14 Used Harleys Worth Every Penny (And 3 To Avoid At All Costs)

14 Used Harleys Worth Every Penny (And 3 To Avoid At All Costs)

Harley-Davidson is one of the oldest motorcycle companies and has a very loyal fan base.

Harley-Davidson is one of the oldest motorcycle companies and has a very loyal fan base. Consumers generally love or hate Harley – or even a bit of both. But no one can deny the company has produced some legendary cruisers. Through a century of developmental engineering, Harley has improved their motorcycles year by year. As a result, they have produced some of the best touring bikes that give other top brands like Triumph Motorcycles and Royal Enfield a run for their money.

Updated March 2023: Due to their timeless designs and rugged features, Harley-Davidsons are one of the most popular motorcycles to buy used. However, these bikes also have a long list of issues that have caused recalls and a negative reputation. So, we’ve updated the list of great used Harley choices for 2023 and also added a few more models we’d stay away from.

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For a dark period during the 1970s, Harley belonged to American Machine and Foundry (AMF) and their production was ineffective and lacked quality control. The AMF years nearly stained the reputation of the Harley-Davidson motorcycle until they regained ownership in 1981. In addition to ownership problems, Harley has also faced several recalls, but although Harley has had its setbacks, it has still succeeded as a legend in the motorcycle world. But thinking that all Harley-Davidson models are great is a big mistake. So, to help steer motorcycle fans in the right direction, here’s a list of 14 used Harleys worth every penny and three to avoid at all costs.



17 One Of The Best: 2009-2010 Harley-Davidson Fat Bob – $11,000

14 Used Harleys Worth Every Penny (And 3 To Avoid At All Costs)
American Motorcycle Trading Company 

Not only is the Fat Bob arguably one of the best Harley-Davidsons ever built, but from a starting price of roughly $25,000, used ones in pristine shape go for $10,000-$11,000. Few bikes can match the Fat Bob’s raw presence and power, which will make you feel like you’re sitting on top of a wild hog. This is definitely a Harley worth investing in.

16 One Of The Best: 2001 Harley-Davidson XL Sportster – $5,000

2001 Harley-Davidson XL Sportster

How could it not be worth it? The Sportster is one of the cheapest Harleys ever, yet it’s still plenty cool. It’s nothing fancy, offering rugged looks and up to 48 horsepower and 50 lb-ft of torque in the 883cc spec and 66 hp and 73 lb-ft for the 1200cc bikes. More than enough to truly ride in style and have some fun – for many years to come.

15 One Of The Best: 2006 Harley-Davidson FXSTS Springer Softail – $9,155

2006 Harley-Davidson FXSTS Springer Softail Via Only Motorbikes
Only Motorbikes

The 2006 FXSTS Springer Softail may be the greatest Softail that Harley-Davidson has ever made. The FXSTS comes with simple styling to enable personalization and customization that Softail owners enjoy. The bike proved its durability on the market. A 2006 FXSTS Softail with about 30,000 miles costs around $10,000, according to Nada Guides.

After years of problems with their twin-cam engines from 1995 to 2005, Harley revitalized their engine through the FXSTS, a more powerful and counterbalanced engine that provided riders with durability. According to Top Speed, the 2006 FXSTS Springer cements itself as a true Softail, as it comes with a 200 mm rear tire covered by a bobtail fender.

14 One Of The Best: 2012 Harley-Davidson FLHR Road King – $11,510

2012 Harley-Davidson FLHR Road King
Manchester Harley-Davidson 

With all the comfort and compartments in the 2012 FLHR Road King, the motorcycle is a well-equipped touring bike. After reinventing their twin-cam engine, Harley-Davidson was able to optimize the opportunity to redesign the Road King with a 1690cc engine and six-speed transmission. This bike comes with many features according to Top Speed: a six-gallon fuel tank, an anti-lock braking system, and cruise control. The Road King has always been one of the best Harleys, as it received a 4 out of 5-star rating on Motorcycle News. With a six-gallon tank, it is the perfect choice for a long cruise on the highway.

