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  • 1985 C & C Landfall 39

    1985 C & C Landfall 39

    $59,000
    Racine, WI
    • Racine, WI
    • Sailboat
    • 39' / 12'
    • 1985 / Used
    • $59,000

    C&C Landfall 39A proven offshore cruising yacht with a balance of performance and comfort, this C&C Landfall 39 is fully equipped and extensively upgraded. Built by C&C Yachts, she... View Details

    View 57 Photos and Details Contact Seller
    $59,000
    VIEW DETAILS
  • 1978 Westsail 42

    1978 Westsail 42

    $59,000
    Middle River, MD
    • Middle River, MD
    • Sailboat
    • 42' / 0'
    • 1978 / Used
    • $59,000

    Stock #417211 Reason for selling is "Not Using it.". ANY and ALL offers will be put in front of our seller! Submit your offer today! Nice Westsail Cruiser! These boats have sail... View Details

    View 10 Photos and Details Contact Seller
    $59,000
    VIEW DETAILS
  • 1993 Beneteau First 35.5

    1993 Beneteau First 35.5

    $57,900
    Melbourne, FL
    • Melbourne, FL
    • Sailboat
    • 35' / 0'
    • 1993 / Used
    • $57,900

    Stock #454865 Reason for selling is "not using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Elegant And Fast 1993 Beneteau First 35.5 Racer/... View Details

    View 10 Photos and Details Contact Seller
    $57,900
    VIEW DETAILS
  • 1980 Other 30

    1980 Other 30

    $57,500
    Cohasset, MA
    • Cohasset, MA
    • Sailboat
    • 30' / 0'
    • 1980 / Used
    • $57,500

    Stock #299074 ANY and ALL offers will be put in front of our seller! Submit your offer today! Custom Re-Fit! Over 6' Headroom Below! Power Winch! Half-Dodger! Battenless Mainsail... View Details

    View 10 Photos and Details Contact Seller
    $57,500
    VIEW DETAILS
  • 1995 Catalina 36 Mark II Shoal Draft

    1995 Catalina 36 Mark II Shoal Draft

    $56,000
    Fort Myers Beach, FL
    • Fort Myers Beach, FL
    • Sailboat
    • 36' / 0'
    • 1995 / Used
    • $56,000

    Stock #339883 Reason for selling is "Upgrading". ANY and ALL offers will be put in front of our seller! Submit your offer today! Beautiful Catalina MK II Shoal Draft Wing Keel,... View Details

    View 10 Photos and Details Contact Seller
    $56,000
    VIEW DETAILS
  • 1979 Pearson 40

    1979 Pearson 40

    $55,000
    Miami, FL
    • Miami, FL
    • Sailboat
    • 40' / 0'
    • 1979 / Used
    • $55,000

    Stock #306233 Video of this vessel available at www [dot] popsells [dot] com/view/306233 Reason for selling is "Looking to go bigger". ANY and ALL offers will be put in front of... View Details

    View 10 Photos and Details Contact Seller
    $55,000
    VIEW DETAILS
  • 2002 Corsair F-28R

    2002 Corsair F-28R

    $55,000
    San Pedro, CA

    Well equipped and well maintained 2002 Corsair 28R with the sought after Visani configuration! Most notable besides the boat itself is that it comes with a very rare and desirable... View Details

    View 17 Photos and Details Contact Seller
    $55,000
    VIEW DETAILS
  • 1971 Other 37

    1971 Other 37

    $51,700
    Connelly, NY
    • Connelly, NY
    • Sailboat
    • 36' / 0'
    • 1971 / Used
    • $51,700

    Stock #334047 ANY and ALL offers will be put in front of our seller! Submit your offer today! Banjer 37 lots of recent work done, a Classic Ketch with re-powered diesel Hull #51... View Details

    View 10 Photos and Details Contact Seller
    $51,700
    VIEW DETAILS
  • 1996 Hunter 40.5 Legend

    1996 Hunter 40.5 Legend

    $49,900
    Ruskin, FL
    • Ruskin, FL
    • Sailboat
    • 40' / 0'
    • 1996 / Used
    • $49,900

    Stock #451919 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! Newer sails! Generat... View Details

    View 10 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • 1946 Ed Monk Custom 65

    1946 Ed Monk Custom 65

    $49,500
    Brinnon, WA
    • Brinnon, WA
    • Sailboat
    • 65' / 0'
    • 1946 / Used
    • $49,500

    Stock #404692 Reason for selling is "Job Change". ANY and ALL offers will be put in front of our seller! Submit your offer today! 1946 ED MONK!! Must see! Hull restored. Recentl... View Details

    View 10 Photos and Details Contact Seller
    $49,500
    VIEW DETAILS
  • Price Drop 1973 Gulfstar 44

    1973 Gulfstar 44

    $49,000
    Key West, FL
    • Key West, FL
    • Sailboat
    • 44' / 0'
    • 1973 / Used
    • $49,000

