Sportster® Motorcycles For Sale in Milwaukee, WI & Chicago, IL

2006 Harley-Davidson® Sportster® 883 Custom The only thing better than a street bike is a custom street bike, like the Sportster® 883 Custom. Harley-Davidson® begins by giving it the smooth, rubber-mounted Evolution engine and 4.5-gallon tank.

2007 Harley-Davidson® Sportster® 883 All 2007 Sportster® 883 models are retuned for increased performance, including this most affordable Harley-Davidson® model. New cams and Electronic Sequential Port Fuel Injection (ESPFI) enable the Sportster® 883 to generate more torque at lower rpms, giving the rider greatly improved throttle response and bet...

2009 Harley-Davidson® Sportster® 1200 Custom Packing plenty of power and just the right mix of chrome, the Sportster® 1200 Custom stays true to its name. With a new lighter-weight chrome Slotted Disc Cast Aluminum rear wheel, chrome Laced Steel 21-inch front wheel with new fender, chrome engine highlights, chrome handlebar and headlight, and a pol...

2007 Harley-Davidson® Sportster® 1200 Custom A powerful performer that goes the distance in style, the XL Sportster® 1200 Custom features a 4.5-gallon fuel tank and fuel-injected XL Evolution™ 1200cc engine. New gauges include a clock, low-fuel warning light and two trip set odometers, while longer handlebar wires provide more customization option...

2006 Harley-Davidson® Sportster® 1200 Custom Something about the 1200 Custom pulls you in. At first glance, you see it in the swept-back handlebar, pullback riser and bullet-style headlight. But you can’t quite put your finger on it. Then you check out the wheels. Chrome Slotted Disc with wide tire in back. Laced wheel up front. Center stage sits ...

2007 Harley-Davidson® Sportster® 1200 Nightster™ An iron fist in a soft-bellied world. With enough grit to put the edge back on a blade, it's the rawest bare-knuckled 1200cc Sportster® model yet. Chopped front and rear fenders. Side-mount license plate. Stop-tail-turn lights. Low 25.3" seat height. Old School front fork gaiters. Rawboned graphics ...

2007 Harley-Davidson® Sportster® 1200 Custom A powerful performer that goes the distance in style, the XL Sportster® 1200 Custom features a 4.5-gallon fuel tank and fuel-injected XL Evolution™ 1200cc engine. New gauges include a clock, low-fuel warning light and two trip set odometers, while longer handlebar wires provide more customization option...

2014 Harley-Davidson® Sportster® SuperLow® Smooth travel riding suspension, comfortable cruising position and easy handling for endless miles. The 2014 Harley-Davidson® Sportster® SuperLow® XL883L has all the motorcycle features you want for easy handling beginner motorcycle. This easy to ride motorcycle offered at an affordable price makes this m...

2012 Harley-Davidson® Sportster® ™ The 2012 Harley-Davidson® Sportster® Nightster™ XL1200N has a unique Dark Custom style. From front to back, this bike has a vintage motorcycle look. This Dark Custom has several custom styling features that all add up to a stripped down, minimalist, vintage motorcycle look. Medium gray 1200cc engine with polished...

2012 Harley-Davidson® Sportster® ™ The 2012 Harley-Davidson® Sportster® Nightster™ XL1200N has a unique Dark Custom style. From front to back, this bike has a vintage motorcycle look. This Dark Custom has several custom styling features that all add up to a stripped down, minimalist, vintage motorcycle look. Medium gray 1200cc engine with polished...

2006 Harley-Davidson® Sportster® 883 R Take a look at what just came down victory lane. The Sportster® 883R model is back, cleaner and meaner than ever. Wide rear tire and fender. Staggered shorty dual exhaust pipes. Two-up seat with passenger pegs. Dual disc brakes up front. We stayed true to the authentic H-D racing look, available in three sche...

2013 Harley-Davidson® Sportster® Forty-Eight® The 2013 Harley-Davidson® Sportster® Forty-Eight® model XL1200X is one of the garage custom motorcycles in the Harley® Dark Custom line. This bike cruises down the road with a 1200 cc Evolution engine – an engine with a true Harley-Davidson® soul. New for 2013, the Harley-Davidson® Forty-Eight® model c...

2017 Harley-Davidson® Iron 883™ Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street. A great leap forward in the dark arts. You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, it has only gotten better. ...

2016 Harley-Davidson® Sportster® Iron 883™ Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street. A great leap forward in the dark arts. It was one of the early Dark Custom™ motorcycles. A dark pioneer of raw, blacked-out, stripped-down custom aggression. So the ques...

2015 Harley-Davidson® Sportster® Iron 883™ This blacked-out bruiser is a raw, aggressive throwback. No apologies—just an authentic ride. The 2015 Harley-Davidson® Sportster® Iron 833™ model XL883N is an amazing way to get started with a custom bobber. From the authentic Harley® 883 cc engine to the chopped fenders to the peanut fuel tank, every pi...

2015 Harley-Davidson® Sportster® Iron 883™ This blacked-out bruiser is a raw, aggressive throwback. No apologies—just an authentic ride. The 2015 Harley-Davidson® Sportster® Iron 833™ model XL883N is an amazing way to get started with a custom bobber. From the authentic Harley® 883 cc engine to the chopped fenders to the peanut fuel tank, every pi...

2013 Harley-Davidson® Sportster® Iron 883™ The 2013 Harley-Davidson® Sportster® Iron 833™ model XL883N is an amazing way to get started with a custom motorbike. From the authentic Harley® 883 cc engine to the chopped fenders to the peanut fuel tank, every piece of the Harley® Sportster® Iron 883™ model has the style you want in your custom motorbi...

2017 Harley-Davidson® Iron 883™ Aggressive throwback styling taken to a place altogether new. No need to shine this machine. Just get on and tear up the nearest street. A great leap forward in the dark arts. You’re looking at a pioneer of raw, blacked-out, stripped-down custom style. In the years since its introduction, it has only gotten better. ...

2018 Harley-Davidson® Sportster® Forty-Eight® Special A new school twist on the choice ride for those who know how to have fun. Features may include: 1200 Evolution® engine 1200cc at your command to deliver tons of torque for an unforgettably fun ride. Dark Custom Style A balance of blacked-out and chrome finishes give it that authentic custom att...

2015 Harley-Davidson® Sportster® SuperLow® Smooth riding suspension, comfortable cruising position and easy handling for endless miles. Features May Include: Premium Styling Features The value and quality of the confidence-inspiring SuperLow® model is unparalleled in its class. With a true Harley-Davidson rumble, steel parts, premium paint and fla...