Summary

• With 368 currently listed for sale near Milwaukee, WI and an average price of $30,779.00, 37.8% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals.

• Favorably reviewed: Owners rated the 2021 Jeep Gladiator 5 / 5 stars and CarGurus experts gave it a 7.17 / 10.

• 100.0% of 2021 Gladiator models on CarGurus are accident free.

Why it stands out

The 2021 Jeep Gladiator stands out because it blends pickup-truck utility with the Wrangler-based personality that makes it feel unlike other midsize trucks. Its removable top and doors, along with an extensive list of aftermarket accessories, give it a level of personalization and adventure appeal that is hard to match. Jeep also added a turbo-diesel engine option for the 2021 model year, and the truck could be had with available full-time four-wheel drive, fresh special-edition models, and free scheduled maintenance.

That character comes with tradeoffs, and the Gladiator does not hide them. The test-drive data points to poor fuel economy, poor ride quality, and poor handling, so buyers should expect a truck that prioritizes style and fun over refinement. Even so, it remains appealing for shoppers who want a midsize pickup that is stylish, offers a manual transmission, and is genuinely fun to drive.

Other model years to consider

• 2020 Jeep Gladiator

  • Average price: $27,603.00
  • Good/great deal percentage: 33.2%
  • User rating: 4.83 / 5
  • Total listings: 262

• 2022 Jeep Gladiator

  • Average price: $32,036.00
  • Good/great deal percentage: 36.1%
  • User rating: 4.2 / 5
  • Total listings: 377

• 2023 Jeep Gladiator

  • Average price: $34,617.00
  • Good/great deal percentage: 33.8%
  • User rating: 4.82 / 5
  • Total listings: 275

This analysis is based on CarGurus' proprietary market data from August 11, 2026, CarGurus experts' opinions, and generative AI.