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

2008 Harley-Davidson® Sportster® 1200 Low The 1200 Low offers all of the performance of a fuel-injected 1200cc Evolution™ V-Twin™, with pull-back handlebar and a low 26.3 seat height for comfortable ergonomics and a 4.5-gallon fuel tank for increased range. Black 13-spoke Cast Aluminum 19-inch front wheel is only available on this Sportster model....

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.

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...

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.

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. ...

2009 Harley-Davidson® Sportster® 1200 Low Offering a preferred blend of performance, agility and ergonomics, the Sportster® 1200 Low adds a recalibrated suspension and tire-hugging front fender for 2009. Powered by a fuel-injected 1200cc Evolution V-Twin™ engine, the 1200 Low also features a pull-back handlebar, a low 26.3-inch seat height, and a ...

2019 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Now with fresh, new graphics. Features may include: TEAR UP THE NEAREST STREETS WITH RAW CUSTOM STYLE BLACKED-OUT LOOK It’s the poster bike o...

2018 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. Features may include: Blacked-Out Look It’s the poster bike of the anti-chrome movement. You’ve got a black powder-coated 883cc engine with black rocker covers. Black on...

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. ...

2019 Harley-Davidson® Sportster® SuperLow® LET THE MILES ROLL BY WITH THIS EASY RIDER You’ll feel the confidence that comes from its low seat, well-balanced stance and low center of gravity. Easy handling, and comfort to go all day. Features may include: NOTHING PUTS YOU CLOSER TO THE ROAD COMFORTABLE COCKPIT The low bucket seat, longer travel rea...

2016 Harley-Davidson® Sportster® Forty-Eight® The redesigned 2016 Forty-Eight® motorcycle comes at you with more low-slung Dark Custom™ attitude than ever, from its fat front end to its new cast aluminum wheels. We didn’t rebuild it. We reloaded it. The first time the world saw this gas tank was 1948. But the world has never seen that iconic tank ...

2020 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson® Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Features may include: Blacked-Out Look It’s the poster bike of the anti-chrome movement. You’ve got a black powder-coated 883cc engine with ...

2020 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson® Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Features may include: Blacked-Out Look It’s the poster bike of the anti-chrome movement. You’ve got a black powder-coated 883cc engine with ...

2020 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson® Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Features may include: Blacked-Out Look It’s the poster bike of the anti-chrome movement. You’ve got a black powder-coated 883cc engine with ...

2019 Harley-Davidson® Sportster® Iron 1200™ THE THRILL OF RIDING STRIPPED TO ITS BARE ESSENCE A modern take on what’s been putting big grins on the faces of Sportster® motorcycle riders for decades. Features may include: THROWBACK STYLING. THROW YOUR HEAD BACK POWER. 1200CC EVOLUTION™ ENGINE 1200cc at your command to deliver tons of torque for an ...

2019 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Now with fresh, new graphics. Features may include: TEAR UP THE NEAREST STREETS WITH RAW CUSTOM STYLE BLACKED-OUT LOOK It’s the poster bike o...

2019 Harley-Davidson® Sportster® Iron 883™ EVERYTHING YOU NEED, NOTHING YOU DON’T An original icon of the Harley-Davidson Dark Custom style. It sets the standard for the raw, stripped-down, blacked-out look. Now with fresh, new graphics. Features may include: TEAR UP THE NEAREST STREETS WITH RAW CUSTOM STYLE BLACKED-OUT LOOK It’s the poster bike o...

2016 Harley-Davidson® Roadster™ The new Roadster™ motorcycle combines stoplight-to-stoplight power, agility and garage-built custom style to shatter every mold. Tucked in, fast back style and corner cranking torque for a street eating machine. The new Roadster™ puts a powerful new level of sport into the Sportster® line-up. Its refined performance...

2012 Harley-Davidson® Sportster® 1200 Custom The 2012 Harley-Davidson® Sportster® 1200 Custom XL1200C is a true Harley® Sportster® custom motorcycle, just a little fatter and a little more custom than the other Sportsters. The fat front tire wrapped around a 16-inch wheel gives it a cool custom look and offers nimble handling. Stylistic components...