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  • 1976 Custom Built Finnsailer 29

    1976 Custom Built Finnsailer 29

    $25,250
    Pensacola, FL
    • Pensacola, FL
    • Sailboat
    • 29' / 0'
    • 1976 / Used
    • $25,250

    - Stock #225879 - 1976 FINNSAILER 29 MOTORSAILER BUILT IN FINLAND W/DIESEL YANMAR DIESEL SUPER SPACIOUS AS A LIVEABOARD OR DAYSAILER If you are in the market for a motorsailer,... View Details

    View 10 Photos and Details Contact Seller
    $25,250
    VIEW DETAILS
  • 1979 Sandpiper 32

    1979 Sandpiper 32

    $25,000
    Saint Petersburg, FL
    • Saint Petersburg, FL
    • Sailboat
    • 32' / 0'
    • 1979 / Used
    • $25,000

    - Stock #233274 - This fine vessel won Every race it entered at the St Pete Yacht Club! Decked out, Great Condition, NEW $14k Yanmar motor, This baby is FAST & FINE! If you are... View Details

    View 1 Photo and Details Contact Seller
    $25,000
    VIEW DETAILS
  • 1956 Kettenburg K38

    1956 Kettenburg K38

    $25,000
    Vallejo, CA
    • Vallejo, CA
    • Sailboat
    • 38' / 0'
    • 1956 / Used
    • $25,000

    - Stock #042148 - Classic San Diego Built Kettenburg known as "Aristocrats of sail" If you are in the market for a sloop, look no further than this 1956 Kettenburg K38, just re... View Details

    View 10 Photos and Details Contact Seller
    $25,000
    VIEW DETAILS
  • 1986 Pearson 36-2

    1986 Pearson 36-2

    $25,000
    Harrison Township, MI
    • Harrison Township, MI
    • Sailboat
    • 36' / 0'
    • 1986 / Used
    • $25,000

    - Stock #190154 - A nice sailboat harken roller furling,Mack sail pack to handle the main sail,chart plotter,Alpha 3000 Autopilot If you are in the market for a cruiser, look n... View Details

    View 10 Photos and Details Contact Seller
    $25,000
    VIEW DETAILS
  • 1982 C & C 34

    1982 C & C 34

    $25,000
    Key Largo, FL
    • Key Largo, FL
    • Sailboat
    • 34' / 0'
    • 1982 / Used
    • $25,000

    - Stock #171812 - Great for sailing Bayside or Outside. Completely refitted in spring, 2018. If you are in the market for a sloop, look no further than this 1982 C & C 34, just... View Details

    View 10 Photos and Details Contact Seller
    $25,000
    VIEW DETAILS
  • 1981 Freedom Yachts Cat-Ketch 33

    1981 Freedom Yachts Cat-Ketch 33

    $25,000
    Seward, AK
    • Seward, AK
    • Sailboat
    • 33' / 0'
    • 1981 / Used
    • $25,000

    - Stock #189982 - Current owner since 1997. Two heaters, tender and motor, five sails, bow thruster! If you are in the market for a ketch, look no further than this 1981 Freedo... View Details

    View 10 Photos and Details Contact Seller
    $25,000
    VIEW DETAILS
  • 1977 Golden Hind 31

    1977 Golden Hind 31

    $24,900
    Rye, NH
    • Rye, NH
    • Sailboat
    • 31' / 0'
    • 1977 / Used
    • $24,900

    - Stock #186014 - ONE OF A KIND! Classic British Blue Water Cruiser. If you are in the market for a cutter, look no further than this 1977 Golden Hind 31, just reduced to $24,9... View Details

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    $24,900
    VIEW DETAILS
  • 1976 Irwin 37-3

    1976 Irwin 37-3

    $24,900
    Merritt, NC
    • Merritt, NC
    • Sailboat
    • 37' / 0'
    • 1976 / Used
    • $24,900

    - Stock #223696 - Well Kept Irwin 37 Center Cockpit, Ready to Cruise! If you are in the market for a cutter, look no further than this 1976 Irwin 37-3, priced right at $24,900... View Details

    View 10 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 1988 Catalina 30

    1988 Catalina 30

    $24,900
    Hudson, FL
    • Hudson, FL
    • Sailboat
    • 30' / 10'
    • 1988 / Used
    • $24,900

    The 1988 Catalina 30 is a classic cruising sailboat that has long been appreciated for its combination of performance, comfort, and affordability. With a length overall (LOA) of 30... View Details

    View 24 Photos and Details Contact Seller
    $24,900
    VIEW DETAILS
  • 1989 Hunter 33.5

    1989 Hunter 33.5

    $24,800
    Grand Prairie, TX
    • Grand Prairie, TX
    • Sailboat
    • 33' / 0'
    • 1989 / Used
    • $24,800

    - Stock #154341 - 1989 Hunter Sloop - Ready to be Sold and Set Sail! If you are in the market for a sloop, look no further than this 1989 Hunter 33.5, just reduced to $24,800 (... View Details

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    $24,800
    VIEW DETAILS
  • 1968 CAL 34

    1968 CAL 34

    $24,750
    Portland, OR
    • Portland, OR
    • Sailboat
    • 34' / 0'
    • 1968 / Used
    • $24,750

    - Stock #215723 - Great condition Cal! New engine and a long list of new upgrades! Ready for an extended stay or a nice cruise! If you are in the market for a sloop, look no fu... View Details

