Boats for sale in Chicago Illinois - BoatCrazy

1,508 boats found within 100 miles out of 15,282 Boats Found

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2025 Harris 230 Cruiser

$69,615

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $69,615
Act fast on this limited-time offer! Experience Unmatched Adventure Introducing the 2025 Harris 230 Cruiser CWDH, where luxury meets performance on the water. Crafted for those who... View Details

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$69,615
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2025 Barletta LUSSO25UE

$141,296

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $141,296
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UE Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$141,296
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2025 Barletta LUSSO25UC

$137,288

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $137,288
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UC Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$137,288
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2025 Barletta LUSSO23UC

$114,732

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 23' / 0'
- 2025 / New
- $114,732
Contact us to find out ALL available savings! BARLETTA LUSSO 25 UC Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$114,732
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2025 Barletta ARIA20CC

$48,131

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 20' / 0'
- 2025 / New
- $48,131
Contact us to find out ALL available savings! BARLETTA ARIA 20 CC Everything you love about the Barletta DNA with a price conscious approach. Is the Aria right for you? Designed to... View Details

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$48,131
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2025 Barletta LUSSO23UC

$137,834

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2025 / New
- $137,834
Contact us to find out ALL available savings! BARLETTA LUSSO 23 UC Is Lusso right for you? Designed with you, and your on-water experience, in mind, the Barletta Lusso models offer... View Details

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$137,834
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2026 Yamaha SX195

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Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2026 / New
- Call for price
Introducing the 2026 Yamaha SX195, built to elevate your weekends. Experience unrivaled supercharged performance, striking styling, and exceptional value in its class. Key Features... View Details

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2022 Mastercraft XT 24

$149,980

Pewaukee, WI
- Pewaukee, WI
- Ski & Wake
- 24' / 0'
- 2022 / Used
- $149,980
366 Hours Explore the 2022 Masc XT 24 Step aboard the 2022 Masc XT 24, where luxury meets performance on the water. This stunning vessel, available at SkipperBud's Pewaukee in Pewa... View Details

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$149,980
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2026 Barletta S22QC

$71,967

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 22' / 0'
- 2026 / New
- $71,967
Experience Unmatched Luxury The 2026 Barletta SANZA22QC is the epitome of luxury on water, designed for those who appreciate the finer things in life. Crafted with meticulous atten... View Details

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$71,967
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2026 Yamaha SX190

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 19' / 0'
- 2026 / New
- Call for price
Immerse Yourself in Luxury Introducing the 2026 Yamaha 190SX, a stunning blend of performance and elegance that invites you to embark on unforgettable water adventures. With its sl... View Details

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2026 Yamaha 195S

$60,305

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2026 / New
- $60,305
Introducing the 2026 Yamaha 195S, affordable luxury features at 19-feet. High-tech features, sleek design, and top-notch performance create the ultimate affordable 19-foot boat pac... View Details

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$60,305
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2026 Yamaha AR195

$58,085

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 19' / 0'
- 2026 / New
- $58,085
Introducing your 2026 Yamaha AR195, supercharge your Saturdays. Enjoy unparalleled supercharged performance, standout styling, and incredible value, all enhanced by a watersports t... View Details

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$58,085
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2025 Cruisers 60 CANTIUS

$2,549,000

Pewaukee, WI
- Pewaukee, WI
- Yacht
- 60' / 0'
- 2025 / Used
- $2,549,000
Just Listed: 2025 Cruisers Yachts 60 Cantius – Virtually New. Freshwater. Fully Loaded. Step aboard this titled, never-used 2025 Cruisers Yachts 60 Cantius — a yacht that has never... View Details

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$2,549,000
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2026 Yamaha 252S

$108,310

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 25' / 0'
- 2026 / New
- $108,310
Act fast on this limited-time offer! Experience the Ultimate Luxury on Water Step aboard the 2026 Yamaha 252S, where unparalleled performance meets exquisite craftsmanship. This ne... View Details

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$108,310
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2026 Barletta Lusso 23 UC

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Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 27' / 0'
- 2026 / New
- Call for price
Is the Lusso right for you? Designed wth you and your on-water experience in mind, the Barletta Lusso models offer something for everyone. A classic and Stylish Rail-set, Ultra-sof... View Details

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2026 Barletta Lusso 23 QCSS

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Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 25' / 0'
- 2026 / New
- Call for price
Is the Lusso right for you? Designed wth you and your on-water experience in mind, the Barletta Lusso models offer something for everyone. A classic and Stylish Rail-set, Ultra-sof... View Details

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2022 Mastercraft X22

$149,995

Pewaukee, WI
- Pewaukee, WI
- Wakeboard
- 22' / 0'
- 2022 / Used
- $149,995
2022 Mastercraft X22 View Details

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$149,995
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2026 Yamaha SX220

$66,613

Pewaukee, WI
- Pewaukee, WI
- Cruiser
- 22' / 0'
- 2026 / New
- $66,613
Introducing the 2026 Yamaha SX220, unmatched value, versatility, and affordability. With its roomy cockpit, abundant storage, and fuel-efficient dual engines, this boat offers exce... View Details

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$66,613
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2026 Barletta Lusso 23 QCSS

$153,042

Pewaukee, WI
- Pewaukee, WI
- Other / Not Classified
- 25' / 0'
- 2026 / New
- $153,042
Act fast on this limited-time offer! Experience the Exhilaration The 2026 Barletta LUSSO23QCSS is more than just a boat; it's your ticket to unforgettable adventures on the water.... View Details

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$153,042
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2026 Barletta Lusso 25 U

$151,055

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 27' / 0'
- 2026 / New
- $151,055
Act fast on this limited-time offer! Discover the Elegance of Luxury Experience the pinnacle of aquatic opulence with the 2026 Barletta LUSSO25U, now available at SkipperBud's Pewa... View Details

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$151,055
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2026 Barletta Lusso 25 UE

Call for price

Pewaukee, WI
- Pewaukee, WI
- Pontoon
- 27' / 0'
- 2026 / New
- Call for price
Is the Lusso right for you? Designed wth you and your on-water experience in mind, the Barletta Lusso models offer something for everyone. A classic and Stylish Rail-set, Ultra-sof... View Details

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Showing 1345 to 1365 of 1,508 boats found.

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