RELATED: How Porsche-Powered Harley-Davidson Superbikes Almost Happened In The 70s

13 One Of The Best: 2011 Harley-Davidson FLSTC Heritage Softail Classic – $9,720

2011 Harley-Davidson FLSTC Heritage Softail Classic
American Motorcycle Trading Company 

With a low price tag, the 2011 Harley-Davidson Heritage Softail Classic comes with comfortable seating to provide a smooth ride. The motorcycle ranks higher than the average touring bike in every category, according to Bikez. This Harley is one of the best touring bikes ever made by the company and makes a great used purchase.

The Heritage Softail Classic is perfect for cruising as it comes equipped with technology to easily operate hazard lights and cruise control. The bike’s design offers a taste of the past and comes fan-friendly with leather saddles and chrome-laced wheels.

12 One Of The Best: 2014 Harley-Davidson FXDWG Dyna Wide Glide – $12,000

2014 Harley Davidson Dyna Wide Glide fxdwg
American Motorcycle Trading Company

The Dyna Wide Glide is a rider’s dream. The bike has many customizable features and the captivating looks of a true cruiser. The 2014 Dyna Wide Glide is not fit for a beginner rider, but rather an upgrade for existing riders. Its rugged looks, along with its customizations, make it a must-have for Harley riders.

RELATED: 10 Most Badass Cruiser Bikes To Buy In 2023

The twin-cam engine on the Dyna Wide Glide was finally mastered in 2014 after years of failure. Now, the reinvented twin-cam provides durability for riders. According to Nada Guides, it costs $12,000. For that price, it’s a high-quality motorcycle for a low-cost buy.

11 One Of The Best: 2008 Harley-Davidson FXSTC Softail Custom – $7,000

2008 Harley-Davidson FXSTC Softail Custom
American Motorcycle Trading Company 

The 2008 Softail Custom combines all the classic areas of Harley-Davidson that motorcycle enthusiasts love. It comes with a 200 mm rear tire and a bobtail fender and the 1584cc twin-cam engine in its second year of reinvention. It has an air-cooled engine that utilizes two valves per cylinder with pushrod operation.

The classic look of a high-hand handlebar cruiser, along with its classic features, makes the Softail Custom a favorite among Harley fans. This bike is a Harley classic, and it’s worth every cent. According to J.D Power, the bike sells in good condition for around $7,000.

10 One Of The Best: 2006 Harley-Davidson VRSCE2 V-Rod – $8,620

2006 Harley-Davidson V-Rod VRSCE2
Chopper Exchange

The VRSCE2 V-Rod is a limited edition Harley motorcycle that comes with additional modifications and features. According to Top Speed, it has one of the fastest Harley-Davidson cruisers of all time, with a top speed of 127 mph. Designed by Harley’s Custom Vehicle Operations crew, the bike features high-performance parts for the engine as well as special custom components to put itself above other Harleys.

The team installed a liquid-cooled, DOHC Revolution engine on the VRSCE2 V-Rod, an engine that has been continually improved throughout the years. The VRSCE2 V-Rod appeared in the top-10 of all time for Harley-Davidsons by Money Inc.

9 One Of The Best: 2009 Harley-Davidson FXSTB Night Train – $10,245

2009 Harley-Davidson FXSTB Night Train
Clean Harleys

With a 1,584cc twin-cam engine that’s proven to last, the 2009 Night Train is a durable bike with style. The bike is best for street cruising and also comes with a six-speed transmission. According to Top Speed, the bike is perfect for younger riders. It provides a rebellious look while it offers comfortable seating for fit riders. The FXSTB is not a fast bike, but has multiple customization options for owners to explore.

8 One Of The Best: 2012 Harley-Davidson CVO Softail Convertible – $15,495

2012 Harley-Davidson CVO Softail Convertible

Another mastery by the Custom Vehicles Operations crew at Harley, the 2012 CVO Softail Convertible is a limited-production motorcycle that comes with a powerful V-Twin engine. Every feature on this Harley is what makes the company a fan favorite. This legend is perfect for customization by riders, which makes it coveted by every motorcycle enthusiast. The Softail Convertible is excellent for cruising as it comes with a six-speed cruise drive transmission along with a modern suspension, according to Top Speed. Owners can customize this bike to ride in two-up cruising, all-day touring, or solo cruising.

