Filter Boats By

Filters

from

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
12 out of 12,482 Boats Found

Let’s talk about pre-qualifying for a boat loan

Boat ownership has never been more affordable or easier. Whether you are looking to purchase a new boat or refinance your existing loan, we can help.

Back
Filter
  • Price Drop
    2025 Chaparral 21 SSI

    2025 Chaparral 21 SSI

    $73,825
    Somerset, KY
    • Somerset, KY
    • Wakeboard
    • 21' / 0'
    • 2025 / New
    • $73,825

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

    View 96 Photos and Details Contact Seller
    $73,825
    VIEW DETAILS
  • 2025 Chaparral 21 SSi

    2025 Chaparral 21 SSi

    $72,840
    Standish, ME
    • Standish, ME
    • Bowrider
    • 21' / 8'
    • 2025 / New
    • $72,840

    2025 Chaparral 21 SSiENDLESS POSSIBILITIESEverything 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

    View 1 Photo and Details Contact Seller
    $72,840
    VIEW DETAILS
  • Price Drop
    2025 Chaparral 21 SSi

    2025 Chaparral 21 SSi

    $72,010
    Standish, ME
    • Standish, ME
    • Bowrider
    • 21' / 8'
    • 2025 / New
    • $72,010

    2025 Chaparral 21 SSiENDLESS POSSIBILITIESEverything 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

    View 18 Photos and Details Contact Seller
    $72,010
    VIEW DETAILS
  • 2025 Chaparral 21 SSi

    2025 Chaparral 21 SSi

    $71,619
    Saint Joseph, MI
    • Saint Joseph, MI
    • Bowrider
    • 21' / 8'
    • 2025 / New
    • $71,619

    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

    View 18 Photos and Details Contact Seller
    $71,619
    VIEW DETAILS
  • Price Drop
    2025 Chaparral 21 SSi

    2025 Chaparral 21 SSi

    $70,840
    Standish, ME
    • Standish, ME
    • Bowrider
    • 21' / 8'
    • 2025 / New
    • $70,840

    2025 Chaparral 21 SSiENDLESS POSSIBILITIESEverything 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

    View 17 Photos and Details Contact Seller
    $70,840
    VIEW DETAILS
  • 2023 Chaparral 21 SSi

    2023 Chaparral 21 SSi

    $57,999
    Osage Beach, MO
    • Osage Beach, MO
    • Bowrider
    • 21' / 8'
    • 2023 / Used
    • $57,999

    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

    View 29 Photos and Details Contact Seller
    $57,999
    VIEW DETAILS
  • Price Drop
    2022 Chaparral 21 SSi

    2022 Chaparral 21 SSi

    $50,000
    Austin, TX
    • Austin, TX
    • Bowrider
    • 21' / 0'
    • 2022 / Used
    • $50,000

    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

    View 10 Photos and Details Contact Seller
    $50,000
    VIEW DETAILS
  • 2020 Chaparral 21 SSI

    2020 Chaparral 21 SSI

    $49,900
    Gold Canyon, AZ
    • Gold Canyon, AZ
    • Bowrider
    • 21' / 0'
    • 2020 / Used
    • $49,900

    Stock #399099 Video of this vessel available at www [dot] popsells [dot] com/view/399099 Reason for selling is "Not using as much as planned". ANY and ALL offers will be put in... View Details

    View 10 Photos and Details Contact Seller
    $49,900
    VIEW DETAILS
  • 2021 Chaparral 21 SSI

    2021 Chaparral 21 SSI

    $48,495
    Winthrop Harbor, IL
    • Winthrop Harbor, IL
    • Runabout
    • 21' / 0'
    • 2021 / Used
    • $48,495

    Like new 2021 Chaparral 21 SSI with wakeboard tower & trailer included! Don't miss this like new 2021 Chaparral 210 SSI, a premium bowrider that delivers exceptional performanc... View Details

    View 10 Photos and Details Contact Seller
    $48,495
    VIEW DETAILS
  • 2020 Chaparral 21 SSi

    2020 Chaparral 21 SSi

    $47,800
    Magnolia, TX
    • Magnolia, TX
    • Bowrider
    • 21' / 0'
    • 2020 / Used
    • $47,800

    Stock #441411 Video of this vessel available at www [dot] popsells [dot] com/view/441411 Reason for selling is "Not used anymore". This Chaparral has been on the market for more... View Details

    View 10 Photos and Details Contact Seller
    $47,800
    VIEW DETAILS
  • Price Drop
    2020 Chaparral 21ssi

    2020 Chaparral 21ssi

    $41,750
    Hallsville, TX
    • Hallsville, TX
    • Bowrider
    • 21' / 0'
    • 2020 / Used
    • $41,750

    Stock #431771 Video of this vessel available at www [dot] popsells [dot] com/view/431771 ANY and ALL offers will be put in front of our seller! Submit your offer today! Good and... View Details

    View 10 Photos and Details Contact Seller
    $41,750
    VIEW DETAILS
  • 2022 Chaparral 21 SSI

    2022 Chaparral 21 SSI

    $26,999
    Hilton Head Island, SC
    • Hilton Head Island, SC
    • Bowrider
    • 21' / 0'
    • 2022 / Used
    • $26,999

    Stock #428974 Reason for selling is "Updating Fleet". ANY and ALL offers will be put in front of our seller! Submit your offer today! Good condition, 12 person capacity, & 150HP... View Details

    View 10 Photos and Details Contact Seller
    $26,999
    VIEW DETAILS
Showing 1 to 12 of 12 boats found.

Chaparral Boats For Sale By Model (by popularity)

Chaparral Boats For Sale

New and Used Chaparral Boats

Chaparral 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

Chaparral 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.