    Stock #339042 Video of this vessel available at www [dot] popsells [dot] com/view/339042 Reason for selling is "Change in life priorities". ANY and ALL offers will be put in fro... View Details

    View 10 Photos and Details Contact Seller
    $49,000
    VIEW DETAILS
  • Price Drop 1982 Ta Chiao CT-42 Mermaid

    1982 Ta Chiao CT-42 Mermaid

    $47,500
    Coronado, CA
    • Coronado, CA
    • Sailboat
    • 42' / 0'
    • 1982 / Used
    • $47,500

    Stock #462364 Video of this vessel available at www [dot] popsells [dot] com/view/462364 Reason for selling is "No longer used". This Ta Chiao has now been on the market more th... View Details

    View 10 Photos and Details Contact Seller
    $47,500
    VIEW DETAILS
  • Price Drop 2000 Catalina 36 MKII

    2000 Catalina 36 MKII

    $45,000
    Dunedin, FL
    • Dunedin, FL
    • Sailboat
    • 36' / 0'
    • 2000 / Used
    • $45,000

    Stock #438188 Video of this vessel available at www [dot] popsells [dot] com/view/438188 Reason for selling is "Ready for the happy new owner". ANY and ALL offers will be put in... View Details

    View 11 Photos and Details Contact Seller
    $45,000
    VIEW DETAILS
  • 1986 O Day 40 Deep

    1986 O Day 40 Deep

    $44,500
    Coupeville, WA
    • Coupeville, WA
    • Sailboat
    • 40' / 0'
    • 1986 / Used
    • $44,500

    Stock #469143 Video of this vessel available at www [dot] popsells [dot] com/view/469143 Reason for selling is "Not using that much". This O'day has been on the market for more... View Details

    View 10 Photos and Details Contact Seller
    $44,500
    VIEW DETAILS
  • 1990 Herreshoff 37 Diddikai

    1990 Herreshoff 37 Diddikai

    $44,350
    Marco Island, FL
    • Marco Island, FL
    • Sailboat
    • 37' / 0'
    • 1990 / Used
    • $44,350

    Stock #391951 Video of this vessel available at www [dot] popsells [dot] com/view/391951 Reason for selling is "Moving to Canada". ANY and ALL offers will be put in front of our... View Details

    View 10 Photos and Details Contact Seller
    $44,350
    VIEW DETAILS
  • Price Drop 1974 Gulfstar 41 Ketch

    1974 Gulfstar 41 Ketch

    $41,800
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 41' / 0'
    • 1974 / Used
    • $41,800

    Stock #429648 Video of this vessel available at www [dot] popsells [dot] com/view/429648 Reason for selling is "Done Sailing for Now". ANY and ALL offers will be put in front of... View Details

    View 10 Photos and Details Contact Seller
    $41,800
    VIEW DETAILS
  • 1977 Tartan 42

    1977 Tartan 42

    $41,150
    San Diego, CA
    • San Diego, CA
    • Sailboat
    • 42' / 0'
    • 1977 / Used
    • $41,150

    Stock #448537 Video of this vessel available at www [dot] popsells [dot] com/view/448537 Reason for selling is "No longer used". ANY and ALL offers will be put in front of our s... View Details

    View 11 Photos and Details Contact Seller
    $41,150
    VIEW DETAILS
  • Price Drop 1979 Cape Dory 36

    1979 Cape Dory 36

    $40,000
    League City, TX
    • League City, TX
    • Sailboat
    • 36' / 0'
    • 1979 / Used
    • $40,000

    Stock #422752 Video of this vessel available at www [dot] popsells [dot] com/view/422752 Reason for selling is "Bought new boat". ANY and ALL offers will be put in front of our... View Details

    View 11 Photos and Details Contact Seller
    $40,000
    VIEW DETAILS
  • 1967 Morgan 34

    1967 Morgan 34

    $40,000
    Crystal River, FL
    • Crystal River, FL
    • Sailboat
    • 34' / 0'
    • 1967 / Used
    • $40,000

    Stock #133855 Reason for selling is "No time to use". ANY and ALL offers will be put in front of our seller! Submit your offer today! Popular Morgan 34! 1967 Morgan 34 for sale... View Details

    View 10 Photos and Details Contact Seller
    $40,000
    VIEW DETAILS
  • Price Drop 1981 Ericson 38

    1981 Ericson 38

    $39,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 38' / 0'
    • 1981 / Used
    • $39,900

    Stock #449972 Reason for selling is "No Longer Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Add Bottom Paint and This One Is Ready To... View Details

    View 10 Photos and Details Contact Seller
    $39,900
    VIEW DETAILS
  • Price Drop 2002 Hunter 326 Cruiser

    2002 Hunter 326 Cruiser

    $39,900
    Green Cove Springs, FL
    • Green Cove Springs, FL
    • Sailboat
    • 32' / 0'
    • 2002 / Used
    • $39,900

    Stock #391868 Video of this vessel available at www [dot] popsells [dot] com/view/391868 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
    $39,900
    VIEW DETAILS
Showing 43 to 63 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.