Boats for sale in Winter Garden Florida - BoatCrazy

1,464 boats found within 100 miles from Winter Garden, Florida

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2023 Bayliner VR5

$28,855

Tampa, FL
- Tampa, FL
- Bowrider
- 20'
- 2023 / Used
- $28,855
The VR5 builds on Bayliner’s proven V-bottom bowrider heritage, while adding form AND function. Forward, the boat employs Bayliner’s category-leading BeamForward™ design, which car... View Details

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$28,855
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2026 Lund 1600 Fury Tiller

$19,744

Tampa, FL
- Tampa, FL
- Fishing
- 16'
- 2026 / New
- $19,744
a { text-decoration: none; color: #464feb; } tr th, tr td { border: 1px solid #e6e6e6; } tr th { background-color: #f5f5f5; } Turn your next fishing trip into a winning one with th... View Details

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$19,744
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2022 Sailfish 242 CC

$69,697

Tampa, FL
- Tampa, FL
- Fishing Center Console
- 24'
- 2022 / Used
- $69,697
a { text-decoration: none; color: #464feb; } tr th, tr td { border: 1px solid #e6e6e6; } tr th { background-color: #f5f5f5; } Take on offshore fishing or family cruising in the 202... View Details

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$69,697
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2025 Veranda VX27DCRC

$139,975

Tampa, FL
- Tampa, FL
- Pontoon
- 29'
- 2025 / Used
- $139,975
Beautiful 2025 DEMO model Veranda VX27DCRC powered by a Mercury 500 Racing Outboard! Factory Warranty! DEMO MODEL: VX27DCRC Triple Toon 27" High HP Flooring - Woven Pewter Rail Col... View Details

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$139,975
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1987 Fountain 10M Sport

$35,000

Spring Hill, FL
- Spring Hill, FL
- Performance
- 33'
- 1987 / Used
- $35,000
Stock #470503 Reason for selling is "No longer use". ANY and ALL offers will be put in front of our seller! Submit your offer today! 1987 10 Meter Fountain with Tri-Axle Trailer... View Details

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$35,000
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2019 Spyder FX19 Vapor

$43,750

Brooksville, FL
- Brooksville, FL
- Fishing Bay / Flats / Skiff
- 19'
- 2019 / New
- $43,750
This 2019 Spyder FX-19 Is one of the bestselling flats boats on the market. It has been maintained by a seasoned seller, always covered and maintained. Sitting on an aluminum singl... View Details

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$43,750
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1986 Munson 32

$38,000

Lutz, FL
- Lutz, FL
- Pilothouse
- 32'
- 1986 / Used
- $38,000
Stock #373037 ANY and ALL offers will be put in front of our seller! Submit your offer today! Welded Aluminum Vessel Perfect for Dive Charters or Personal Use Around the Islands!... View Details

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$38,000
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2008 Starcraft Aurora Star Step 229 CC

$27,000

Lutz, FL
- Lutz, FL
- Fishing Center Console
- 22'
- 2008 / Used
- $27,000
Stock #463187 Reason for selling is "I'm". ANY and ALL offers will be put in front of our seller! Submit your offer today! Freshly serviced, ready for the water! Low hours! 200... View Details

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$27,000
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2018 Sea Ray SPX 190

$28,000

Lithia, FL
- Lithia, FL
- Deck Boat
- 19'
- 2018 / Used
- $28,000
Stock #383821 Video of this vessel available at www [dot] popsells [dot] com/view/383821 Reason for selling is "Does Not Use Anymore". ANY and ALL offers will be put in front of... View Details

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$28,000
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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

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$32,999
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1999 Sea Ray 290 Sundancer

$27,900

Port Orange, FL
- Port Orange, FL
- Express Cruiser
- 29'
- 1999 / Used
- $27,900
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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$27,900
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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

$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

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$56,802
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2026 Bennington 22 S Stern Radius

$54,979

Port Orange, FL
- Port Orange, FL
- Pontoon
- 22'
- 2026 / New
- $54,979
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

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$54,979
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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

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$61,954
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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
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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

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$69,072
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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

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$69,210
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2026 Bennington 22 S Swingback

$74,452

Port Orange, FL
- Port Orange, FL
- Pontoon
- 22'
- 2026 / New
- $74,452
Step aboard the Bennington 22 S Swingback and you will immediately notice that this is a craft built for the ultimate socialite. If you are the person who loves being the "hos... View Details

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$74,452
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2026 Bennington 22 S STERN RADIUS

$78,692

Port Orange, FL
- Port Orange, FL
- Pontoon
- 22'
- 2026 / New
- $78,692
The Bennington 22SSR is the ultimate companion for the social butterfly who believes the best days are spent surrounded by friends and family. This pontoon is masterfully designed... View Details

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$78,692
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2026 Tidewater 2300 Carolina Bay

$121,524

Port Orange, FL
- Port Orange, FL
- Fishing Bay / Flats / Skiff
- 23'
- 2026 / New
- $121,524
Looking for the ultimate weekend warrior that can handle a fun-filled family day or a serious fishing trip? The Tidewater 2300 CB is your answer. This versatile center console is p... View Details

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$121,524
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Showing 379 to 399 of 1,464 boats found.

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