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Chaparral 21 SSI Boats For Sale

Chaparral Boats builds quality family boats in a variety of configurations like Ski & Wake, Deck Boats, Bowriders and Cruisers. They are among the leaders in sport boats and sport yachts ranging from 18' to 33'. Chaparall and Robalo boats are owned by the same parent company Marine Products Corporation. A close competing brand would be Sea Ray which builds a similar variety of boat types that are very stylish and well appointed. 

View a wide selection of 21 SSI boats from to .
21 SSI Boats For Sale
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    21 SSI
28 out of 12,231 Boats Found

28 out of 12,231 Boats Found

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  • 2025 Chaparral 21 SSi Ski & Fish

    2025 Chaparral 21 SSi Ski & Fish

    • $104,845
    • Somerset, KY
    $104,845
    • Length21'
    • Width0'
    • Conditionnew
    • Location Somerset, KY
    • $104,845
    • -- mi.

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

    View 190 Photos and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi Ski & Fish Somerset, KY
    $104,845
    Cruiser
    Somerset, KY
    --
  • 2025 Chaparral 21 SSi Ski & Fish

    2025 Chaparral 21 SSi Ski & Fish

    • $96,943
    • Somerset, KY
    $96,943
    • Length21'
    • Width0'
    • Conditionnew
    • Location Somerset, KY
    • $96,943
    • -- mi.

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

    View 103 Photos and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi Ski & Fish Somerset, KY
    $96,943
    Bowrider
    Somerset, KY
    --
  • 2025 Chaparral 21 SSI

    2025 Chaparral 21 SSI

    • $92,842
    • Somerset, KY
    $92,842
    • Length21'
    • Width0'
    • Conditionnew
    • Location Somerset, KY
    • $92,842
    • -- mi.

    2025 Chaparral 21 SSi OPTIONS ·         Mercury 4.5L MPI 1.62 Alpha 250 HP ·    &nb... View Details

    View 96 Photos and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSI Somerset, KY
    $92,842
    Bowrider
    Somerset, KY
    --
  • 2025 Chaparral 21 SSi

    2025 Chaparral 21 SSi

    • $75,165
    • Suamico, WI
    $75,165
    • Length21'
    • Width8'
    • Conditionnew
    • Location Suamico, WI
    • $75,165
    • -- mi.

    2025 Chaparral 21 SSiENDLESS POSSIBILITIES Everything that has made Chaparral's wildly popular SSi Series the talk of the waterways, gets bigger and... View Details

    View 39 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi Suamico, WI
    $75,165
    Bowrider
    Suamico, WI
    --
  • 2024 Chaparral 21 SSi Ski & Fish

    2024 Chaparral 21 SSi Ski & Fish

    • $71,830
    • Suamico, WI
    $71,830
    • Length21'
    • Width8'
    • Conditionnew
    • Location Suamico, WI
    • $71,830
    • -- mi.

    2024 Chaparral 21 SSi Ski & Fish Key Features: Folding Velocity Arch Tower Simrad GO9 Multifunction Chartplotter/Fishfinder with Engine Data and Aud... View Details

    View 38 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Ski & Fish Suamico, WI
    $71,830
    Bowrider
    Suamico, WI
    --
  • 2025 Chaparral 21 SSi OB (New) #N06474BT

    2025 Chaparral 21 SSi OB (New) #N06474BT

    • $71,635
    • Sterrett, AL
    $71,635
    • Length22'
    • Width0'
    • Conditionnew
    • Location Sterrett, AL
    • $71,635
    • -- mi.

    Mercury Four Stroke 150XL 150HP 25″ 150HPSimrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring –... View Details

    View 1 Photo and Details Contact Seller
    • Length22'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 22'
    22'
    Chaparral 21 SSi OB (New) #N06474BT Sterrett, AL
    $71,635
    Bowrider
    Sterrett, AL
    --
  • 2025 Chaparral 21 SSi OB (New) #N06400BT

    2025 Chaparral 21 SSi OB (New) #N06400BT

    • $71,365
    • Dadeville, AL
    $71,365
    • Length22'
    • Width0'
    • Conditionnew
    • Location Dadeville, AL
    • $71,365
    • -- mi.

    Simrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – SlateFolding Velocity Arch Tower – White... View Details

    View 13 Photos and Details Contact Seller
    • Length22'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 22'
    22'
    Chaparral 21 SSi OB (New) #N06400BT Dadeville, AL
    $71,365
    Bowrider
    Dadeville, AL
    --
  • 2025 Chaparral 21 SSi OB (New) #N06401BT

    2025 Chaparral 21 SSi OB (New) #N06401BT

    • $71,365
    • Sterrett, AL
    $71,365
    • Length22'
    • Width0'
    • Conditionnew
    • Location Sterrett, AL
    • $71,365
    • -- mi.

    Simrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – SlateFolding Velocity Arch Tower – White... View Details

    View 1 Photo and Details Contact Seller
    • Length22'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 22'
    22'
    Chaparral 21 SSi OB (New) #N06401BT Sterrett, AL
    $71,365
    Bowrider
    Sterrett, AL
    --
  • 2024 Chaparral 21 SSi

    2024 Chaparral 21 SSi

    • $70,005
    • Standish, ME
    $70,005
    • Length21'
    • Width8'
    • Conditionnew
    • Location Standish, ME
    • $70,005
    • -- mi.

    2024 Chaparral 21 SSiFeatures may include:Exterior Colors/GraphicsColor Selection for Hull Side Gelcoat with Color Matched Deck Graphics (Alloy Gray,... View Details

    View 8 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Standish, ME
    $70,005
    Bowrider
    Standish, ME
    --
  • 2025 Chaparral 21 SSi (New) #N06473BT

    2025 Chaparral 21 SSi (New) #N06473BT

    • $69,150
    • Sterrett, AL
    $69,150
    • Length21'
    • Width0'
    • Conditionnew
    • Location Sterrett, AL
    • $69,150
    • -- mi.

    Cockpit Interior (Cayenne White) upgradeMercruiser 4.5L MPI 1.62 Alpha 250 HP 250HPSimrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Trans... View Details

    View 1 Photo and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi (New) #N06473BT Sterrett, AL
    $69,150
    Bowrider
    Sterrett, AL
    --
  • 2025 Chaparral 21 SSi (New) #N06402BT

    2025 Chaparral 21 SSi (New) #N06402BT

    • $68,595
    • Sterrett, AL
    $68,595
    • Length21'
    • Width0'
    • Conditionnew
    • Location Sterrett, AL
    • $68,595
    • -- mi.

    Mercruiser 4.5L MPI 1.62 Alpha 250 HP 250HPSimrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring... View Details

    View 1 Photo and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi (New) #N06402BT Sterrett, AL
    $68,595
    Bowrider
    Sterrett, AL
    --
  • 2025 Chaparral 21 SSi (New) #N06403BT

    2025 Chaparral 21 SSi (New) #N06403BT

    • $68,595
    • Sterrett, AL
    $68,595
    • Length21'
    • Width0'
    • Conditionnew
    • Location Sterrett, AL
    • $68,595
    • -- mi.

    Mercruiser 4.5L MPI 1.62 Alpha 250 HP 250HPSimrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring... View Details

    View 1 Photo and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi (New) #N06403BT Sterrett, AL
    $68,595
    Bowrider
    Sterrett, AL
    --
  • 2025 Chaparral 21 SSi (New) #N06404BT

    2025 Chaparral 21 SSi (New) #N06404BT

    • $68,325
    • Sterrett, AL
    $68,325
    • Length21'
    • Width0'
    • Conditionnew
    • Location Sterrett, AL
    • $68,325
    • -- mi.

    Simrad GO9 Touch Multifunction Chartplotter/FishfinderClarion Transom RemoteSnap-In Seadek Cockpit Flooring – CayenneFolding Velocity Arch Tower – Whi... View Details

    View 1 Photo and Details Contact Seller
    • Length21'
    • Width0'
    • Conditionnew
    VIEW DETAILS
    2025 21'
    21'
    Chaparral 21 SSi (New) #N06404BT Sterrett, AL
    $68,325
    Bowrider
    Sterrett, AL
    --
  • 2024 Chaparral 21 SSi OB

    2024 Chaparral 21 SSi OB

    • $68,290
    • Leesburg, GA
    $68,290
    • Length21'
    • Width8'
    • Conditionnew
    • Location Leesburg, GA
    • $68,290
    • -- mi.

