7 Best Used Harley Davidson For Sale Under $5,000

Harley Davidson under $5000 options are more available than many riders think. Are you looking for a used Harley Davidson for sale under 5000 without exceeding your budget? Look no further. We’ve compiled a comprehensive list of the best used Harley Davidson motorcycles that combine affordability and quality. Whether you’re seeking a classic cruiser with timeless style, a nimble motorcycle for urban streets, or a touring bike built for long rides, you’ll find a variety of options that suit your needs and budget.

Our selection includes bikes that have been well-maintained, offering excellent ride quality, reliability, and iconic Harley performance without the hefty sticker price of a brand-new model. Buyers should verify all payment data presented with the dealership’s sales representative before making a purchase. Some models may include available promotional programs, while others may list an ideal purchase price or require a down payment. Always review monthly payment data, destination charges, and other fees carefully to understand the final price.

Read on to discover detailed insights into each motorcycle, including specifications, mileage, and cruiser details, helping you make an informed decision to find your perfect ride at a pre owned price clear of surprises.

Top 7 Harley Davidson Under $5000

1. 2014 Harley Davidson FXST

With just $2,999, you can own the H-D FXST Softail Standard and have it delivered right to your garage. This model is a super solid ride known for its excellent performance, razor sharp handling, and smooth cruising ability.

It comes equipped with an aftermarket exhaust system that enhances both its sound and crisp throttle response, making every ride more enjoyable. The bike is built with classic softail lines that withstand harsh weather conditions and ensure long-term dependability.

This Softail Standard has been fully serviced and maintained, giving you peace of mind. As a test ride ready model, it is compatible with a wide range of Harley Davidson motorcycles aftermarket parts, allowing full customization. Whether you’re a seasoned rider or just getting started, the FXST Softail Standard delivers a confidence inspiring ride at an unbeatable pre owned price.

2. 2003 Harley Davidson Sportster 1200

Used like many other Harley Davidson under $5000 bikes, the 2003 Harley Davidson Sportster is an incredible product that gives great value for money at $4,250.

This particular model is the SPORTSTER 1200 ANNIVERSARY EDITION, made in 2003 to celebrate the milestone. The motorcycle’s engine is beautifully silver powder-coated, accentuated with lots of chrome details that give it a classic and stylish appearance. It has an engine mileage of 7,400 miles, reflecting moderate use and suggesting good remaining life.

Moreover, the 2003 Harley Davidson Sportster comes equipped with forward foot controls, which offer a more comfortable riding position for long rides. It also features cooler and lower-profile rear shock absorbers that improve ride quality and handling. The stylish buckhorn handlebars add to the bike’s vintage charm while providing better control and comfort for the rider.

This model is well-regarded for its reliable V-Twin engine, known for delivering a smooth yet powerful ride experience. It’s a perfect choice for riders looking for a classic Harley with solid performance and iconic design, all available within an affordable budget. Whether you’re a new rider or a seasoned enthusiast, this Sportster Anniversary Edition offers a blend of tradition and functionality that stands out in the used motorcycle market under $5,000.

3. 2011 Harley Davidson XL 1200C Sportster

The 2011 XL 1200C Sportster Custom combines cruiser CVO styling with modern upgrades. Its 1,200cc V-Twin provides smooth yet powerful performance. With 11,619 miles and fresh servicing—including Michelin tires, spark plugs, and brake fluids—it’s test ride ready.

It features two tone paint schemes, Harley accessories valued at $3,500, a Screamin’ Eagle Stage One Kit for enhanced crisp throttle response, and a windshield for comfort in hot and heavy traffic. Add-ons like LED lighting, tail bag, and engine guards make this a factory custom bagger-inspired model.

At $4,950, this Sportster represents an ideal purchase price for riders who want only the essentials plus tasteful upgrades.

4. 1995 Harley Davidson Sportster 883 Hugger

This 1995 Hugger is a pre owned Harley that feels like new. With just 5,618 miles, garage-kept care, and extras like new plugs, factory manual, and Screamin’ Eagle exhaust, it offers great value at $2,200.

The Hugger delivers a confidence inspiring ride with its low center frame design, making it approachable for urban riders and trike adventure seekers. Its classic softail lines and original pipes give it authentic Harley DNA.

For those looking for a test ride ready bike with timeless charm, this is a right bike at the right pre owned price.

5. 2007 Harley Davidson Sportster 1200 Sport

For $4,000, the 2007 Sportster 1200 Sport offers a strong 1200cc engine and ergonomically sound chassis. With 34,799 miles, it still provides reliable performance for commuters and riders tackling heavy traffic daily.

The bike comes with a charger, helping ensure you’re always test ride ready in less than a minute. Its ride quality appeals to urban riders, while its nimble motorcycle handling makes it a great choice for new and experienced riders alike.

At this pre owned location, it’s offered OBO, making it a flexible and affordable way to own a Harley.

6. 1999 Harley Davidson Softail Custom

This used Harley Davidson FXST Softail Custom features a 1350cc engine, 69,000 miles, and a glass sparkle black bodywork look enhanced with a mean-sounding exhaust. At $2,500, it’s a strong contender for riders wanting highway shredding power.

It features a custom fuel tank with stretched range (200 miles) and sporty two-up seating. With its classic softail lines and aggressive look, it balances heritage and modern features.

A test ride on this bike proves why it’s still a poster bike for Harley enthusiasts searching motorcycles for sale at the best pre owned price.

7. 2008 Harley Davidson Sportster

Priced at $4,250, the 2008 Sportster XL1200C offers 8,177 miles, ESPFI fuel system, and disc brakes for reliability. Its two tone paint schemes and chrome wheels reflect Harley’s classic appeal.

Features like forward foot controls, chrome-laced wheels, and a slotted rear wheel make this a blacked out Harley Davidson alternative with cruiser details intact. Its ride quality and sportster legacy design make it perfect for urban riders or long trips.

For those comparing to a Honda Shadow Phantom, Indian Motorcycle, or Kawasaki Polaris, the Sportster remains the right bike.

Conclusion

If you’re searching used Harley Davidson for sale under 5000, these motorcycles for sale prove you don’t need to overspend. From naked sportbike looks to cruiser CVO vibes, Harley Davidson offers something for every rider.

Whether browsing Bluegrass Harley Davidson, Toledo Harley Davidson, or checking listings powered by Dealer Spike, be sure to review monthly payment disclaimer, applicable tag, and available promotional programs carefully. Consider credit history, down payment, and actual payment to calculate your final price—don’t rely on just the vehicle page or search active filters.

Each of these used Harley Davidson motorcycles delivers confidence inspiring rides, grand American design, and a chance to enjoy the Harley lifestyle at a pre owned price clear of hidden costs. For urban riders, long-distance travelers, and those chasing a trike adventure, the right Harley is waiting.

So start browsing your nearest pre owned location, compare against rivals like the Suzuki Triumph XXX Yamaha, Shadow Phantom, or even the Fat Bob, and take your dream Harley for a test ride today. With careful research, the vehicle featured calculate and pre owned price ensure you’ll find the right bike with the thrill of Harley Davidson ownership—without breaking the bank.

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