Boats for sale in Winter Haven Florida - BoatCrazy

1,603 boats found within 100 miles from Winter Haven, Florida

Advertisement

Back

Filter

Price Drop
2026 Bennington 20 S Fishing

$39,971

Port Orange, FL
- Port Orange, FL
- Pontoon
- 20'
- 2026 / New
- $39,971
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

View 23 Photos and Details Contact Seller

$39,971
VIEW DETAILS
Price Drop
2026 Bennington 21 S Fish and Cruise

$54,801

Port Orange, FL
- Port Orange, FL
- Pontoon
- 21'
- 2026 / New
- $54,801
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

$54,801
VIEW DETAILS
Price Drop
2026 Bennington 21 S Cruise

$59,754

Port Orange, FL
- Port Orange, FL
- Pontoon
- 21'
- 2026 / New
- $59,754
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

$59,754
VIEW DETAILS
Advertisement
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

View 23 Photos and Details Contact Seller

$62,971
VIEW DETAILS
Price Drop
2026 Bennington 21 S SWINGBACK

$68,472

Port Orange, FL
- Port Orange, FL
- Pontoon
- 21'
- 2026 / New
- $68,472
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

$68,472
VIEW DETAILS
Price Drop
2026 Bennington 21 S FISH AND CRUISE

$67,973

Port Orange, FL
- Port Orange, FL
- Pontoon
- 21'
- 2026 / New
- $67,973
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

$67,973
VIEW DETAILS
Price Drop
2026 Bennington 22 S Swingback

$69,791

Port Orange, FL
- Port Orange, FL
- Pontoon
- 22'
- 2026 / New
- $69,791
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

View 20 Photos and Details Contact Seller

$69,791
VIEW DETAILS
Advertisement
Advertisement
Price Drop
2026 Bennington 22 S STERN RADIUS

$77,691

Port Orange, FL
- Port Orange, FL
- Pontoon
- 22'
- 2026 / New
- $77,691
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

View 24 Photos and Details Contact Seller

$77,691
VIEW DETAILS
Advertisement
Price Drop
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

View 26 Photos and Details Contact Seller

$121,524
VIEW DETAILS
Price Drop
2026 Tidewater 232 LXF

$117,979

Port Orange, FL
- Port Orange, FL
- Fishing Center Console
- 23'
- 2026 / New
- $117,979
If you're looking for a boat that's ready for adventure, the Tidewater 232 LXF is calling your name! This beauty is perfectly suited for those who love to spend their days... View Details

View 22 Photos and Details Contact Seller

$117,979
VIEW DETAILS
Price Drop
2026 Bennington 26 M STERN LOUNGE

$169,714

Port Orange, FL
- Port Orange, FL
- Pontoon
- 28'
- 2026 / New
- $169,714
Imagine the ultimate social hub that doesn't just sit on the water—it commands it. This Bennington 26 M Stern Lounge is the dream vessel for the consummate host who believes th... View Details

View 24 Photos and Details Contact Seller

$169,714
VIEW DETAILS
Price Drop
2026 World Cat 280 Dual Console

$289,979

Port Orange, FL
- Port Orange, FL
- Catamaran
- 27'
- 2026 / New
- $289,979
Here’s a look at the latest from World Cat, a versatile boat that's ready for any adventure you throw its way. The 280DC offers an aggressive bow design with integrated LED doc... View Details

View 40 Photos and Details Contact Seller

$289,979
VIEW DETAILS
Advertisement
2026 Tidewater 220CC

$87,462

Port Orange, FL
- Port Orange, FL
- Fishing Center Console
- 22'
- 2026 / New
- $87,462
The Tidewater 220 CC is the ultimate "yes" boat for the coastal adventurer who refuses to be pinned down to one activity. Boasting a generous 8' 10" beam, this c... View Details

View 19 Photos and Details Contact Seller

$87,462
VIEW DETAILS
Advertisement
Price Drop
2026 Bennington 20 S CRUISE

$58,971

Port Orange, FL
- Port Orange, FL
- Pontoon
- 20'
- 2026 / New
- $58,971
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

$58,971
VIEW DETAILS
Price Drop
2026 Bennington 22 S 4 PT FISHING

$64,971

Port Orange, FL
- Port Orange, FL
- Pontoon
- 22'
- 2026 / New
- $64,971
The Bennington 22SF is the ultimate "choose your own adventure" vessel, perfectly blurring the lines between a serious angling machine and a high-end entertainment lounge... View Details

View 21 Photos and Details Contact Seller

$64,971
VIEW DETAILS
2026 Tidewater 2110 Bay Max

$72,027

Port Orange, FL
- Port Orange, FL
- Fishing
- 21'
- 2026 / New
- $72,027
View Details

View 19 Photos and Details Contact Seller

$72,027
VIEW DETAILS
2027 Starcraft J7 JET SUPER SPORT

$43,363

Port Orange, FL
- Port Orange, FL
- Pontoon
- 17'
- 2027 / New
- $43,363
Performance Redefined: The Starcraft SV J7 Super SportWhile the standard J7 is a practical workhorse, the Starcraft SV J7 Super Sport is its high-octane, aggressive sibling. Draped... View Details

View 15 Photos and Details Contact Seller

$43,363
VIEW DETAILS
2020 Bossman Xtreme 20

$40,800

Daytona Beach, FL
- Daytona Beach, FL
- Fishing Bay / Flats / Skiff
- 20'
- 2020 / Used
- $40,800
Stock #448557 Video of this vessel available at www [dot] popsells [dot] com/view/448557 Reason for selling is "Not using enough to keep it.". ANY and ALL offers will be put in... View Details

View 10 Photos and Details Contact Seller

$40,800
VIEW DETAILS
Advertisement
2015 Yamaha 242 LIMITED S

$44,350

Daytona Beach, FL
- Daytona Beach, FL
- Jet boat
- 24'
- 2015 / Used
- $44,350
Stock #494098 This is a new advertisement, on the market just this week (Jun 17th). Always accepting offers! VERY NICE BOAT READY FOR THE WATER! 2025 TANDEM AXLE TRAILER INCLUDED... View Details

View 7 Photos and Details Contact Seller

$44,350
VIEW DETAILS
Price Drop
2005 Regal 2450

$20,000

Port Orange, FL
- Port Orange, FL
- Cuddy Cabin
- 24'
- 2005 / Used
- $20,000
Stock #477660 Video of this vessel available at www [dot] popsells [dot] com/view/477660 Reason for selling is "Not using it enough". ANY and ALL offers will be put in front of... View Details

View 10 Photos and Details Contact Seller

$20,000
VIEW DETAILS
Price Drop
2024 Sea Fox 231 Bay Fox

$39,999

Port Orange, FL
- Port Orange, FL
- Fishing Bay / Flats / Skiff
- 22'
- 2024 / Used
- $39,999
Stock #490933 Reason for selling is "Replacing with new". This Sea Fox has been on the market for more than 30 days (May 16th). If you are thinking of making an offer, submit it... View Details

View 10 Photos and Details Contact Seller

$39,999
VIEW DETAILS

Showing 1492 to 1512 of 1,603 boats found.

Prev

...
70
71
72
73
74
...

Next