10 Old Harley-Davidson Motorcycles You Can Buy For Dirt Cheap

Owning a Harley-Davidson has long been considered a rite of passage for motorcycle enthusiasts — but the dream often stalls the moment you see the price tag on a new one. Here’s the good news: the used market is packed with genuine Harleys that won’t drain your savings account. While brand-new Harley motorcycles come with premium price tags, the used motorcycle market is still full of some great deals — as long as you do some digging, you can find plenty of choices.

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It’s important to note that finding a good used motorcycle always depends on the right balance between age, mileage, and price. For this list of cheap used Harley-Davidsons, we’re not talking about vintage or collectible Harleys, and that’s why we are sticking to bikes that are under 25 years old. Our criteria were to find reliable, affordable bikes from 2000 model years and newer that still have plenty of life left in them. We also set some ground rules to narrow down our choices. Every bike on this list is available for under $5,000, has between 25,000 and 75,000 miles (so you’re not getting a beater), and can be found on Cycle Trader right now if you do a nationwide search.

Whether you’re after a stylish cruiser, a lightweight city bike, or a long-haul touring machine, these 10 Harleys offer an authentic experience without the hefty price tag.

2017 Harley-Davidson 750 Street

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While Harley-Davidson is known for making some massive cruisers, the American motorcycle maker also briefly experimented with smaller-capacity machines. The Street 500 and 750 models were primarily aimed at developing markets worldwide, but they were also targeted toward newer riders in America. The Street 750 in particular was a pocket rocket, and if you’re looking for an affordable, entry-level Harley, it’s a fantastic choice. Built for urban riders who prefer agility, comfort, and Harley-Davidson style without the bulk of a big V-twin cruiser, it stands apart from most bikes you’ll see on highways across the country. This little bike features a liquid-cooled 749cc Revolution V-Twin, making it more forgiving in stop-and-go traffic. It’s also one of the lightest Harleys ever made, which makes handling a breeze for new riders. The Street 750’s sleek design and blacked-out styling give it a modern look that resonates with younger riders, and finding a newer 2017 model for under $5k is very easy.

2015 Harley-Davidson Iron 883

Harley-Davidson

Moving up in size, the Iron 883 is a fan-favorite among many riders as well. The Iron 883 has always been an affordable, no-nonsense bobber-style motorcycle. This Sportster model has been stripped down to the essentials, with blacked-out components, a peanut fuel tank, and mid-mounted foot controls for a more aggressive riding position. It’s not the ideal highway cruiser, but it has plenty of character and will give you the full Harley experience even when riding around town. The 2015 Iron 883’s air-cooled Evolution V-Twin engine delivers a raw, old-school riding experience, and the platform is easy to personalize with a wide range of aftermarket parts. If you want a Harley that looks badass, sounds mean, and doesn’t cost a fortune, the Iron 883 is an excellent choice.

2011 Harley-Davidson SuperLow

Harley-Davidson

For riders who want something more comfortable than an Iron 883, the SuperLow is the answer. Older model years such as 2011 can be found for as little as $3k. As the name suggests, the SuperLow features a low seat height, making it ideal for shorter riders and beginners. It also gets a smoother suspension setup than the standard Sportster models, making it slightly more comfortable on longer rides. This is a great option for anyone looking to transition from smaller bikes into the Harley world without feeling overwhelmed by weight and size.

2006 Harley-Davidson Heritage Softail Classic

Harley-Davidson

Now we’re heading into big-bike territory. If you’re looking for something with classic cruiser styling and modern comfort, older Heritage Softail Classic model years deliver the goods. A solid 2006 example can be found for under $5k, and you still get a bike equipped with a big windshield, leather saddlebags, floorboards, and a relaxed riding position — everything you need for long highway rides. The Softail frame mimics the hardtail look of vintage Harleys while incorporating hidden rear suspension for a smoother ride. It’s a great bargain for those who want the full cruiser experience without shelling out big money for a brand-new model, which can sometimes run north of $20k.

2003 Harley-Davidson Low Rider

Harley-Davidson

The Dyna family includes some of the most beloved Harley models, like the Super Glide, Low Rider, and Wide Glide. These bikes have a more aggressive, raw riding feel, making them great for riders who want old-school Harley character. You can find 2003 model year Low Riders for under $5k, and these bikes are not only fun to ride — they make you feel like a badass as you slice through the open road. If you want a bike that can serve as both a cruiser and a performance machine, the Dyna models are the way to go.

2002 Harley-Davidson Road Glide

Harley-Davidson

If you want the biggest and baddest of them all, the Road Glide is without a doubt one of Harley’s best touring motorcycles ever. A true highway warrior in every sense, the Road Glide is perfect for riders who love long-distance cruising on a comfortable and luxurious motorcycle. The frame-mounted fairing makes it more aerodynamically stable at high speeds, reducing wind buffeting compared to fork-mounted fairings. The Road Glide has been around since 1998 and was specifically built for comfort, with a relaxed riding position, saddlebags, and excellent wind protection. While modern Road Glides will set you back a small fortune, older models from 2002 onward can be found for under $5k, making them among the most accessible old-school big Harleys on the used market.

2004 Harley-Davidson V-Rod

Harley-Davidson

If you want an iconic Harley-Davidson that makes a strong statement, look no further than the first-gen V-Rod. This motorcycle is unlike any other Harley. It was co-developed with Porsche engineers and features a liquid-cooled, high-revving engine that produces more horsepower than any other bike on this list. It’s a muscle cruiser with sportbike-like performance, making it the best Harley on this list for speed lovers. It was a truly special motorcycle when it launched, and it remains one of the most revolutionary Harley-Davidson models ever built. Fortunately, these bikes haven’t appreciated by astronomical figures, and you can still find an older 2004 model for under $5k — which is pretty hard to believe.

2008 Harley-Davidson Fat Boy

Harley-Davidson

One of the most famous Harley-Davidson names is the Fat Boy. The Softail model was introduced in 1990 and quickly grew into a fan favorite among riders who craved both power and style. The Fat Boy has undergone some major design changes over the years, but the older models offered retro charm backed by serious performance. A 2008 Fat Boy came equipped with Twin Cam engines, and those V-Twins delivered the raw thrills that many riders still seek out today. If you want a legendary Harley-Davidson motorcycle with commanding road presence and genuine muscle, the Fat Boy will earn you plenty of attention and keep you grinning mile after mile.

2014 Harley-Davidson Fat Bob

Harley-Davidson

Another bold motorcycle from Harley-Davidson is the Fat Bob. This Dyna model has attitude to spare. Its design broke from tradition with dual headlights, chunky tires, and surprisingly capable cornering ability, making it a fantastic all-around machine. Introduced in 2008, the Fat Bob is a relatively modern entry in the lineup, and a 2014 model can easily be had for under $5k. This model year also features the much-loved Twin Cam engine, offering raw power and the classic Harley feel.

2018 Harley-Davidson SuperLow

Harley-Davidson

The most recent model on this list is another SuperLow. If you’d prefer a motorcycle that’s no more than a few years old and still feels contemporary, a 2018 SuperLow can be yours for right around $5k. The newer SuperLows are more refined, comfortable, and easier to handle than their predecessors. While the SuperLow isn’t a large motorcycle — it sits within the Sportster lineup — it’s still a fantastic choice for Harley lovers on a budget. It’s easy to ride, dependable, has plenty of power, and it looks pretty darn good too.