    *Vehicles are subject to prior sale. Unit is BLACK. Offer can be terminated without notice and images are for illustration purposes only, accessories... View Details

    View 68 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi OB Leesburg, GA
    $68,290
    Bowrider
    Leesburg, GA
    --
  • 2024 Chaparral 21 SSi

    2024 Chaparral 21 SSi

    • $68,289
    • Saint Joseph, MI
    $68,289
    • Length21'
    • Width8'
    • Conditionnew
    • Location Saint Joseph, MI
    • $68,289
    • -- mi.

    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. Trai... View Details

    View 33 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Saint Joseph, MI
    $68,289
    Bowrider
    Saint Joseph, MI
    --
  • 2024 Chaparral 21 SSi Ski & Fish

    2024 Chaparral 21 SSi Ski & Fish

    • $67,845
    • Standish, ME
    $67,845
    • Length21'
    • Width8'
    • Conditionnew
    • Location Standish, ME
    • $67,845
    • -- mi.

    2024 Chaparral 21 SSi Ski & FishFeatures may include:Exterior Colors/GraphicsColor Selection for Hull Side Gelcoat with Color Matched Deck Graphics (A... View Details

    View 11 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Ski & Fish Standish, ME
    $67,845
    Bowrider
    Standish, ME
    --
  • 2024 Chaparral 21 SSi

    2024 Chaparral 21 SSi

    • $66,910
    • Suamico, WI
    $66,910
    • Length21'
    • Width8'
    • Conditionnew
    • Location Suamico, WI
    • $66,910
    • -- mi.

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

    View 39 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Suamico, WI
    $66,910
    Bowrider
    Suamico, WI
    --
  • 2024 Chaparral 21 SSi

    2024 Chaparral 21 SSi

    • $66,360
    • Standish, ME
    $66,360
    • Length21'
    • Width8'
    • Conditionnew
    • Location Standish, ME
    • $66,360
    • -- mi.

    2024 Chaparral 21 SSiFeatures may include:Exterior Colors/GraphicsColor Selection for Hull Side Gelcoat with Color Matched Deck Graphics (Alloy Gray,... View Details

    View 11 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Standish, ME
    $66,360
    Bowrider
    Standish, ME
    --
  • 2024 Chaparral 21 SSi OB

    2024 Chaparral 21 SSi OB

    • $65,905
    • Standish, ME
    $65,905
    • Length21'
    • Width8'
    • Conditionnew
    • Location Standish, ME
    • $65,905
    • -- mi.

    2024 Chaparral 21 SSi OBEXTRAORDINARY EXCELLENCEWhen outboard power meets our 21 SSi, exellence awaits. Key options include snap-in SeaDek cockpit fl... View Details

    View 7 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi OB Standish, ME
    $65,905
    Bowrider
    Standish, ME
    --
  • 2024 Chaparral 21 SSi

    2024 Chaparral 21 SSi

    • $65,695
    • Standish, ME
    $65,695
    • Length21'
    • Width8'
    • Conditionnew
    • Location Standish, ME
    • $65,695
    • -- mi.

    2024 Chaparral 21 SSiFeatures may include:Exterior Colors/GraphicsColor Selection for Hull Side Gelcoat with Color Matched Deck Graphics (Alloy Gray,... View Details

    View 13 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2024 21'
    21'
    Chaparral 21 SSi Standish, ME
    $65,695
    Bowrider
    Standish, ME
    --
  • 2023 Chaparral 21 SSi Ski & Fish

    2023 Chaparral 21 SSi Ski & Fish

    • $65,034
    • Saint Joseph, MI
    $65,034
    • Length21'
    • Width8'
    • Conditionnew
    • Location Saint Joseph, MI
    • $65,034
    • -- mi.

    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... View Details

    View 33 Photos and Details Contact Seller
    • Length21'
    • Width8'
    • Conditionnew
    VIEW DETAILS
    2023 21'
    21'
    Chaparral 21 SSi Ski & Fish Saint Joseph, MI
    $65,034
    Fish & Ski
    Saint Joseph, MI
    --
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21 SSI Boats For Sale By Model (by popularity)

21 SSI Boats For Sale

New and Used 21 SSI Boats

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.