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 325 - 336 of 688 results
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Showing 325 - 336 of 688 results
  • FXBB 2026 Street Bob®
    Call for price

    TB033070
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ910TB033070
    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.

  • FXBB 2026 Street Bob®
    Call for price

    TB030066
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YJ915TB030066
    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

    TB028222
    New
    2026
    4 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YJ915TB028222
    DRK BILIARD GRY

    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

    TB032807
    New
    2026
    5 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ919TB032807
    DRK BILIARD GRY

    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

    TB025714
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    1HD1YJ910TB025714
    DRK BILIARD GRY

    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.

  • FXBBS 2022 Street Bob® 114 $15,349.00 $12,995.00

    056888
    Pre-owned
    2022
    22200 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YYK14NB056888
    GAUNT GRY MTLIC

    The lightest-weight Softail equipped with a Milwaukee-Eight® 114 engine for a quick and nimble ride with power to spare. A perfect performance base for customization with 2-up seating, black steel laced wheels and dark finishes deliver no nonsense, Raw Bobber attitude.

  • FXBBS 2022 Street Bob® 114 $15,349.00 $13,495.00

    063613
    Pre-owned
    2022
    2090 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YYK10NB063613
    Redline Red

    The lightest-weight Softail equipped with a Milwaukee-Eight® 114 engine for a quick and nimble ride with power to spare. A perfect performance base for customization with 2-up seating, black steel laced wheels and dark finishes deliver no nonsense, Raw Bobber attitude.

  • FXBBS 2022 Street Bob® 114 $16,749.00 $11,999.00

    NB050844
    Pre-owned
    2022
    1609 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YYK19NB050844
    Vivid Black

    The lightest-weight Softail equipped with a Milwaukee-Eight® 114 engine for a quick and nimble ride with power to spare. A perfect performance base for customization with 2-up seating, black steel laced wheels and dark finishes deliver no nonsense, Raw Bobber attitude.

  • FXBBS 2024 Street Bob™ 114 $17,349.00 $15,499.00

    018920
    Pre-owned
    2024
    22962 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1YYK17RB018920
    Vivid Black

    A perfect performance base for customization, the Harley-Davidson® Street Bob 114 is a blacked-out gritty, lean, and mean bobber.

  • FXBR 2024 Breakout™ 117 $22,499.00 $20,499.00

    049726
    Pre-owned
    2024
    3757 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YEZ16RB049726
    Vivid Black

    Dripping with chrome, the Harley-Davidson® Breakout 117 is a raked-out cruiser that packs Milwaukee-Eight® 117 V-Twin muscle.

  • FXBR 2024 Breakout™ 117 $23,149.00 $20,999.00

    044125
    Pre-owned
    2024
    51 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    1HD1YEZ1XRB044125
    White Onyx Pearl

    Dripping with chrome, the Harley-Davidson® Breakout 117 is a raked-out cruiser that packs Milwaukee-Eight® 117 V-Twin muscle.

  • FXBR 2024 Breakout™ 117 $22,699.00 $19,999.00

    046864
    Pre-owned
    2024
    1967 mi
    Harley-Davidson®
    Illinois Harley-Davidson®
    1HD1YEZ13RB046864
    Vivid Black

    Dripping with chrome, the Harley-Davidson® Breakout 117 is a raked-out cruiser that packs Milwaukee-Eight® 117 V-Twin muscle.