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 85 - 96 of 688 results
  • FLHC 2026 Heritage Classic®
    Call for price

    TB036199
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YA91XTB036199
    Midnight Ember w/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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB036794
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YA912TB036794
    Midnight Ember w/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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB035389
    New
    2026
    6 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YA91XTB035389
    Teal Thunder / Vivid Black Black Cast 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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB035250
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YA911TB035250
    DRK BILIARD GRY

    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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB035010
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YA913TB035010
    Midnight Ember w/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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB035706
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YA917TB035706
    Vivid Black 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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB034612
    New
    2026
    4 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YA914TB034612
    DRK BILIARD GRY

    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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB032386
    New
    2026
    5 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YA910TB032386
    Vivid Black 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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB027795
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YA913TB027795
    Vivid Black 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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB032279
    New
    2026
    5 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YA91XTB032279
    Vivid Black 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 …

  • FLHC 2026 Heritage Classic®
    Call for price

    TB031420
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YA912TB031420
    Midnight Ember w/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 …

  • FLHCS 2018 Heritage Classic 114 $21,849.00 $12,999.00

    083833
    Pre-owned
    2018
    32709 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YBK12JC083833
    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 …