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    Winter Garden, Florida

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Boats for sale in Winter Garden Florida

There are 1295 new and used boats for sale in Winter Garden, Florida. Browse Fishing, Center Console, Pontoon, Outboard Motors, Bowrider, and Bay / Flats / Skiff from brands like Yamaha, Sea Pro, Yamaha Outboards, Key West, Hurricane, and Bayliner on BoatCrazy. View a wide selection of boats from $844 to $799,977.
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  • Boats
  • Within 100 Miles Of
    Winter Garden, Florida
1,295 boats found within 100 miles from Winter Garden, Florida
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  • 2026 Bennington 20 S CRUISE

    2026 Bennington 20 S CRUISE

    $54,900
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 20'
    • 2026 / New
    • $54,900

    Imagine a Saturday where the hardest decision you have to make is whether to lounge on the sunpad or take another lap around the lake. The Bennington 20SL is the ultimate "yes... View Details

    View 19 Photos and Details Contact Seller
    $54,900
    VIEW DETAILS
  • Price Drop 2021 Bayliner T22CC

    2021 Bayliner T22CC

    $46,674
    Port Orange, FL

    The Bayliner Trophy T22CC delivers an ideal balance of fishing capability and family cruising versatility. Powered by an upgraded Mercury 200HP V6 FourStroke engine with only 180 o... View Details

    View 20 Photos and Details Contact Seller
    $46,674
    VIEW DETAILS
  • 2027 World Cat 230DC

    2027 World Cat 230DC

    $180,747
    Port Orange, FL
    • Port Orange, FL
    • Catamaran
    • 22'
    • 2027 / New
    • $180,747

    Imagine the ultimate playground on the water, tailor-made for active families, social weekenders, and die-hard fishing enthusiasts alike. The World Cat 230DC is a multihull marvel... View Details

    View 32 Photos and Details Contact Seller
    $180,747
    VIEW DETAILS
  • 2027 Bennington 18 S CRUISE

    2027 Bennington 18 S CRUISE

    $35,931
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 19'
    • 2027 / New
    • $35,931

    Imagine a sun-drenched Saturday afternoon where the only item on your agenda is choosing which sandbar to drop anchor near. If your idea of the perfect water day involves a close-k... View Details

    View 23 Photos and Details Contact Seller
    $35,931
    VIEW DETAILS
  • 2027 Starcraft J7 Jet Standard

    2027 Starcraft J7 Jet Standard

    $37,876
    Port Orange, FL
    • Port Orange, FL
    • Deck Boat
    • 17'
    • 2027 / New
    • $37,876

    Big Fun, Small Footprint: The Starcraft SV J7In a market obsessed with bigger and pricier, the Starcraft SV J7 makes the opposite case and wins. At just 17 feet, this jet-powered r... View Details

    View 19 Photos and Details Contact Seller
    $37,876
    VIEW DETAILS
  • 2026 Bennington 21 S FISH AND CRUISE

    2026 Bennington 21 S FISH AND CRUISE

    $56,900
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 21'
    • 2026 / New
    • $56,900

    For the "pro-social" angler who refuses to choose between a serious morning catch and a premium afternoon lounge, the Bennington 21SFC is your ultimate dual-threat. This... View Details

    View 19 Photos and Details Contact Seller
    $56,900
    VIEW DETAILS
  • 2027 Bennington 22 S1 STERN RADIUS

    2027 Bennington 22 S1 STERN RADIUS

    $69,872
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22'
    • 2027 / New
    • $69,872

    If your ideal weekend involves sun-drenched cruising, non-stop tunes, and effortless hosting, the Bennington 22 S1 Stern Radius is built for you. This pontoon is designed for the u... View Details

    View 19 Photos and Details Contact Seller
    $69,872
    VIEW DETAILS
  • 2027 Bennington 22 M SWINGBACK

    2027 Bennington 22 M SWINGBACK

    $113,193
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 24'
    • 2027 / New
    • $113,193

    Meet the ultimate vessel for entertainers, sun-seekers, and weekend socialites who treat the water like their personal floating lounge. The Bennington 22MSB is tailor-made for thos... View Details

    View 29 Photos and Details Contact Seller
    $113,193
    VIEW DETAILS
  • 2027 Tidewater 2500 Carolina Bay

    2027 Tidewater 2500 Carolina Bay

    $135,279
    Port Orange, FL

    Whether you are chasing gamefish in shallow back bays, heading out to nearshore reefs, or anchoring at the local sandbar with friends, the Tidewater 2500 Carolina Bay is the ultima... View Details

    View 26 Photos and Details Contact Seller
    $135,279
    VIEW DETAILS
  • 2027 Tidewater 2110 Bay Max

    2027 Tidewater 2110 Bay Max

    $61,451
    Port Orange, FL

    Built for shallow-water anglers and fun-loving weekenders, the Tidewater 2110 Bay Max seamlessly transitions from morning fishing runs to sunny afternoon sandbar hops. With an 8-fo... View Details

    View 12 Photos and Details Contact Seller
    $61,451
    VIEW DETAILS
  • 2027 Starcraft SV 16 OB

