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 229 - 240 of 688 results
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Showing 229 - 240 of 688 results
  • FLSL 2019 Softail Slim® $16,349.00 $13,499.00

    063477
    Pre-owned
    2019
    5223 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YDJ29KB063477
    Bonneville Salt Denim

    The stripped-down, souped-up, post WWII era look of the bobber is running stronger than ever in the Softail Slim® model. You get the classic look of spoked wheels, chopped mudguards and footboards. And a ride straight out of right now. It’s 16 kilograms lighter, with greater lean angle, than Slim …

  • FLSTC 2008 Heritage Softail® Classic $18,600.00 $7,999.00

    Y039045
    Pre-owned
    2008
    18381 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BW5458Y039045
    CPR/BLK
  • FLSTC 2009 Heritage Softail® Classic $12,999.00 $8,499.00

    065923
    Pre-owned
    2009
    15885 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1BW5189Y065923
    BLACK W/PINSTRIPE

    Rolling on new signature wide whitewall tyres, the Heritage Softail Classic receives a number of other more-subtle styling changes and new components that shift this popular model in a new, even more retro direction for 2009. The beefy FL front end features a front fender and chrome headlight …

  • FLSTC 2009 Heritage Softail® Classic $17,999.00 $8,999.00

    047066
    Pre-owned
    2009
    38493 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1BW51X9Y047066
    BLACK W/PINSTRIPE

    Rolling on new signature wide whitewall tyres, the Heritage Softail Classic receives a number of other more-subtle styling changes and new components that shift this popular model in a new, even more retro direction for 2009. The beefy FL front end features a front fender and chrome headlight …

  • FLSTC 2009 Heritage Softail® Classic $18,854.00 $9,499.00

    Y052293
    Pre-owned
    2009
    32821 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BW5129Y052293
    BLACK W/PINSTRIPE

    Rolling on new signature wide whitewall tyres, the Heritage Softail Classic receives a number of other more-subtle styling changes and new components that shift this popular model in a new, even more retro direction for 2009. The beefy FL front end features a front fender and chrome headlight …

  • FLSTC 2014 Heritage Softail® Classic $19,479.00 $10,999.00

    019745
    Pre-owned
    2014
    33927 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BWV14EB019745
    BIG BLUE/V BLK W/ PINSTRIPE

    The 2014 Heritage Softail® Classic blends its retro looks with today's technology to offer modern touring capabilities. Powered by an air-cooled Twin Cam 103™ engine with Six-Speed Cruise Drive transmission, it provides more performance power for passing, hill-climbing, and riding with passenger …

  • FLSTC 2014 Heritage Softail® Classic $19,479.00 $10,999.00

    EB036949
    Pre-owned
    2014
    9626 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BWV16EB036949
    BIG BLUE/V BLK W/ PINSTRIPE

    The 2014 Heritage Softail® Classic blends its retro looks with today's technology to offer modern touring capabilities. Powered by an air-cooled Twin Cam 103™ engine with Six-Speed Cruise Drive transmission, it provides more performance power for passing, hill-climbing, and riding with passenger …

  • FLSTC 2015 Heritage Softail® Classic $19,499.00 $11,999.00

    020486
    Pre-owned
    2015
    32551 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BWV19FB020486
    Vivid Black

    The perfect marriage of styling that dates back 80-odd years, and technology that’s bang up to date. With its classy whitewalls, full fenders and leather-studded saddlebags, the Heritage gives you 40s styling in spades.This year we’ve improved the braking system to give it an even better feel with …

  • FLSTC 2015 Heritage Softail® Classic $18,999.00 $10,999.00

    016453
    Pre-owned
    2015
    25427 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1BWV17FB016453
    Morocco Gold Pearl

    The perfect marriage of styling that dates back 80-odd years, and technology that’s bang up to date. With its classy whitewalls, full fenders and leather-studded saddlebags, the Heritage gives you 40s styling in spades.This year we’ve improved the braking system to give it an even better feel with …

  • FLSTC 2016 Heritage Softail® Classic $17,349.00 $12,495.00

    041206
    Pre-owned
    2016
    22295 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1BWV31GB041206
    Superior Blue

    The Heritage Softail® Classic drips with the nostalgia of days gone by, but that’s only half of the equation for the rider of today. The hidden suspension gives you the authentic look without the bone-shaking ride of an old Hardtail. You get the comfort of cruise control for those long stretches of …

  • FLSTF 2007 Fat Boy® $17,420.00 $9,999.00

    044844
    Pre-owned
    2007
    14996 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1BX5127Y044844
    MAROON
  • FLSTF 2007 Fat Boy® $17,095.00 $8,999.00

    035936
    Pre-owned
    2007
    24130 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1BX5167Y035936
    RED PEARL