PRE-OWNED HARLEY-DAVIDSON® MOTORCYCLES


Explore affordable pre-owned Harley-Davidson® models at Woodstock Harley-Davidson® in Woodstock, IL

Looking for the perfect used powersports vehicle to get out on the trails? Or need a pre-owned motorcycle for commuting? Shop our entire selection of used powersports vehicles and motorcycles for sale at Woodstock Harley-Davidson!

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Showing 193 - 204 of 688 results
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Showing 193 - 204 of 688 results
  • FLHXS 2015 Street Glide® Special
    Call for price

    692807
    Pre-owned
    2015
    53129 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRM15FB692807
    UNKNOWN

    This US bestseller has proven itself across everything the 50 states have thrown at it, and now it’s ready to take on the rest of the world. This is a machine that’s every bit as comfortable with a trip to the office as it is with a grand tour.Last year’s Project Rushmore gave it its high output …

  • FLHXS 2016 Street Glide® Special $26,399.00 $16,999.00

    687272
    Pre-owned
    2016
    5500 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1KRM19GB687272
    Deep Jade Pearl

    You’re looking at the answer to the question, how do you fully load a touring bike with premium features and still roll with the stripped down bagger look? Check inside the sleek Project RUSHMORE batwing fairing and you’ll get an idea. Your looking at the top-of-the-line 6.5 inch touchscreen …

  • FLHXS 2017 Street Glide® Special $24,299.00 $15,999.00

    657933
    Pre-owned
    2017
    7033 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRC15HB657933
    Black Denim

    The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

  • FLHXS 2017 Street Glide® Special $23,699.00 $15,999.00

    680374
    Pre-owned
    2017
    14561 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRC10HB680374
    Black Denim

    The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

  • FLHXS 2017 Street Glide® Special $23,699.00 $17,999.00

    652905
    Pre-owned
    2017
    8914 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRC18HB652905
    Crushed Ice Pearl

    The Harley-Davidson® Street Glide Special model set the world standard for the stripped-down, hot rod look. Its style is often copied, but never duplicated. The all-new Milwaukee-Eight™ 107 engine backs up the look with massive torque. The ride is unmatched as well, thanks to the all-new suspension …

  • FLHXS 2018 Street Glide® Special $25,999.00 $19,999.00

    657245
    Pre-owned
    2018
    11756 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRC19JB657245
    Vivid Black

    When it comes to hot rod baggers, the Street Glide® Special is way out front. You get the tire-smoking power of its blacked-out Milwaukee-Eight® 107 engine sitting at the heart of dark finishes that stretch from headlight to exhaust. A new 19-inch Talon front wheel and 18-inch rear wheel. Stretched …

  • FLHXS 2018 Street Glide® Special $25,999.00 $20,999.00

    677538
    Pre-owned
    2018
    23657 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRC13JB677538
    Vivid Black

    When it comes to hot rod baggers, the Street Glide® Special is way out front. You get the tire-smoking power of its blacked-out Milwaukee-Eight® 107 engine sitting at the heart of dark finishes that stretch from headlight to exhaust. A new 19-inch Talon front wheel and 18-inch rear wheel. Stretched …

  • FLHXS 2019 Street Glide® Special $27,589.00 $20,499.00

    617894
    Pre-owned
    2019
    23384 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRP16KB617894
    Vivid Black

    The Street Glide® Special model kicks the hot rod bagger style into a higher gear. It starts with the Milwaukee-Eight® 114 (1868cc) engine that comes standard this year. When you twist the throttle, hold on tight. You also get the all-new, big screen BOOM! ™ GTS infotainment system. Then there’s …

  • FLHXS 2020 Street Glide® Special $29,999.00 $22,999.00

    600364
    Pre-owned
    2020
    6626 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1KRP10LB600364
    BILLIARD BURGANDY
  • FLHXS 2022 Street Glide® Special $24,999.00

    608872
    Pre-owned
    2022
    6923 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1KRP10NB608872
    White Sand Pearl

    The custom hot rod bagger look stops people in their tracks. Now powered up with the Milwaukee-Eight® 114 engine, you’ll leave them in your dust.

  • FLHXS 2022 Street Glide® Special $29,379.00 $22,999.00

    609697
    Pre-owned
    2022
    6865 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRP12NB609697
    White Sand Pearl

    The custom hot rod bagger look stops people in their tracks. Now powered up with the Milwaukee-Eight® 114 engine, you’ll leave them in your dust.

  • FLHXS 2023 Street Glide® Special $30,499.00 $22,499.00

    637468
    Pre-owned
    2023
    2482 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KRP12PB637468
    BIL BLU/BIL GRY

    This rare combo of performance, factory-custom bagger styling and cutting-edge connectivity celebrates 120 years of H-D craftsmanship and pride with commemorative paint and finishes.