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!

page_info Filter by
Price
Year
Mileage
Length
CLEAR ALL CLEAR FILTERS
Showing 301 - 312 of 688 results
page_infoFilters
Showing 301 - 312 of 688 results
  • FXBB 2020 Street Bob® $16,144.00 $12,999.00

    075281
    Pre-owned
    2020
    19702 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJJ19LB075281
    River Rock Gray

    The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

  • FXBB 2020 Street Bob® $14,599.00 $12,999.00

    066784
    Pre-owned
    2020
    3983 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJJ11LB066784
    BRACUDA SLV DNM W/PINSTRIPE

    The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

  • FXBB 2020 Street Bob® $15,549.00 $12,999.00

    LB031329
    Pre-owned
    2020
    14923 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJJ10LB031329
    BRACUDA SLV DNM W/PINSTRIPE

    The Street Bob® model gives you the two-fists-in-the wind riding experience stripped down to the bare essence. Blacked out surfaces, spoked wheels, hidden digital instrumentation, forward controls, and chopped mudguards. The 107-cubic inch (1745cc) Milwaukee-Eight® engine gives you all the power …

  • FXBB 2025 Street Bob™ $17,199.00 $15,999.00

    033542
    Pre-owned
    2025
    2596 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ916SB033542
    Iron Horse Metallic w/Cast Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBB 2025 Street Bob™ $17,999.00 $15,999.00

    012532
    Pre-owned
    2025
    259 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ918SB012532
    Billiard Gray w/Cast Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBB 2025 Street Bob™ $18,999.00 $15,999.00

    012128
    Pre-owned
    2025
    205 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ911SB012128
    Vivid Black w/Laced Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBB 2025 Street Bob™ $18,999.00 $15,999.00

    042068
    Pre-owned
    2025
    283 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ915SB042068
    Billiard Gray w/Cast Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBB 2025 Street Bob™ $17,399.00 $16,999.00

    SB018364
    Pre-owned
    2025
    98 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJ91XSB018364
    Billiard Gray w/Cast Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBB 2025 Street Bob™ $17,399.00 $15,999.00

    010288
    Pre-owned
    2025
    1035 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YJ912SB010288
    Billiard Gray w/Cast Wheels

    The Street Bob is a lean, mean bobber with mini-ape handlebars, mid-mounted foot controls, and a massive Milwaukee-Eight® 117 Classic V-twin, which makes the slim-but-tough Softail® quicker than ever.

  • FXBB 2026 Street Bob®
    Call for price

    TB038248
    New
    2026
    4 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ917TB038248
    Aurora Blue Denim Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®
    Call for price

    TB032271
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ915TB032271
    Olive Steel Metallic Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.

  • FXBB 2026 Street Bob®
    Call for price

    TB031346
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ915TB031346
    Vivid Black Chrome Cast Wheels

    The 2026 Street Bob is lean by design and loaded up where you need it. With a Milwaukee-Eight 117 motor, torque-tuned 2-into-1 exhaust, updated 4” analog gauge, USB-C charging, and standard Rider Safety Enhancements, it leaves the frills on the factory floor but doesn’t skimp.