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 589 - 600 of 688 results
  • Harley-Davidson® Street Glide® 2026 FLHX AURORA BLUE DNM
    Call for price

    TB600737
    New
    2026
    6 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KB713TB600737
    Aurora Blue Denim Chrome Trim

    For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

  • Harley-Davidson® Street Glide® 2026 FLHX BLOOD ORANGE
    Call for price

    TB605928
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KB712TB605928
    Blood Orange Black Trim

    For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

  • Harley-Davidson® Street Glide® 2026 FLHX DRK BILIARD GRY
    Call for price

    TB615387
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KB710TB615387
    DRK BILIARD GRY

    For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

  • Harley-Davidson® Street Glide® 2026 FLHX DRK BILIARD GRY
    Call for price

    TB614284
    New
    2026
    56 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KB717TB614284
    DRK BILIARD GRY

    For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

  • Harley-Davidson® Street Glide® 2026 FLHX MIDNIGHT EMBER
    Call for price

    TB613901
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1KB710TB613901
    Midnight Ember Chrome Trim

    For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

  • Harley-Davidson® Street Glide® 2026 FLHX Midnight Ember Chrome Trim
    Call for price

    TB615101
    New
    2026
    6 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KB710TB615101
    Midnight Ember Chrome Trim
  • Harley-Davidson® Street Glide® 2026 FLHX PURPLE ABYSS
    Call for price

    TB604491
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1KB716TB604491
    Purple Abyss Black Trim

    For those who’d rather roam than simply arrive, the 2026 Street Glide delivers the edge of the map on a silver platter. With striking new colorways, a liquid-cooled Milwaukee-Eight® 117 motor, ride-tuned rear suspension optimized for long haul comfort, and the 12.3” Skyline™ OS (312 mm) display …

  • Harley-Davidson® Street Glide® Special 2015 FLHXS BLACK W/ PINSTRIPE $23,599.00 $13,495.00

    657706
    Pre-owned
    2015
    33360 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRM10FB657706
    Black Denim

    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 …

  • Harley-Davidson® Street Glide® Special 2015 FLHXS BLACK W/ PINSTRIPE $23,599.00 $12,499.00

    682043
    Pre-owned
    2015
    62391 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRM14FB682043
    Black Denim

    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 …

  • Harley-Davidson® Street Glide® Special 2017 FLHXS BLACK $26,899.00 $18,499.00

    666248
    Pre-owned
    2017
    1312 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KRC12HB666248
    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 …

  • Harley-Davidson® Street Glide® Special 2017 FLHXS BLACK $18,999.00
    MSRP: $21,450.00

    655926
    Pre-owned
    2017
    24471 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1KRC19HB655926
    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 …

  • Harley-Davidson® Street Glide® Special 2018 FLHXS LEGEND BLUE DNM $26,699.00 $16,999.00

    625936
    Pre-owned
    2018
    52063 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1KYC15JB625936
    Legend Blue Denim

    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 …