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 73 - 84 of 688 results
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Showing 73 - 84 of 688 results
  • FLD 2012 Switchback™ $14,999.00 $8,999.00

    319630
    Pre-owned
    2012
    67645 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1GZM13CC319630
    EMBR RED SUNGLO

    The Dyna® Switchback™ is custom touring motorcycle with detachable hard saddlebags and quick-detach windshield. Remove those components in just seconds to turn the Switchback into a custom street cruiser. Chassis, suspension and tires are engineered to deliver light, confident handling.The …

  • FLD 2014 Switchback™ $15,849.00 $8,499.00

    322252
    Pre-owned
    2014
    40284 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1GZM18EC322252
    BLACK

    The 2014 Switchback with detachable saddlebags and windshield is perfect for both cruising and touring. Powered by a Twin Cam 103™ engine with smooth shifting Six-Speed Cruise Drive transmission and with a light-weight chassis and cast aluminium wheels, the Switchback offers easy-handling. Its 2-…

  • FLFB 2025 Fat Boy® $23,249.00 $21,999.00

    039908
    Pre-owned
    2025
    218 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YF911SB039908
    Vivid Black

    Adored since day one, the singular Fat Boy stands out with bright chrome and bold finishes, and now it is better than ever with a big Milwaukee-Eight® 117 Custom V-twin engine.

  • FLFB 2025 Fat Boy® $22,799.00 $21,999.00

    SB020001
    Pre-owned
    2025
    363 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YF91XSB020001
    Whiskey Fire / Vivid Black

    Adored since day one, the singular Fat Boy stands out with bright chrome and bold finishes, and now it is better than ever with a big Milwaukee-Eight® 117 Custom V-twin engine.

  • FLFB 2026 Fat Boy®
    Call for price

    TB033731
    New
    2026
    6 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YF910TB033731
    DRK BILIARD GRY

    Wide tires front and back. Classic Lakester cast aluminum wheels. The iconic steamroller stance, backed by a Milwaukee-Eight® 117 motor. LED lighting all around, Rider Safety Enhancements standard, and fine factory details that honor one of Harley-Davidson’s most legendary silhouettes. The 2026 Fat …

  • FLFBS 2019 Fat Boy® 114 $20,849.00 $14,999.00

    019987
    Pre-owned
    2019
    14689 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YGK2XKB019987
    Scorched Orange/Black Denim

    The name may be Fat Boy®, but the look is all muscle. This is the icon, riding on a 240mm rear tyre, 160mm front tyre and solid disc wheels. You get satin chrome finishes and signature LED lighting. This version is 14 kilograms lighter than the previous generation Fat Boy models, and its slinging …

  • FLFBS 2020 Fat Boy® 114 $21,949.00 $16,999.00

    LB012674
    Pre-owned
    2020
    7588 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YGK18LB012674
    Stiletto Red

    The name may be Fat Boy®, but the look is all muscle. This is the icon, riding on a 240mm rear tyre, 160mm front tyre and solid disc wheels. You get satin chrome finishes and signature LED lighting. This version is 14 kilograms lighter than the previous generation Fat Boy models, and its slinging …

  • FLFBS 2023 Fat Boy® 114 $20,399.00 $14,999.00

    047003
    Pre-owned
    2023
    15627 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YGK17PB047003
    Bright Billiard Blue

    The original fat custom icon. Now lighter than the previous generation Fat Boy 114, and slinging torque from a Milwaukee-Eight® 114. You’ll feel the difference the instant you crack the throttle.

  • FLFBS 2024 Fat Boy™ 114 $21,999.00 $18,999.00

    017290
    Pre-owned
    2024
    1703 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YGK13RB017290
    Red Rock

    The original fat custom icon. Loved since day one, the Harley-Davidson® Fat Boy 114 stands out with bright chrome and bold finishes.

  • FLHC 2018 Heritage Classic $19,949.00 $11,995.00

    073795
    Pre-owned
    2018
    16421 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YAJ19JC073795
    INDGRYDNM/BLKDM W/PINSTRIPE

    The Heritage Softail® Classic used to be an homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that. The history is still there, and now it’s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a …

  • FLHC 2018 Heritage Classic $19,949.00 $13,999.00

    029384
    Pre-owned
    2018
    24807 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YAJ1XJC029384
    Silver Fortune

    The Heritage Softail® Classic used to be an homage to ‘50s chrome nostalgia. Take a look at the new one, and you’ll see it’s anything but that. The history is still there, and now it’s done with a dark style and a modern edge and a totally reinvigorated ride. At the heart of it all, you get a …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB036279
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YA918TB036279
    Brilliant Red Black Laced Wheels

    The 2026 Heritage Classic is the perfect blend of vintage soul with modern muscle. We’ve packed a Milwaukee-Eight® 117 motor into its low-slung frame and mated it to a performance-tuned 2-into-1 exhaust that makes it a monster. It also comes with lockable symmetrical saddlebags, LED lighting all …