You don't need $30,000 to get a badass Harley. Here are 7 used models under $20,000 that still deliver serious performance and style.
1. Used Street Glide (2019-2021) – $18,500-$20,000
The Street Glide is Harley's best-selling touring bike for a reason. Used 2019-2021 models with 10,000-20,000 miles typically sell for $18,500-$20,000. You get:
- Milwaukee-Eight 107 engine (111 ft-lb torque)
- Batwing fairing for wind protection
- Premium audio system
- Full touring capability
These bikes are proven reliable, handle great, and look badass. A 2020 Street Glide with 15,000 miles is still a solid bike that'll give you years of trouble-free riding. The Milwaukee-Eight engine is bulletproof, and these bikes hold their value well.
2. Used Road Glide (2019-2021) – $19,000-$20,500
The Road Glide's frame-mounted sharknose fairing gives it better aerodynamics and handling than the Street Glide. Used 2019-2021 models go for $19,000-$20,500. You get:
- Same Milwaukee-Eight 107 power
- Superior wind management
- Better handling at speed
- Distinctive aggressive styling
Road Glides are usually a bit more expensive than Street Glides, but the difference is worth it if you do a lot of highway riding. The frame-mounted fairing makes a real difference in crosswinds and high-speed stability.
3. Used Fat Boy (2020-2022) – $17,500-$19,500
The Fat Boy is an icon. Those solid-disc wheels, that muscular stance – it's unmistakable. Used 2020-2022 models with low miles go for $17,500-$19,500. You get:
- Milwaukee-Eight 107 or 114
- Iconic solid-disc wheels
- Classic cruiser styling
- Serious presence
Fat Boys hold their value because they're so distinctive. A clean 2021 Fat Boy with 8,000 miles is a great buy at $18,500. These bikes turn heads everywhere they go.
4. Used Heritage Classic (2020-2022) – $18,000-$20,000
The Heritage Classic gives you that authentic vintage look with modern reliability. Used 2020-2022 models sell for $18,000-$20,000. You get:
- Milwaukee-Eight 107
- Classic paint and chrome
- Detachable windshield
- Comfortable touring capability
Heritage Classics are perfect if you want that retro look but need modern reliability. A 2021 Heritage Classic with 10,000 miles is a solid buy at $19,000. These bikes look like they came from the '50s but ride like modern bikes.
5. Used Low Rider S (2021-2022) – $19,500-$20,000
The Low Rider S is Harley's sport cruiser. Used 2021-2022 models go for $19,500-$20,000. You get:
- Milwaukee-Eight 117 (biggest engine in the lineup)
- Forward-mounted foot controls
- Aggressive sporty styling
- Serious performance
Low Rider S models are hard to find under $20,000, but they're worth it if you want performance. A 2021 Low Rider S with 12,000 miles at $19,999 is a great deal. These bikes are fast, handle well, and look aggressive.
Browse used Low Rider S models
6. Used Breakout (2020-2022) – $18,000-$19,500
The Breakout is Harley's power cruiser – wide rear tire, slammed stance, serious attitude. Used 2020-2022 models sell for $18,000-$19,500. You get:
- Milwaukee-Eight 114
- 240mm wide rear tire
- Slammed suspension
- Power cruiser styling
Breakouts are for riders who want to make a statement. A 2021 Breakout with 9,000 miles at $18,500 is a solid buy. These bikes look mean and ride aggressive.
7. Used Softail Standard (2021-2023) – $15,000-$18,000
The Softail Standard is the foundation of Harley's cruiser lineup. Used 2021-2023 models go for $15,000-$18,000. You get:
- Milwaukee-Eight 107
- Clean minimalist design
- Hidden rear suspension
- Blank canvas for customization
Softail Standards are the most affordable way into a Milwaukee-Eight bike. A 2022 Softail Standard with 7,000 miles at $16,500 is a great entry point. These bikes are reliable, customizable, and affordable.
What to Look For
When you're shopping for a used Harley under $20,000, focus on:
- Mileage – Under 20,000 miles is ideal, but well-maintained bikes with 30,000+ miles can still be good
- Service history – Full service records are worth more than low miles
- Condition – Check for frame damage, engine issues, electrical problems
- Upgrades – Stage 1 kits, premium audio, custom paint add value
The Bottom Line
You don't need $30,000 to get a great Harley. These 7 models all deliver serious performance and style for under $20,000. Focus on condition and service history, not just price.
Ready to find your used Harley under $20,000? Browse my complete inventory or text me at 414-439-6211 to see what I've got. I'll give you honest pricing and get that bike shipped to your door for $499.
