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  • 1988 Hunter 333

    1988 Hunter 333

    $15,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 33' / 11'
    • 1988 / Used
    • $15,000

    1988 Hunter Marine 333"AURORA BOREALIS"LOA: 33.33 ftLWL: 26.83 ftBeam: 10.98 ftDraft max: 4.5 ftDisplacement: 10,500lbsSail Area: 522 sq feetBallast: 4000lbsBallast material: LeadK... View Details

    View 17 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • 1987 O Day 322

    1987 O Day 322

    $15,000
    Galveston, TX
    • Galveston, TX
    • Sailboat
    • 32' / 0'
    • 1987 / Used
    • $15,000

    Stock #431683 ANY and ALL offers will be put in front of our seller! Submit your offer today! Excellent condition O'Day 322 sailboat! Recent bottom job. New Lazy Jack sail cover!... View Details

    View 10 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • 1982 Campion C320

    1982 Campion C320

    $15,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 32' / 10'
    • 1982 / Used
    • $15,000

    1982 Campion C-320 Pilot House"LINDISFARNE"LOA: 32ftBeam: 10ft 1inBridge Clearance: 52ftEngine:17hp Volvo Diesel Model: MD7BEngine hours: 804 hrsRadarVHF RadioHood mainsail - fair... View Details

    View 57 Photos and Details Contact Seller
    $15,000
    VIEW DETAILS
  • Price Drop 1973 Grampian G2-34

    1973 Grampian G2-34

    $14,900
    Yorktown, VA
    • Yorktown, VA
    • Sailboat
    • 34' / 0'
    • 1973 / Used
    • $14,900

    Stock #234013 Video of this vessel available at www [dot] popsells [dot] com/view/234013 Reason for selling is "Getting another project boat". ANY and ALL offers will be put in... View Details

    View 10 Photos and Details Contact Seller
    $14,900
    VIEW DETAILS
  • 1972 Westerly 26 Centaur

    1972 Westerly 26 Centaur

    $14,750
    Alderson, WV
    • Alderson, WV
    • Sailboat
    • 26' / 0'
    • 1972 / Used
    • $14,750

    Stock #203644 Reason for selling is "Getting older - Time to let her go and enjoy new hobbies". ANY and ALL offers will be put in front of our seller! Submit your offer today! H... View Details

    View 10 Photos and Details Contact Seller
    $14,750
    VIEW DETAILS
  • 1989 Hunter 30

    1989 Hunter 30

    $14,500
    North East, MD
    • North East, MD
    • Sailboat
    • 30' / 0'
    • 1989 / Used
    • $14,500

    Stock #285844 Reason for selling is "No time to use.". ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautiful classic Sloop Ready for a sailor... View Details

    View 10 Photos and Details Contact Seller
    $14,500
    VIEW DETAILS
  • 1971 Columbia 34 Mark II

    1971 Columbia 34 Mark II

    $13,999
    Stover, MO
    • Stover, MO
    • Sailboat
    • 34' / 0'
    • 1971 / Used
    • $13,999

    Stock #044862 Video of this vessel available at www [dot] popsells [dot] com/view/44862 ANY and ALL offers will be put in front of our seller! Submit your offer today! Summer Sa... View Details

    View 10 Photos and Details Contact Seller
    $13,999
    VIEW DETAILS
  • 1978 Hughes 40

    1978 Hughes 40

    $13,950
    Parlin, NJ
    • Parlin, NJ
    • Sailboat
    • 40' / 0'
    • 1978 / Used
    • $13,950

    Stock #258122 Reason for selling is "Purchased another boat". ANY and ALL offers will be put in front of our seller! Submit your offer today! Spacious, Sporty Center Cockpit Hug... View Details

    View 10 Photos and Details Contact Seller
    $13,950
    VIEW DETAILS
  • 1982 O Day 29

    1982 O Day 29

    $12,800
    Tawas City, MI
    • Tawas City, MI
    • Sailboat
    • 29' / 0'
    • 1982 / Used
    • $12,800

    Stock #248636 Video of this vessel available at www [dot] popsells [dot] com/view/248636 Reason for selling is "Getting out of boating". ANY and ALL offers will be put in front... View Details

    View 10 Photos and Details Contact Seller
    $12,800
    VIEW DETAILS
  • 2010 Macgregor 26M

    2010 Macgregor 26M

    $12,000
    New Rochelle, NY
    • New Rochelle, NY
    • Sailboat
    • 26' / 0'
    • 2010 / Used
    • $12,000

    Stock #342981 Reason for selling is "Upgrading". ANY and ALL offers will be put in front of our seller! Submit your offer today! EASILY TRANSPORTABLE 2010 MACGREGOR 26M MOTOR-SA... View Details

    View 10 Photos and Details Contact Seller
    $12,000
    VIEW DETAILS
  • 1973 Ranger 37 Sloop

    1973 Ranger 37 Sloop

    $12,000
    Honolulu, HI
    • Honolulu, HI
    • Sailboat
    • 37' / 0'
    • 1973 / Used
    • $12,000

