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 637 - 648 of 688 results
  • RA1250S 2026 Pan America® 1250 Special
    Call for price

    TS303897
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    MLY1ZES14TS303897
    Blood Orange Black Cast Wheels

    From city slab to backcountry rock, the Pan America 1250 Special delivers 150 hp of adaptable power at the flick of the throttle, in a package that weighs less than 570 lbs. With Adaptive Ride Height, Rider Safety Enhancements, and a 173 mm touchscreen display all standard, it’s packed with tech …

  • RA1250S 2026 Pan America® 1250 Special
    Call for price

    TS305386
    New
    2026
    10 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    MLY1ZES10TS305386
    Blood Orange Black Cast Wheels

    From city slab to backcountry rock, the Pan America 1250 Special delivers 150 hp of adaptable power at the flick of the throttle, in a package that weighs less than 570 lbs. With Adaptive Ride Height, Rider Safety Enhancements, and a 173 mm touchscreen display all standard, it’s packed with tech …

  • RA1250ST 2026 Pan America® 1250 ST
    Call for price

    TS308067
    New
    2026
    1 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    MLY1ZJS19TS308067
    Vivid Black Black Trim

    The 2026 Pan America 1250 ST is for riders who know the best stories aren't told in a straight line. Featuring a 150 hp Revolution Max® motor, the new clutchless Quick Shifter, Adaptive Ride Height, all-new ride modes, and industry-standard 432 mm wheels for easy customisation, it’s a street-tuned, …

  • RA1250ST 2026 Pan America® 1250 ST
    Call for price

    TS307730
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    MLY1ZJS19TS307730
    Aurora Blue Denim Black Trim

    The 2026 Pan America 1250 ST is for riders who know the best stories aren't told in a straight line. Featuring a 150 hp Revolution Max® motor, the new clutchless Quick Shifter, Adaptive Ride Height, all-new ride modes, and industry-standard 432 mm wheels for easy customisation, it’s a street-tuned, …

  • RA1250ST 2026 Pan America® 1250 ST
    Call for price

    TS305461
    New
    2026
    4 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    MLY1ZJS19TS305461
    Aurora Blue Denim Black Trim

    The 2026 Pan America 1250 ST is for riders who know the best stories aren't told in a straight line. Featuring a 150 hp Revolution Max® motor, the new clutchless Quick Shifter, Adaptive Ride Height, all-new ride modes, and industry-standard 432 mm wheels for easy customisation, it’s a street-tuned, …

  • RH1250S 2021 Sportster® S $15,349.00 $11,999.00

    B318162
    Pre-owned
    2021
    6500 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZC414MB318162
    Vivid Black

    A new chapter opens in H-D’s longest running family, powered by the all-new Revolution® Max 1250T. To call it the ultimate Sportster® is an understatement. Prepare for a level of power and performance that has surpassed all expectations.

  • RH1250S 2023 Sportster® S $16,399.00 $12,999.00

    309767
    Pre-owned
    2023
    10239 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZC419PB309767
    Vivid Black

    A new chapter opens in H-D’s longest running family, powered by the all-new Revolution® Max 1250T. To call it the ultimate Sportster® is an understatement. Prepare for a level of power and performance that has surpassed all expectations.

  • RH1250S 2023 Sportster® S $16,849.00 $13,999.00

    302243
    Pre-owned
    2023
    4033 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    1HD1ZC416PB302243
    Vivid Black

    A new chapter opens in H-D’s longest running family, powered by the all-new Revolution® Max 1250T. To call it the ultimate Sportster® is an understatement. Prepare for a level of power and performance that has surpassed all expectations.

  • RH1250S 2026 Sportster® S
    Call for price

    TS304453
    New
    2026
    3 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    MLY1ZC414TS304453
    White Onyx Pearl Black Trim

    With 121 hp from the liquid-cooled Revolution Max® 1250T motor, a wide front tire, 2-1-2 scrambler-style exhaust, and suspension tuned for performance and comfort, the 2026 Sportster S reimagines classic styling with sharp, modern intent.

  • RH1250S 2026 Sportster® S
    Call for price

    TS303849
    New
    2026
    2 mi
    Harley-Davidson®
    Windy City Harley-Davidson®
    MLY1ZC412TS303849
    DRK BILIARD GRY

    With 121 hp from the liquid-cooled Revolution Max® 1250T motor, a wide front tire, 2-1-2 scrambler-style exhaust, and suspension tuned for performance and comfort, the 2026 Sportster S reimagines classic styling with sharp, modern intent.

  • RH1250S 2026 Sportster® S
    Call for price

    TS303339
    New
    2026
    2 mi
    Harley-Davidson®
    Woodstock Harley-Davidson®
    MLY1ZC411TS303339
    DRK BILIARD GRY

    With 121 hp from the liquid-cooled Revolution Max® 1250T motor, a wide front tire, 2-1-2 scrambler-style exhaust, and suspension tuned for performance and comfort, the 2026 Sportster S reimagines classic styling with sharp, modern intent.

  • RH1250S 2026 Sportster® S
    Call for price

    TS305009
    New
    2026
    10 mi
    Harley-Davidson®
    Chicago Harley-Davidson®
    MLY1ZC411TS305009
    Blood Orange Black Trim

    With 121 hp from the liquid-cooled Revolution Max® 1250T motor, a wide front tire, 2-1-2 scrambler-style exhaust, and suspension tuned for performance and comfort, the 2026 Sportster S reimagines classic styling with sharp, modern intent.