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    $24,750
    VIEW DETAILS
  • 1978 Hunter 33

    1978 Hunter 33

    $24,750
    Brookings, OR
    • Brookings, OR
    • Sailboat
    • 33' / 0'
    • 1978 / Used
    • $24,750

    - Stock #223713 - Updated in 2019/2020. Ready for the next adventure. If you are in the market for a cruiser, look no further than this 1978 Hunter 33, priced right at $24,750... View Details

    View 10 Photos and Details Contact Seller
    $24,750
    VIEW DETAILS
  • 1997 Catalina 250

    1997 Catalina 250

    $24,750
    Marina del Rey, CA
    • Marina del Rey, CA
    • Sailboat
    • 25' / 0'
    • 1997 / Used
    • $24,750

    - Stock #231035 - Catalina 250 Sailboat, Yamaha single outboard engine! Ready to sail away! If you are in the market for a sloop, look no further than this 1997 Catalina 250, p... View Details

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    $24,750
    VIEW DETAILS
  • 1984 Pearson 33

    1984 Pearson 33

    $24,750
    Jacksonville, FL
    • Jacksonville, FL
    • Sailboat
    • 33' / 0'
    • 1984 / Used
    • $24,750

    - Stock #219902 - Great condition, turn key, Large salon with expanding table. One head with sink and shower. Navigation station and more! If you are in the market for a sloop,... View Details

    View 10 Photos and Details Contact Seller
    $24,750
    VIEW DETAILS
  • 1986 Hunter 31

    1986 Hunter 31

    $24,500
    Saint Clair Shores, MI
    • Saint Clair Shores, MI
    • Sailboat
    • 31' / 0'
    • 1986 / Used
    • $24,500

    - Stock #031584 - Fresh Water Hunter!! Ready to Set Sail! If you are in the market for a sloop, look no further than this 1986 Hunter 31, just reduced to $24,500 (offers encour... View Details

    View 10 Photos and Details Contact Seller
    $24,500
    VIEW DETAILS
  • 1992 Hunter 27

    1992 Hunter 27

    $24,500
    Excelsior, MN
    • Excelsior, MN
    • Sailboat
    • 27' / 9'
    • 1992 / Used
    • $24,500

    Boat is located in Shorewood, Minnesota. Hunter 27 with significant restoration/service work bringing this boat to excellent condition. Too much new to list. See photos... View Details

    View 12 Photos and Details Contact Seller
    $24,500
    VIEW DETAILS
  • 1974 Ta Chiao CT 41

    1974 Ta Chiao CT 41

    $24,000
    Portland, OR
    • Portland, OR
    • Sailboat
    • 41' / 13'
    • 1974 / Used
    • $24,000

    The boat is in very good condition it has always been stored in the garage.Only asking what I owe, moving and can not take it with me. Lowrance fish finder and marine radio come wi... View Details

    View 2 Photos and Details Contact Seller
    $24,000
    VIEW DETAILS
  • 1982 Catalina 38

    1982 Catalina 38

    $23,900
    Berkeley, CA
    • Berkeley, CA
    • Sailboat
    • 38' / 0'
    • 1982 / Used
    • $23,900

    - Stock #181284 - Catalina 38 racer/cruiser. Sleeps 6, excellent condition, TV/DVD, stereo w/inside-outside speakers. If you are in the market for a sloop, look no further than... View Details

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    $23,900
    VIEW DETAILS
  • 1987 Hunter 37 Legend

    1987 Hunter 37 Legend

    $23,900
    Lake Arthur, LA
    • Lake Arthur, LA
    • Sailboat
    • 37' / 0'
    • 1987 / Used
    • $23,900

    - Stock #197246 - 1987 sailboat made by Hunter , 37 feet long with a Yanmar engine. Great boat! Come check it out! If you are in the market for a cruiser, look no further than... View Details

    View 10 Photos and Details Contact Seller
    $23,900
    VIEW DETAILS
  • 1981 C & C 32

    1981 C & C 32

    $23,750
    South Amboy, NJ
    • South Amboy, NJ
    • Sailboat
    • 32' / 0'
    • 1981 / Used
    • $23,750

    - Stock #196286 - Solo rigged with self-tailing winches! Complete refit 2015-2017 including new main, Genoa, dodger, bimini & much more! If you are in the market for a sloop, l... View Details

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    $23,750
    VIEW DETAILS
  • 1982 O Day 37

    1982 O Day 37

    $23,500
    Patchogue, NY
    • Patchogue, NY
    • Sailboat
    • 37' / 0'
    • 1982 / Used
    • $23,500

    - Stock #196268 - Great classic 37' Center console BLUE WATER boat ready to sail If you are in the market for a sloop, look no further than this 1982 O'day 37, just reduced to... View Details

    View 10 Photos and Details Contact Seller
    $23,500
    VIEW DETAILS
Showing 253 to 273 of 449 boats found.
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Sailboat Boats On Boatcrazy

Sailboats harness wind power for propulsion, offering an eco-friendly and serene boating experience. They come in various types, including sloops, ketches, and catamarans, each with distinct sail configurations. Sizes range from small dinghies to large yachts equipped for ocean crossings. Sailboats are popular for recreational cruising, racing, and liveaboard lifestyles. They require knowledge of wind patterns, navigation, and sail handling, providing an engaging experience for enthusiasts.

Sailboat boats for sale by State