Boats for sale in Leesburg Florida - BoatCrazy

1,194 boats found within 100 miles from Leesburg, Florida

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2027 Bennington 22 S1 STERN RADIUS

$69,872

Fleming Island, FL
- Fleming Island, 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 Stingray 20 SBX

$69,963

Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 20'
- 2027 / New
- $69,963
Designed for thrill-seeking families, sun-chaser crews, and watersports enthusiasts, the Stingray 20 SBX (Sand Bar Extreme) is the ultimate ticket to effortless weekend fun. Built... View Details

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$69,963
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2027 Stingray 20 SBX

$70,462

Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 20'
- 2027 / New
- $70,462
For weekend adventurers and sandbar socialites, the Stingray 20 SBX is built to turn every sunny day into an unforgettable party on the water. With room for up to ten people, this... View Details

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$70,462
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2027 Stingray 211DC

$73,252

Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 21'
- 2027 / New
- $73,252
The Stingray 211DC is the ultimate dream machine for families, water sport lovers, and weekend explorers who want to bring their whole crew along for the ride. Designed with an exp... View Details

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$73,252
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2027 Bennington 22 S1 STERN RADIUS

$73,344

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22'
- 2027 / New
- $73,344
If your dream day on the water involves hosting a lively crew, carving up wake, and soaking in non-stop sunshine, this pontoon is tailored just for you. Built for social butterflie... View Details

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$73,344
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2027 Stingray 231DC

$89,416

Fleming Island, FL
- Fleming Island, FL
- Deck Boat
- 23'
- 2027 / New
- $89,416
Designed for social sun-seekers, active families, and water lovers who refuse to compromise on fun, the Stingray 231DC dual console is the ultimate all-in-one dayboat. With room fo... View Details

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$89,416
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2026 Tidewater 220LXF

$89,987

Fleming Island, FL
- Fleming Island, FL
- Fishing Center Console
- 22'
- 2026 / New
- $89,987
The Tidewater 220 LXF is the ultimate chameleon of the coastline, designed for those who refuse to choose between a serious fishing expedition and a luxurious family sunset cruise.... View Details

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$89,987
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2027 Bennington 22 M SWINGBACK

$113,193

Fleming Island, FL
- Fleming Island, 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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2026 Tidewater 232CC

$114,987

Fleming Island, FL
- Fleming Island, FL
- Fishing Center Console
- 23'
- 2026 / New
- $114,987
Imagine hitting the open water in a vessel designed for pure exhilaration and endless fun. The Tidewater 232 CC is your ticket to adventure, perfectly suited for the angler who lov... View Details

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$114,987
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2025 Sea Hunt Ultra 255SE

$119,987

Fleming Island, FL
- Fleming Island, FL
- Fishing Center Console
- 25'
- 2025 / Used
- $119,987
The flagship of Sea Hunt's Ultra family was built on a simple idea: the boat that catches fish on Saturday should spoil the family on Sunday. The Ultra 255 SE nails both jobs.... View Details

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$119,987
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2027 Tidewater 272CC

$190,343

Fleming Island, FL
- Fleming Island, FL
- Fishing Center Console
- 27'
- 2027 / New
- $190,343
Designed for weekend thrill-seekers, coastal anglers, and social cruisers alike, the Tidewater 272 CC is built to turn every outing into an unforgettable party on the water. Powere... View Details

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$190,343
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2027 Tidewater 3100 Carolina Bay

$375,576

Fleming Island, FL
- Fleming Island, FL
- Fishing Bay / Flats / Skiff
- 31'
- 2027 / New
- $375,576
Ready for the ultimate high-energy weekend on the water? The Tidewater 3100 Carolina Bay is the dream rig for passionate anglers and sun-seeking adventurers who refuse to choose be... View Details

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$375,576
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2027 Bennington 22 S1 FISH AND CRUISE

$66,971

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22'
- 2027 / New
- $66,971
Imagine one pontoon that effortlessly shifts from an early-morning angler’s dream to an afternoon social cruiser. The Bennington 22S1 Fish and Cruise is crafted specifically for mu... View Details

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$66,971
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2027 Bennington 20 S1 STERN RADIUS

$54,671

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 20'
- 2027 / New
- $54,671
If your ideal weekend involves sunny lake cruises, sandbar hangouts, and nonstop watersports, the Bennington 20 S Stern Radius is tailor-made for you. Built for active families, th... View Details

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$54,671
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2027 Bennington 20 S1 STERN RADIUS

$48,254

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 20'
- 2027 / New
- $48,254
If your ideal weekend involves sunny sandbars, endless playlists, and kicked-back relaxation, the Bennington 20 S Stern Radius is tailor-made for you. Built for social weekenders,... View Details

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$48,254
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2027 Bennington 20 S1 4 PT FISHING

$49,905

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 20'
- 2027 / New
- $49,905
Anglers who refuse to choose between serious fishing utility and supreme weekend relaxation will find their perfect match in the Bennington 20 S1 4 Point Fishing pontoon. Powered b... View Details

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$49,905
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2027 Bennington 20 S1 STERN RADIUS

$56,579

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 20'
- 2027 / New
- $56,579
Looking for the ultimate floating lounge that turns every weekend into a high-vibe sandbar party? The Bennington 20 S Stern Radius is custom-made for the social host who loves ente... View Details

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$56,579
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2026 Tidewater 2110 Bay Max

$69,986

Fleming Island, FL
- Fleming Island, FL
- Fishing Bay / Flats / Skiff
- 21'
- 2026 / New
- $69,986
Looking for the ultimate all-in-one vessel for shallow-water angling and sunny weekend cruising? The Tidewater 2110 Bay Max is built for inshore anglers and adventure-loving famili... View Details

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$69,986
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2027 Bennington 22 S1 SWINGBACK

$71,950

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22'
- 2027 / New
- $71,950
If you are the designated social director of your friend group, the Bennington 22 S1 Swingback was built for you. Capable of hosting up to 12 people, this pontoon is ideal for tota... View Details

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$71,950
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2027 Bennington 22 S1 SWINGBACK

$76,644

Fleming Island, FL
- Fleming Island, FL
- Pontoon
- 22'
- 2027 / New
- $76,644
Imagine the ultimate weekend launchpad built specifically for social sun-seekers, water-sports enthusiasts, and big-crew entertainers. If your idea of a perfect day involves hostin... View Details

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$76,644
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2026 Chris Craft Sportster 28

$232,220

Fleming Island, FL
- Fleming Island, FL
- Cruiser
- 28'
- 2026 / New
- $232,220
Imagine cruising the waterways with style and a crowd. The Chris-Craft Sportster 28 Outboard is a fantastic choice for those who love to share their adventures on the water with fr... View Details

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$232,220
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Showing 862 to 882 of 1,194 boats found.

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