting offers! 1986 Bayfield 29. Blue Water Cruiser. Ready for the Next Adventure. I... View Details

    View 3 Photos and Details Contact Seller
    $18,000
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  • 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
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  • 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
  • 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
  • Price Drop 1988 Hunter 33.5

    1988 Hunter 33.5

    $15,900
    Laconia, NH
    • Laconia, NH
    • Sailboat
    • 33' / 0'
    • 1988 / Used
    • $15,900

    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
    $15,900
    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
  • 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
  • 2025 Hobie 16

    2025 Hobie 16

    $15,500
    Coopersville, MI
    • Coopersville, MI
    • Sailboat
    • 16' / 0'
    • 2025 / New
    • $15,500

    The Hobie 16 revolutionized multihull sailing. The Hobie 16 was unleashed on the Southern California beach scene in 1970 and sailing was instantly transformed.The beach-launched Ho... View Details

    View 1 Photo and Details Contact Seller
    $15,500
    VIEW DETAILS
Showing 106 to 126 of 152 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 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.