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Boats for sale in Winter Haven Florida

There are 1658 new and used boats for sale in Winter Haven, Florida. Browse Fishing, Center Console, Pontoon, Bowrider, PWC / Waverunner, and Deck Boat from brands like Yamaha, Sea Doo, Bayliner, Hurricane, Key West, and Sea Ray on BoatCrazy. View a wide selection of boats from $2,481 to $1,535,977.
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  • Boats
  • Within 100 Miles Of
    Winter Haven, Florida
1,658 boats found within 100 miles from Winter Haven, Florida
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  • 2006 Marlago FS35 Sport w Cuddy Cabin

    2006 Marlago FS35 Sport w Cuddy Cabin

    $129,000
    Vero Beach, FL

    Stock #365889 Reason for selling is "No Longer Using". ANY and ALL offers will be put in front of our seller! Submit your offer today! Big Center Console with Cuddy and Twin 350... View Details

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    $129,000
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  • 1992 Other Tropic 1200

    1992 Other Tropic 1200

    $65,000
    Placida, FL
    • Placida, FL
    • Sailboat
    • 42'
    • 1992 / Used
    • $65,000

    Stock #438378 Video of this vessel available at www [dot] popsells [dot] com/view/438378 Reason for selling is "No longer using". ANY and ALL offers will be put in front of our... View Details

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    $65,000
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  • 2018 Nautic Star 215 XTS

    2018 Nautic Star 215 XTS

    $39,500
    Ocala, FL

    Stock #465710 Reason for selling is "Not using it enough to justify keeping it". This is a new advertisement, on the market just this week (May 7th). Always accepting offers! We... View Details

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    $39,500
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  • 2013 Sea Hunt Escape 188 LE

    2013 Sea Hunt Escape 188 LE

    $18,000
    Vero Beach, FL
    • Vero Beach, FL
    • Fishing
    • 18'
    • 2013 / Used
    • $18,000

    Stock #365075 Video of this vessel available at www [dot] popsells [dot] com/view/365075 Reason for selling is "new baby coming - no time for boating right now!". ANY and ALL of... View Details

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    $18,000
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  • Price Drop 2003 Pursuit 3070 Offshore CC

    2003 Pursuit 3070 Offshore CC

    $70,000
    Vero Beach, FL

    Stock #466175 Video of this vessel available at www [dot] popsells [dot] com/view/466175 Reason for selling is "Downsizing". ANY and ALL offers will be put in front of our selle... View Details

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    $70,000
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  • Price Drop 2006 Duffy 37 Downeast

    2006 Duffy 37 Downeast

    $399,000
    Fort Pierce, FL
    • Fort Pierce, FL
    • Fishing
    • 37'
    • 2006 / Used
    • $399,000

    2006 Duffy/Campbell Custom Yachts - Atlantic 37Built down lobster boat hull designed by Spencer Lincoln and built with a yacht finish forcoastal cruising and recreational fishing.... View Details

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    $399,000
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  • Price Drop 2003 Hydra Sports 2600WA

    2003 Hydra Sports 2600WA

    $71,600
    Alva, FL

    Stock #474887 Reason for selling is "Has too many boats". ANY and ALL offers will be put in front of our seller! Submit your offer today! NICE FISHING BOAT READY FOR THE WATER!... View Details

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    $71,600
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  • Price Drop 2016 Yamaha 242 Limited S

    2016 Yamaha 242 Limited S

    $42,000
    North Fort Myers, FL
    • North Fort Myers, FL
    • Jet boat
    • 24'
    • 2016 / Used
    • $42,000

    Stock #469288 Reason for selling is "Time for change". ANY and ALL offers will be put in front of our seller! Submit your offer today! 242 Limited S powered by Twin 1.8L High Ou... View Details

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    $42,000
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  • 2003 Formula 260SS

    2003 Formula 260SS

    $30,000
    North Fort Myers, FL
    • North Fort Myers, FL
    • Cuddy Cabin
    • 26'
    • 2003 / Used
    • $30,000

    Stock #476898 This Formula has now been on the market a couple months. Looking for any offers! NICE Cuddy Cabin! Bimini 6.2L V8 Dual prop. Looks great! Timeless 2003 Formula 260... View Details

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    $30,000
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  • 2022 Premier 230 Sunsation

    2022 Premier 230 Sunsation

    $50,000
    Moore Haven, FL
    • Moore Haven, FL
    • Pontoon
    • 23'
    • 2022 / Used
    • $50,000

