Harley Softail, which one to Buy?

🏍️ Updated The Softail Index: Why Select Harley-Davidson Models Are Appreciating — and Which Engines to Buy Used

“Most motorcycles depreciate the moment they leave the lot — except when they don’t.”

1. What

Makes a Softail Special?

Since its launch in 1984, the Softail has defined the modern cruiser:

· ✅ Hidden rear mono-shock (looks like a hardtail, rides like a dream)

· ✅ Big V-twin torque

· ✅ Iconic design that never goes out of style

· ✅ Hugely customizable — perfect for purists and builders alike

2. Why Are Softails Gaining Value?

🏭 Limited Supply (2018–2021)

Harley slashed production to reposition itself as a premium brand. Result? Used inventory dried up.

🦠 Pandemic Demand Surge

COVID created a new wave of riders craving freedom and open roads — and they went looking for Harleys.

👴 Boomer Nostalgia

Financially comfortable retirees are hunting down 1990s and 2000s models they once couldn’t afford.

🔧 Custom Culture

Stock bikes are being chopped and rebuilt — so original condition bikes are getting rarer and more desirable.

3. The Best Used Softails to Buy in 2025

· Fat Boy (1990–1999, 2007–2008) — 🔼🔼 — *Terminator 2* bike, iconic disc wheels

· Heritage Softail Classic (2004–2012) — 🔼 — Chrome-laden, bags, tour-ready

· Softail Deluxe (2005–2017) — 🔼 — Whitewalls, low-slung design

· FXST Standard (2001–2006) — 🔼 — A blank canvas for custom builders

· Breakout (CVO) (2013–2017) — 🔼🔼 — Rare, aggressive styling, factory custom

· Cross Bones (FLSTSB) (2008–2011) — 🔼🔼 — Springer fork, blacked-out finish

4. Which Engine Should You Buy Used?

⚙️ Evolution (1984–1999)

· Simple, carbureted, and bulletproof.

· Best for: Collectors, tinkerers

· Look for: FXST or Heritage up to 1999

⚙️ Twin Cam 88 & 96 (1999–2017)

· Smooth with internal counterbalancers.

· Best for: Daily riders, torque lovers

· Look for: 2007 Fat Boy or 2006 Heritage

· Tip: Upgrade cam chain tensioners if not done

⚙️ Twin Cam 103 & 110 (2012–2017)

· EFI, low-maintenance, great 2-up power.

· Best for: Touring and resale value

· Look for: Breakout, Heritage, or CVO models

⚙️ Milwaukee-Eight 107/114 (2018+)

· Modern, efficient, smoothest ride yet.

· Best for: Long-term investment

· Look for: 2018–2020 Slim or Heritage

· Tip: Low miles matter!

5. How to Evaluate a Used Softail

· ✅ Under 10,000 miles is ideal — but full service history matters more

· ✅ Original paint and OEM parts increase value

· ⚠️ Avoid repaints, over-customized bikes, and rebuilt titles

6. Where to Buy

· Private sellers – Better price, flexible

· Harley forums & Facebook groups – Good for enthusiast bikes

· Bring a Trailer / Mecum – Collector-grade units

· Avoid: Craigslist customs, salvage/rebuilt titles, stripped bikes

7. 📈 The Softail Index — Market Price Trends

Fat Boy (90s): $6,200 → $10,800 → $11,700
Cross Bones: $10,500 → $16,900 → $18,000
Softail Deluxe: $9,800 → $12,600 → $13,100
FXST Standard: $7,500 → $11,400 → $12,200

8. Engine Cheat Sheet: Match by Goal

Classic collectible — Evo 1340
Daily rider — Twin Cam 96B
Resale value — Twin Cam 103 / M8 114
Collector investment — CVO Twin Cam 110

🔧 2025 Softail Watchlist

· 2007 Fat Boy 96B — Target $9,500–$10,500

· 2011 Cross Bones — $14,000–$16,000

· 2018 Heritage Classic 114 — Premium if under 5K miles

· Any FXST Standard — In original factory paint

🎬 Final Thoughts

If you're looking for a bike that won’t just *hold* its value — but grow it — Harley Softails are a solid bet.
Inventory is shrinking. Demand is rising. And clean Twin Cam and Evo bikes are getting snapped up by smart buyers.

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By Rafael Benavente