    2027 Starcraft SV 16 OB

    $38,717
    Port Orange, FL
    • Port Orange, FL
    • Deck Boat
    • 16'
    • 2027 / New
    • $38,717

    Looking for a deck boat that packs a massive personality into a perfectly sized package? Meet the Starcraft SV 16 OB, a versatile fun-machine built to make the absolute most of eve... View Details

    View 17 Photos and Details Contact Seller
    $38,717
    VIEW DETAILS
  • 2027 World Cat 235TE

    2027 World Cat 235TE

    $189,509
    Port Orange, FL
    • Port Orange, FL
    • Catamaran
    • 22'
    • 2027 / New
    • $189,509

    Designed for die-hard anglers and adventure-loving crews, the World Cat 235TE brings serious excitement to both shallow flats and offshore waters. Drawing a remarkably skinny 9 inc... View Details

    View 23 Photos and Details Contact Seller
    $189,509
    VIEW DETAILS
  • Price Drop 1999 SeaVee 290i

    1999 SeaVee 290i

    $95,000
    Merritt Island, FL

    1999 SeaVee 290iSPECIFICATIONS-Length: 29ft-6in-Beam: 9ft-Deadrise: 25*-Draft: 3.5ft-Power: Cummins diesel 5.9 6bt 270HP-Hours: Approx under 600 hrsALL NEW WITHIN 5 YEARS-New wirin... View Details

    View 29 Photos and Details Contact Seller
    $95,000
    VIEW DETAILS
  • 1997 Other 220 Aquadeck

    1997 Other 220 Aquadeck

    $14,999
    Merritt Island, FL
    • Merritt Island, FL
    • Deck Boat
    • 22'
    • 1997 / Used
    • $14,999

    1997 Citation Sea-pro 220 AquadeckDETAILS AND EQUIPMENT-Completely refurbished -2006 Yamaha V Max 150hp -Brand new Simrad go 9 -Simrad radar-Fusion stereo system 4 speakers -Scan t... View Details

    View 22 Photos and Details Contact Seller
    $14,999
    VIEW DETAILS
  • 2016 Tracker Regency Series 220 DL3

    2016 Tracker Regency Series 220 DL3

    $33,350
    Merritt Island, FL
    • Merritt Island, FL
    • Pontoon
    • 22'
    • 2016 / Used
    • $33,350

    Stock #411919 This Tracker has been on the market for more than 30 days (Aug 17th). If you are thinking of making an offer, submit it today and let's make a deal! CLEAN! NICE TRI... View Details

    View 3 Photos and Details Contact Seller
    $33,350
    VIEW DETAILS
  • 2023 Malibu 23 Lsv Wakesetter

    2023 Malibu 23 Lsv Wakesetter

    $150,000
    Ocala, FL

    Stock #489512 Reason for selling is "Not using it enough to justify keeping it". This Malibu has now been on the market more than a month. Please submit your offer today! 23 Lsv... View Details

    View 10 Photos and Details Contact Seller
    $150,000
    VIEW DETAILS
  • Price Drop 2015 Yamaha 242 Limited S

    2015 Yamaha 242 Limited S

    $39,500
    Daytona Beach, FL
    • Daytona Beach, FL
    • Jet boat
    • 24'
    • 2015 / Used
    • $39,500

    Stock #494098 Video of this vessel available at www [dot] popsells [dot] com/view/494098 Reason for selling is "No longer uses the vessel.". This Yamaha has now been on the mark... View Details

    View 10 Photos and Details Contact Seller
    $39,500
    VIEW DETAILS
  • 2024 Starcraft EX 22 R

    2024 Starcraft EX 22 R

    $23,900
    Port Orange, FL
    • Port Orange, FL
    • Pontoon
    • 22'
    • 2024 / Used
    • $23,900

    Stock #506185 Reason for selling is "Updating Fleet". This Starcraft has recently been added to market (Sep 28th). Submit your offer today! Nice Condition, Great Layout, Service... View Details

    View 10 Photos and Details Contact Seller
    $23,900
    VIEW DETAILS
  • Price Drop 2014 Centurion Enzo SV233

    2014 Centurion Enzo SV233

    $52,500
    Lutz, FL

    Stock #458115 Reason for selling is "No longer use". ANY and ALL offers will be put in front of our seller! Submit your offer today! Well maintained 2014 Centurion Enzo SV233! R... View Details

    View 10 Photos and Details Contact Seller
    $52,500
    VIEW DETAILS
  • Price Drop 2014 Sea Hunt Ultra 235 SE

    2014 Sea Hunt Ultra 235 SE

    $50,000
    Homosassa, FL

    The 2014 Sea Hunt Ultra 235 SE is a 23'6" family friendly center console powered by a 250 hp Yamaha 4-stroke.  Deep-V hull for a dry secure ride. It has 103 gallon gas tank an... View Details

    View 16 Photos and Details Contact Seller
    $50,000
    VIEW DETAILS
  • 2002 Chaparral Signature 260

    2002 Chaparral Signature 260

    $14,500
    Melbourne, FL

    Stock #455465 Video of this vessel available at www [dot] popsells [dot] com/view/455465 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
    $14,500
    VIEW DETAILS
Showing 253 to 273 of 1,295 boats found.
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