Boats for sale in Winter Haven Florida

1,533 boats found within 100 miles from Winter Haven, Florida

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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

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$56,900
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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

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$69,872
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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

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$113,193
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2027 Tidewater 2500 Carolina Bay

$135,279

Port Orange, FL
- Port Orange, FL
- Fishing Bay / Flats / Skiff
- 25'
- 2027 / New
- $135,279
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

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$135,279
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2027 Tidewater 2110 Bay Max

$61,451

Port Orange, FL
- Port Orange, FL
- Fishing Bay / Flats / Skiff
- 21'
- 2027 / New
- $61,451
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

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$61,451
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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

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$38,717
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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

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$189,509
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2027 Tidewater 232LXF

$120,090

Port Orange, FL
- Port Orange, FL
- Fishing Center Console
- 23'
- 2027 / New
- $120,090
Designed for adventure-seeking families and coastal anglers who demand equal parts performance and luxury, the Tidewater 232 LXF thrives as an all-in-one day cruiser. Built with a... View Details

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$120,090
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2021 Sea Ray SPX 190

$21,499

Cape Coral, FL
- Cape Coral, FL
- Bowrider
- 19'
- 2021 / Used
- $21,499
Stock #504658 Reason for selling is "Updating Fleet". This Sea Ray has recently been added to market (Sep 16th). Submit your offer today! A Cozy 21' Bow Rider, with a Mercury 15... View Details

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$21,499
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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.". ANY and ALL offers will be put in fr... View Details

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$39,500
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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 been on the market for more than 30 days (Sep 28th). If you are thinking of making an offer, submit it to... View Details

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$23,900
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2021 Hurricane 235 SD

$57,500

North Fort Myers, FL
- North Fort Myers, FL
- Deck Boat
- 23'
- 2021 / Used
- $57,500
Stock #389147 Video of this vessel available at www [dot] popsells [dot] com/view/389147 Reason for selling is "Selling their home, do not need a boat". ANY and ALL offers will... View Details

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$57,500
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1998 Catamaran Cruisers Aqua 62

$110,000

North Fort Myers, FL
- North Fort Myers, FL
- Houseboat
- 62'
- 1998 / Used
- $110,000
Stock #429702 Video of this vessel available at www [dot] popsells [dot] com/view/429702 Reason for selling is "After 15 years they want to travel in thieir motor home". ANY and... View Details

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$110,000
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1992 Mako 210

$13,800

Fort Myers, FL
- Fort Myers, FL
- Walkaround
- 21'
- 1992 / Used
- $13,800
Stock #346553 Reason for selling is "Not Using, Downsizing Boats". ANY and ALL offers will be put in front of our seller! Submit your offer today! Great condition 210! Loaded wi... View Details

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$13,800
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2020 Yellowfin 39 Offshore

$450,000

Fort Myers, FL
- Fort Myers, FL
- Fishing Center Console
- 39'
- 2020 / Used
- $450,000
2020 Yellowfin 39 OffshoreQuad Mercury 350HP Four Strokes Only 700 HoursHull Side Color Black Hull Bottom Color Black Rub Rail Color BlackCONSOLE 39 Console Solid Windshield 2 Cup... View Details

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$450,000
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2019 Robalo R-180 CC

$37,000

Dunnellon, FL
- Dunnellon, FL
- Fishing Center Console
- 18'
- 2019 / Used
- $37,000
Stock #506201 Reason for selling is "Not using it enough to justify keeping it". This Robalo has recently been added to market (Sep 16th). Submit your offer today! Excellent Con... View Details

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$37,000
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2021 Cobalt A29

$150,000

Daytona Beach, FL
- Daytona Beach, FL
- Bowrider
- 29'
- 2021 / Used
- $150,000
Stock #443773 Video of this vessel available at www [dot] popsells [dot] com/view/443773 Reason for selling is "Not using". ANY and ALL offers will be put in front of our seller... View Details

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$150,000
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2026 Barletta Sanza S22QC

$49,987

Daytona Beach, FL
- Daytona Beach, FL
- Pontoon
- 21'
- 2026 / New
- $49,987
The Barletta Sanza S22QC is a masterclass in versatile fun, designed for the social butterfly who believes the best days are spent surrounded by friends, family, and perhaps a furr... View Details

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$49,987
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2026 Barletta Corsa X23U

$109,674

Daytona Beach, FL
- Daytona Beach, FL
- Pontoon
- 23'
- 2026 / New
- $109,674
This Barletta Corsa 23U is a sporty chariot built for those who love to gather and play, but demand a ride that feels solid and luxurious. If your idea of a perfect day includes a... View Details

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$109,674
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2026 Barletta Sanza 20L

$39,989

Daytona Beach, FL
- Daytona Beach, FL
- Pontoon
- 21'
- 2026 / New
- $39,989
The Sanza S20L is the ultimate "welcome to the water" invitation for families and pet lovers who value simplicity without skimping on quality. Designed as a streamlined c... View Details

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$39,989
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2026 Tidewater 256CC

$149,987

Daytona Beach, FL
- Daytona Beach, FL
- Fishing Center Console
- 25'
- 2026 / New
- $149,987
The Tidewater 256 CC is a masterclass in versatility, making it the ultimate match for the active family that refuses to choose between a serious fishing expedition and a sun-soake... View Details

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$149,987
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