    Stock #387501 Reason for selling is "Not Using Enough". ANY and ALL offers will be put in front of our seller! Submit your offer today! Transpac international offshore race winn... View Details

    View 10 Photos and Details Contact Seller
    $12,000
    VIEW DETAILS
  • Price Drop 1983 O Day 28

    1983 O Day 28

    $11,995
    Venice, FL
    • Venice, FL
    • Sailboat
    • 28' / 0'
    • 1983 / Used
    • $11,995

    Stock #417741 Video of this vessel available at www [dot] popsells [dot] com/view/417741 Reason for selling is "Upsizing". ANY and ALL offers will be put in front of our seller!... View Details

    View 10 Photos and Details Contact Seller
    $11,995
    VIEW DETAILS
  • 1980 Balboa 27

    1980 Balboa 27

    $11,750
    Frenchville, PA
    • Frenchville, PA
    • Sailboat
    • 27' / 0'
    • 1980 / Used
    • $11,750

    Stock #243728 Reason for selling is "Not Using/No time because of work.". ANY and ALL offers will be put in front of our seller! Submit your offer today! Trailerable Cruiser. Hi... View Details

    View 10 Photos and Details Contact Seller
    $11,750
    VIEW DETAILS
  • 1984 Other 28

    1984 Other 28

    $10,200
    Forked River, NJ
    • Forked River, NJ
    • Sailboat
    • 28' / 10'
    • 1984 / Used
    • $10,200

    Sailboat - Forked River, NJ 1984 O'Day 28  The boat is in excellent condition and is currently out of the water in Forked River, NJ.   It has mainsail and nearly n... View Details

    View 18 Photos and Details Contact Seller
    $10,200
    VIEW DETAILS
  • Price Drop 1999 Precision 28

    1999 Precision 28

    $10,000
    Holiday, FL
    • Holiday, FL
    • Sailboat
    • 28' / 0'
    • 1999 / Used
    • $10,000

    Stock #387384 Reason for selling is "Not using enough". ANY and ALL offers will be put in front of our seller! Submit your offer today! Clean and well-equipped! Easy to Sail! Ya... View Details

    View 10 Photos and Details Contact Seller
    $10,000
    VIEW DETAILS
  • 1983 Hunter 31

    1983 Hunter 31

    $9,950
    Mystic, CT
    • Mystic, CT
    • Sailboat
    • 31' / 0'
    • 1983 / Used
    • $9,950

    Stock #329591 Reason for selling is "Switching to Power". ANY and ALL offers will be put in front of our seller! Submit your offer today! 31' sloop with racy features, more cont... View Details

    View 10 Photos and Details Contact Seller
    $9,950
    VIEW DETAILS
  • 1982 Catalina 27 Shoal

    1982 Catalina 27 Shoal

    $9,500
    Sausalito, CA
    • Sausalito, CA
    • Sailboat
    • 27' / 0'
    • 1982 / Used
    • $9,500

    Stock #371485 Video of this vessel available at www [dot] popsells [dot] com/view/371485 ANY and ALL offers will be put in front of our seller! Submit your offer today! Well mai... View Details

    View 10 Photos and Details Contact Seller
    $9,500
    VIEW DETAILS
  • Price Drop 1986 Aloha 8.5

    1986 Aloha 8.5

    $8,500
    Warwick, RI
    • Warwick, RI
    • Sailboat
    • 28' / 0'
    • 1986 / Used
    • $8,500

    Stock #446479 Video of this vessel available at www [dot] popsells [dot] com/view/446479 Reason for selling is "Moving Up". ANY and ALL offers will be put in front of our seller... View Details

    View 10 Photos and Details Contact Seller
    $8,500
    VIEW DETAILS
  • 1978 American Spirit 23

    1978 American Spirit 23

    $6,400
    Reedsburg, WI
    • Reedsburg, WI
    • Sailboat
    • 23' / 0'
    • 1978 / Used
    • $6,400

    Stock #298982 Video of this vessel available at www [dot] popsells [dot] com/view/298982 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
    $6,400
    VIEW DETAILS
  • Price Drop 1977 C & C 26

    1977 C & C 26

    $2,500
    Hampton, VA
    • Hampton, VA
    • Sailboat
    • 26' / 10'
    • 1977 / Used
    • $2,500

    The C & C 26 is fixed fin keel, Masthead Sloop rig, with internally-mounted spade type rudder. This boat was hauled out in November 2023. We have two sails Jib and Genoa. View Details

    View 13 Photos and Details Contact Seller
    $2,500
    VIEW DETAILS
  • Price Drop 1981 Hobie Cat 14 Sport/ Beach Cat-NO TRAILER

    1981 Hobie Cat 14 Sport/ Beach Cat-NO TRAILER

    $300
    Morehead City, NC
    • Morehead City, NC
    • Sailboat
    • 14' / 0'
    • 1981 / Used
    • $300

    1981 Hobie Cat 14 left tramp frame needs work with sail View Details

    View 8 Photos and Details Contact Seller
    $300
    VIEW DETAILS
Showing 127 to 147 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.