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  • 2025 Chaparral 21 SSi Ski & Fish Unique Key Features 5 Year Premium Level Limited Component Warranty Battery On/Off Switch Built-In Livewell Under Rear Bench Seat Deep F... View Details

    $104,845
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  • 2025 Chaparral 21 SSi Ski & Fish OPTIONS ·         Mercury 4.5L MPI 1.62 Alpha 250 HP ·       &... View Details

    $96,943
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  • 2025 Chaparral 21 SSi OPTIONS ·         Mercury 4.5L MPI 1.62 Alpha 250 HP ·         Hull Sid... View Details

    $92,842
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  • 2025 Chaparral 21 SSiENDLESS POSSIBILITIES Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 21 SSi... View Details

    $75,165
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  • 2024 Chaparral 21 SSi Ski & Fish Key Features: Folding Velocity Arch Tower Simrad GO9 Multifunction Chartplotter/Fishfinder with Engine Data and Audio Controls 70 Quart Built-in... View Details

    $71,830
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  • Arriving soon, see this new 2025 Chaparral 21 SSi! How much fun can you pack into one summer? Plenty, aboard your new Chaparral. Trailerable to your favorite destinations. Nimble,... View Details

    $71,619
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  • Simrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – SlateFolding Velocity Arch Tower – WhiteCockpit and Bow CoverAnchor –... View Details

    $70,879
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  • Price Drop

    2024 Chaparral 21 SSiENDLESS POSSIBILITIES Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and better with the amazing 21 SSi... View Details

    $70,245
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  • Mercury Four Stroke 150XL 150HP 25″ 150HPSimrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – CayenneFolding Velocity Arch... View Details

    $69,635
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  • Simrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – SlateFolding Velocity Arch Tower – WhiteCockpit and Bow CoverAnchor –... View Details

    $69,365
    VIEW DETAILS
  • Cockpit Interior (Cayenne White) upgradeMercruiser 4.5L MPI 1.62 Alpha 250 HP 250HPSimrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpi... View Details

    $69,150
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  • *Vehicles are subject to prior sale. Unit is BLACK. Offer can be terminated without notice and images are for illustration purposes only, accessories shown in pictures are not incl... View Details

    $68,290
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  • Now available, in our showroom, see this new 2024 Chaparral 21 SSi! How much fun can you pack into one summer? Plenty, aboard your new Chaparral. Trailerable to your favorite desti... View Details

    $68,289
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  • 2024 Chaparral 21 SSi Ski & FishFeatures may include:Exterior Colors/GraphicsColor Selection for Hull Side Gelcoat with Color Matched Deck Graphics (Alloy Gray, Biscayne Blue, Blac... View Details

    $67,845
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  • Simrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – SlateFolding Velocity Arch Tower – WhiteCockpit and Bow CoverAnchor –... View Details

    $66,325
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  • 2024 Chaparral 21 SSi OBEXTRAORDINARY EXCELLENCEWhen outboard power meets our 21 SSi, exellence awaits. Key options include snap-in SeaDek cockpit flooring , a swim platform mat a... View Details

    $65,905
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  • 2022 Chaparral 21 SSi OB One of Chaparrals most popular models, offered for sale by original owner and in exceptional condition.  Meticulous maintenance and all the preferre... View Details

    $64,999
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  • Price Drop

    Chaparral's Ski and Fish is boating's most versatile 21-footer! This is the very best combination of convenient convertability from family runabout to fishing fun. Plushly appointe... View Details

    $64,899
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  • 2024 Chaparral 21 SSi OB Ski & FishREFINED EXELLENCE Valued for its versatility and innovation, the 21 SSi Outboard Ski & Fish is both a first-rate fishing machine and a power-pac... View Details

    $63,920
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  • 2023 Chaparral 21 SSiFeatures may include:Exterior Colors/GraphicsColor Selection for Hull Side Gelcoat with Color Matched Deck Graphics (Alloy Gray, Biscayne Blue, Black, Fire Red... View Details

    $57,999
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  • Price Drop

    Stock #430478 Video of this vessel available at www [dot] popsells [dot] com/view/430478 Reason for selling is "Not In Use Anymore.". ANY and ALL offers will be put in front of... View Details

    $50,000
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1 to 21 of 27 boats found.

21 SSi Boats On Boatcrazy

Chaparral has been building boats since 1965. Starting in Fort Lauderdale, they moved to Nashville, Georgia in 1976, after needing larger premises.

Since then they have become one of the most respected names in the boating industry and one of the world's leading manufacturers of quality fiberglass boats. Chaparral builds a wide variety of boats, from Ski & Wake, Deck Boats, Bowriders, and Cruisers, and each one is built with the same attention to detail and commitment to quality, using state-of-the-art technology in their design process.

Search for your next Chaparral on Boatcrazy.com

21 SSi Boats Frequently Asked Questions

Chaparral boats are in the mid to upper mid-price range but they also have an entry-level line. You can view a wide selection of Chaparral boats on Boatcrazy from $5,999 to $371,999.

Chaparral boats are built with a deep V-plane which adds weight to the boat adding stability in the water, the engines are also optimized for fuel efficiency. Their line-up includes; Ski & Wake, Deck Boats, Bowriders, and Cruisers.

Chaparral produces a number of line series; SSI, SSX, OSX, SURF and VORTEX. Some of their more popular models are; 220 SSI, 257 SSX, Surf, 310 SIGNATURE, and the 23 SSI

Chaparral builds boats for all types of water activities and recreational boating. From day cruising and overnight cruising to freshwater and saltwater fishing. All watersports including wakeboarding, water skiing, and towable family fun.