Boats for sale in Old Town Florida - BoatCrazy

362 boats found within 100 miles out of 14,927 Boats Found

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2026 Stingray 192SC

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Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 20' / 0'
- 2026 / Used
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Get ready to make a splash! The 192SC is the perfect vessel for those who love to enjoy a fun-filled day on the water. With a capacity for up to 10 people, you can bring along all... View Details

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2026 Bennington 20SL

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 20' / 0'
- 2026 / Used
- Call for price
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

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2023 Stingray 211 DC

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Fleming Island, FL
- Fleming Island, FL
- 21' / 0'
- 2023 / Used
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This 2023 Stingray 211DC is a rare find that feels more like a hidden gem than a pre-owned vessel. Having spent its brief 23-hour life tucked away in a covered boat lift with its b... View Details

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2026 Bennington 22SSR

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
- Call for price
For those who dream of sun-drenched days on the water with friends and family, the Bennington 22SSR is your ideal companion. This pontoon is crafted for creating unforgettable mome... View Details

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2026 Stingray 192SC

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Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 20' / 0'
- 2026 / Used
- Call for price
Are you ready for some serious fun on the water? Get ready to explore the exciting features of the 192SC by Stingray Boats! This beauty is perfectly designed for those who love a v... View Details

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2026 Bennington 22SSBSE

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
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If you're looking for a perfect blend of comfort and performance for your days on the water, this Bennington beauty is calling your name. With a spacious deck length of 21′6′ a... View Details

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2026 Barletta A22QC

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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Ready for fun in the sun? The Barletta Aria A22QC is perfect for those who want a blend of comfort, style, and practicality. With its Tempest Gray furniture and Amore Gray flooring... View Details

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2026 Bennington 22SFCSF

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
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Meet the ultimate peacekeeper for your weekend water wars. The Bennington 22 S Fish and Cruise is designed for the family that refuses to pick a lane, effortlessly blending a serio... View Details

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2026 Bennington 21SFSF

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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Cast a line into a world where catching the "big one" doesn't mean sacrificing an ounce of style. This Bennington 21 SF is a masterclass in versatility, blending a se... View Details

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2026 Bennington 22SSSE

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
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Step aboard the Bennington 22 S Stern Fishing boat, an ideal choice for anyone who loves spending time on the water, whether it's for serious angling or just cruising with love... View Details

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2026 Barletta A22UC

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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The Barletta Aria A22UC is a masterclass in the "Intro to Luxury" lifestyle, perfectly blending Barletta’s refined DNA with a layout built for socializing. Designed with... View Details

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2026 Tidewater 198CC

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Fleming Island, FL
- Fleming Island, FL
- Fishing Center Console
- 19' / 0'
- 2026 / Used
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The Tidewater 198 CC is the ultimate "no-compromise" companion for those who want big-boat features in a nimble, manageable package. With its signature Carolina flare and... View Details

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2026 Barletta A22CC

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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For those who love to fish and entertain, the Barletta Aria A22CC is a perfect match. This pontoon boat is designed for casual anglers in the family, offering a fishing center with... View Details

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2026 Bennington 21SSB

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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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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2026 Bennington 21SFC

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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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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2026 Bennington 21SFC

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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For the angler who refuses to choose between a serious day of fishing and a premium lounge experience, the Bennington 21SFC is your ultimate dual-threat. This layout is a dream for... View Details

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2026 Bennington 21SFC

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 21' / 0'
- 2026 / Used
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For the boater who wants to dominate the morning bite and the afternoon sandbar scene, the Bennington 21SFC is a masterclass in versatility. This layout is a dream for the "fi... View Details

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2026 Bennington 22SSB

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
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Imagine a weekend where the only "agenda" is finding the perfect cove and staying there until the stars come out. The Bennington 22SSB is the ultimate vessel for the soci... View Details

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2026 Stingray 212SC

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Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 21' / 0'
- 2026 / Used
- Call for price
Picture this: A perfect day on the water with a group of friends or family, sunshine sparkling on the surface. That's the scene the Stingray 212SC deck boat is made for. This b... View Details

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2026 Bennington 22SSBSF

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
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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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2026 Bennington 22SSB

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Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22' / 0'
- 2026 / Used
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If you are looking to trade the mundane for the shoreline, this Bennington 22SSB is your ultimate ticket to a permanent vacation. This boat is a socialite’s dream, designed specifi... View Details

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Showing 169 to 189 of 362 boats found.

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