    Stock #478081 This Premier has now been on the market a couple months. Looking for any offers! Ready for the water. Perfect for summer fun with friends and family. For sale: Pre... View Details

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    $50,000
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  • Price Drop 1994 Pro Line 2950

    1994 Pro Line 2950

    $32,999
    Port Orange, FL
    • Port Orange, FL
    • Walkaround
    • 29'
    • 1994 / Used
    • $32,999

    Stock #462613 Video of this vessel available at www [dot] popsells [dot] com/view/462613 Reason for selling is "Downsizing". ANY and ALL offers will be put in front of our selle... View Details

    View 10 Photos and Details Contact Seller
    $32,999
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  • Price Drop 1999 Sea Ray 290 Sundancer

    1999 Sea Ray 290 Sundancer

    $29,900
    Port Orange, FL

    Stock #481384 Video of this vessel available at www [dot] popsells [dot] com/view/481384 Reason for selling is "Cannot use boat anymore.". This Sea Ray has now been on the marke... View Details

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    $29,900
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  • Price Drop 2026 Stingray 173CC

    2026 Stingray 173CC

    $38,762
    Port Orange, FL

    Ready to make waves? The 173CC is the perfect entry into the boating life, especially for families or groups of up to seven looking for a versatile day on the water. With its sport... View Details

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    $38,762
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  • 2026 Bennington 18 S Fish and Cruise

    2026 Bennington 18 S Fish and Cruise

    $42,793
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 19'
    • 2026 / New
    • $42,793

    If your ideal weekend involves a blend of relaxation and reeling in a big one, look no further. This Bennington S-Series, configured as the ultimate Fish and Cruise machine, is cra... View Details

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    $42,793
    VIEW DETAILS
  • 2026 Bennington 20 S Fishing

    2026 Bennington 20 S Fishing

    $47,510
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 20'
    • 2026 / New
    • $47,510

    If your perfect Saturday involves a dawn patrol for bass and a sunset cruise with the crew, the Bennington 20 S 4 Point Fishing is your new best friend. This vessel is the ultimate... View Details

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    $47,510
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  • 2026 Bennington 21 S Fish and Cruise

    2026 Bennington 21 S Fish and Cruise

    $56,802
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $56,802

    Step aboard the Bennington 21SFCSF, the ultimate party-and-pontoon-fishing hybrid! This is the boat for the family or friend group that can never quite agree on the day's activ... View Details

    View 18 Photos and Details Contact Seller
    $56,802
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  • 2026 Bennington 22 S Stern Radius

    2026 Bennington 22 S Stern Radius

    $59,930
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22'
    • 2026 / New
    • $59,930

    If you're seeking the ultimate on-water escape, look no further than this Bennington beauty. This vessel is perfectly designed for those who love to gather friends and family f... View Details

    View 19 Photos and Details Contact Seller
    $59,930
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  • 2026 Bennington 21 S Cruise

    2026 Bennington 21 S Cruise

    $61,954
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $61,954

    If your ideal weekend involves a seamless blend of adrenaline and pure relaxation, this 21 S Cruise is your match. Dressed to impress in Luminous Blue with sleek Matte Black accent... View Details

    View 21 Photos and Details Contact Seller
    $61,954
    VIEW DETAILS
  • 2026 Starcraft SVX 211 OB

    2026 Starcraft SVX 211 OB

    $62,971
    Port Orange, FL
    • Port Orange, FL
    • Deck Boat
    • 21'
    • 2026 / New
    • $62,971

    This is the kind of boat that turns a “what should we do today?” into an easy decision. Built for families and friend groups who want one platform that can do a little bit of every... View Details

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    $62,971
    VIEW DETAILS
  • 2026 Bennington 21 S SWINGBACK

    2026 Bennington 21 S SWINGBACK

    $69,072
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $69,072

    If you’re the kind of person who believes a Saturday isn't complete without a sun-soaked gathering, the Bennington 21SSB is your new best friend. This pontoon is a social butte... View Details

    View 22 Photos and Details Contact Seller
    $69,072
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  • 2026 Bennington 21 S FISH AND CRUISE

    2026 Bennington 21 S FISH AND CRUISE

    $69,210
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $69,210

    For the angler who refuses to choose between a serious fishing trip and a lively social hour, the Bennington 21SFC is the ultimate multipurpose escape. This isn't just a pontoo... View Details

    View 23 Photos and Details Contact Seller
    $69,210
    VIEW DETAILS
Showing 1534 to 1554 of 1,658 boats found.
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