7 One Of The Best: 2007 Harley-Davidson XL1200N Sportster Nightster – $9,000

2007 Harley-Davidson XL1200N Sportster Nightster
American Motorcycle Trading Company 

The Sportster Nightster is one of the best Harley bikes ever made and includes all the rugged features of the legendary motorcycle company. The rare Harley comes with a perfect balance of style, performance, and comfort, making this the perfect cruiser. Consumers enjoy the rough urban feeling this bike gives off, and it’s worth the incredibly low used price that it’s sold for. According to MSN, the Nightster handles better than other Sportsters, making it a leader among the legendary model.

6 One Of The Best: 1983 Harley-Davidson XR-1000 – $9,000

1983 Harley-Davidson XR-1000
Mecum Auctions

The XR-1000 was Harley’s bounce back after a horrible streak of bikes released under AMF ownership. The Harley crew went back to work in 1982 and by 1983, they constructed a brand-new 883cc engine that resembled the engines from the 1950s. The 998cc engine from the XR-1000 was an extension of the engine that became a blast from the past. The bike was special in that it was years in the making. The idea for a Sportster XR was sat upon for a while. According to Low Brow Customs, Willie G. Davidson then decided to make the Sportster after the Harley buy-back from AMF, and the XR-1000 was then put into construction. The result was one of the best classic motorcycles you can buy right now.

5 One Of The Best: 2009 Harley-Davidson FLHT Electra Glide – $8,700

2009 Harley-Davidson FLHT Electra Glide
Great South Harley-Davidson 

The 2009 Electra Glide was a Harley built for touring. The Electra Glide had an 80 out of 100 ranking on Bikez, showing how good it was. It has a 1584cc V-Twin engine and a gas tank that carries six gallons of gas, making the bike capable of traveling for long distances. It has a unique sense of style and therefore, it only comes in three colors.

4 One Of The Best: 2007 Harley-Davidson VRSCDX Night Rod Special – $6,570

2007 Harley-Davidson VRSCDX Night Rod Special
Northwest Harley Blog 

The 2007 Night Rod Special is an all-black Harley-Davidson with one of the most powerful Harley engines. With 120 horsepower, the Night Rod Special cements itself as one of the most powerful cruisers. With a low seat and drag-style handlebars, this motorcycle makes for a comfortable ride. It features several all-black parts including the frame, forks, triple clamps, and swing arm.

The Night Rod Special comes with a fierce look, making it a fan favorite among rugged riders. It delivers on the road, as well, with a five-gallon fuel tank and 80 lb-ft of torque, according to Top Speed. This bike is one of the best ever made by Harley.

3 One Of The Worst: 2015 Harley-Davidson Street 500 – $5,000

Harley-Davidson Street 500 outside a building

Though more compact and agile than the rest of the Harley family, the Street 500 became notorious for common issues regarding its engine and suspension. There have even been instances where the bike fell apart mid-cruise. Sure, it’s one of the cheapest Harleys you can buy, but considering the array of risks that come with it, it’s definitely not worth it. We strongly advise cautious and careful inspection if you’re still interested in spending the average asking price of $5,000 on a used one.

2 One Of The Worst: 1981 Harley-Davidson Sportster – $5,645

1981 Harley-Davidson Sportster
 Mecum Auctions

The 1981 Harley-Davidson Sportster was not only one of the worst Harleys ever made, but one of the worst handling bikes ever made by any company. To be fair, 1981 was a bad year for Harley due to their awful business deal with AMF. Harley struggled to produce effective bikes during those dark years and released the Sportster during the turmoil. The Sportster was eventually reinvented after their split with AMF, but it’s best to avoid the 1981 model year.

1 One Of The Worst: Harley-Davidson LiveWire Electric Motorcycle – $25,000

Harley-Davidson Livewire

The electric LiveWire by Harley-Davidson almost became one of the best electric motorcycles. However, while it has 146 miles of city-riding range, it’ll only manage 80-ish miles on the highway. Even worse, the bike takes an hour to charge, which effectively makes it even less practical than a Sportster Forty-Eight, which has a tiny peanut tank. The LiveWire is also priced far too expensive at $27,000.

Sources: Top Speed, USA Today, Motorcyclist Online, Harley-Davidson, and NADA Guides