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  • 1973 Gulfstar 41

    1973 Gulfstar 41

    $28,000
    Vandemere, NC
    • Vandemere, NC
    • Sailboat
    • 41' / 0'
    • 1973 / Used
    • $28,000

    Stock #473174 This is a new advertisement, on the market just this week (Nov 14th). Always accepting offers! 1973 Gulfstar 41-ft Center Cockpit Ketch has Encapsulated Keel (no ke... View Details

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    $28,000
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  • Price Drop 1973 Columbia 41

    1973 Columbia 41

    $28,000
    Belvedere Tiburon, CA
    • Belvedere Tiburon, CA
    • Sailboat
    • 41' / 0'
    • 1973 / Used
    • $28,000

    Stock #458807 Video of this vessel available at www [dot] popsells [dot] com/view/458807 This Columbia has now been on the market a couple months. Looking for any offers! A beau... View Details

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    $28,000
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  • 1983 Peterson 42

    1983 Peterson 42

    $28,000
    Ashtabula, OH
    • Ashtabula, OH
    • Sailboat
    • 42' / 0'
    • 1983 / Used
    • $28,000

    Stock #472960 This Peterson has recently been added to market (Nov 12th). Submit your offer today! Professionally maintained custom built 1983 Peterson 42! Rare opportunity to ac... View Details

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    $28,000
    VIEW DETAILS
  • 1983 Sabre 34

    1983 Sabre 34

    $27,950
    Port Orchard, WA
    • Port Orchard, WA
    • Sailboat
    • 34' / 0'
    • 1983 / Used
    • $27,950

    Stock #427931 Video of this vessel available at www [dot] popsells [dot] com/view/427931 Reason for selling is "downsizing (has 3 sailboats)". ANY and ALL offers will be put in... View Details

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    $27,950
    VIEW DETAILS
  • Price Drop 1973 Bristol 40

    1973 Bristol 40

    $27,900
    Jacksonville, FL
    • Jacksonville, FL
    • Sailboat
    • 40' / 0'
    • 1973 / Used
    • $27,900

    Stock #453055 Video of this vessel available at www [dot] popsells [dot] com/view/453055 Reason for selling is "Owner cannot physically handle the boat.". ANY and ALL offers wil... View Details

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    $27,900
    VIEW DETAILS
  • 1987 Catalina 34

    1987 Catalina 34

    $27,000
    Warwick, RI
    • Warwick, RI
    • Sailboat
    • 34' / 0'
    • 1987 / Used
    • $27,000

    Stock #457782 Reason for selling is "Retiring from Boating". ANY and ALL offers will be put in front of our seller! Submit your offer today! Classic Catalina 34! Roomy and comfo... View Details

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    $27,000
    VIEW DETAILS
  • 1940 Australian Square Metre

    1940 Australian Square Metre

    $27,000
    San Diego, CA
    • San Diego, CA
    • Sailboat
    • 40' / 0'
    • 1940 / Used
    • $27,000

    Stock #177855 ANY and ALL offers will be put in front of our seller! Submit your offer today! She has had her hull re-planked with mahogany and the new ribs are laminated with pu... View Details

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    $27,000
    VIEW DETAILS
  • 1985 Sabre 38 MKI

    1985 Sabre 38 MKI

    $26,900
    Middle River, MD
    • Middle River, MD
    • Sailboat
    • 38' / 0'
    • 1985 / Used
    • $26,900

    Stock #301168 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! Excellent Cruiser. M... View Details

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    $26,900
    VIEW DETAILS
  • 1985 O Day 35

    1985 O Day 35

    $25,945
    Bloomington, IN
    • Bloomington, IN
    • Sailboat
    • 35' / 0'
    • 1985 / Used
    • $25,945

    Stock #358323 Video of this vessel available at www [dot] popsells [dot] com/view/358323 Reason for selling is "No longer using". ANY and ALL offers will be put in front of our... View Details

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    $25,945
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  • Price Drop 1978 Herreshoff Meadowlark 37

    1978 Herreshoff Meadowlark 37

    $25,000
    Bradenton, FL
    • Bradenton, FL
    • Sailboat
    • 37' / 0'
    • 1978 / Used
    • $25,000

    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

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    $25,000
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  • 1983 Catalina 38

    1983 Catalina 38

    $25,000
    Dana Point, CA
    • Dana Point, CA
    • Sailboat
    • 38' / 0'
    • 1983 / Used
    • $25,000

    Stock #462265 This Catalina has now been on the market a couple months. Looking for any offers! Priced to sell quickly! Swift sailor, well appointed, roomy interior, bottom paint... View Details

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    $25,000
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  • 1985 Jensen Cal 35 MKII

    1985 Jensen Cal 35 MKII

    $24,995
    Warwick, RI
    • Warwick, RI
    • Sailboat
    • 35' / 0'
    • 1985 / Used
    • $24,995

    Stock #356435 Reason for selling is "Not Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Well equipped classic Cal 35 MKII in very nice c... View Details

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    $24,995
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  • Price Drop 2015 Schock Harbor 20

    2015 Schock Harbor 20

    $24,000
    Coronado, CA
    • Coronado, CA
    • Sailboat
    • 20' / 0'
    • 2015 / Used
    • $24,000

    Stock #416323 Video of this vessel available at www [dot] popsells [dot] com/view/416323 Reason for selling is "No Longer Used". ANY and ALL offers will be put in front of our s... View Details

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    $24,000
    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. Mooring... View Details

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    $23,500
    VIEW DETAILS
  • Price Drop 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

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    $23,000
    VIEW DETAILS
  • Price Drop 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

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    $21,900
    VIEW DETAILS
  • 1983 Hinterhoeller Niagara 35

    1983 Hinterhoeller Niagara 35

    $21,900
    Fort Pierce, FL
    • Fort Pierce, FL
    • Sailboat
    • 35' / 0'
    • 1983 / Used
    • $21,900

    Stock #424922 Video of this vessel available at www [dot] popsells [dot] com/view/424922 Reason for selling is "No longer using". ANY and ALL offers will be put in front of our... View Details

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    $21,900
    VIEW DETAILS
  • Price Drop 1982 Yorktown Center Cockpit

    1982 Yorktown Center Cockpit

    $21,000
    Wilmington, CA
    • Wilmington, CA
    • Sailboat
    • 45' / 0'
    • 1982 / Used
    • $21,000

    Stock #400448 Video of this vessel available at www [dot] popsells [dot] com/view/400448 ANY and ALL offers will be put in front of our seller! Submit your offer today! Recently... View Details

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    $21,000
    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

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    $20,750
    VIEW DETAILS
  • Price Drop 1987 Gulf Coast 32 Pilothouse

    1987 Gulf Coast 32 Pilothouse

    $20,250
    Patrick AFB, FL
    • Patrick AFB, FL
    • Sailboat
    • 32' / 0'
    • 1987 / Used
    • $20,250

    Stock #416650 Video of this vessel available at www [dot] popsells [dot] com/view/416650 ANY and ALL offers will be put in front of our seller! Submit your offer today! Get read... View Details

    View 10 Photos and Details Contact Seller
    $20,250
    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
    VIEW DETAILS
Showing 85 to 105 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.