Used Jeep Gladiator for Sale near Milwaukee, WI

Summary

• With 6,057 currently listed for sale on CarGurus and an average price of $32,081.70, 32.2% of 2021 Jeep Gladiators for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2021 Jeep Gladiator 4.8 / 5 stars and CarGurus experts gave it an 7.2 / 10.
• 85% of 2021 Gladiator models on CarGurus are accident free.
• The 2021 Jeep Gladiator introduced a diesel engine option, enhancing fuel economy and towing performance for adventurous drivers.

Why it stands out

The Jeep Gladiator stands out in the midsize pickup segment with its unique combination of off-road capability and open-air driving experience, reminiscent of its Wrangler roots. Features like removable doors and a folding windshield provide an unparalleled sense of adventure, while the availability of heavy-duty components, such as locking differentials and specialized off-road trims, ensure it excels in challenging terrains. Additionally, the Gladiator’s strong towing capacity and diverse range of customization options make it a versatile choice for both work and play.

Other model years to consider

When considering the Jeep Gladiator, the 2020 and 2023 model years stand out as the most suitable options. The 2020 model offers an attractive average price of $29,999.33 along with a strong user rating of 4.7/5, making it a compelling choice for budget-conscious buyers with a good availability of deals at 33%. Meanwhile, the 2023 model boasts an impressive user rating of 4.8/5 and only slightly higher pricing at $33,905.42, also benefiting from consistent deal availability at 33%.

Moderately suitable is the 2022 model year, which has a competitive average price of $33,539.20 but a slightly lower user rating of 4.4/5 and similar deal availability to its predecessors. The newest option, the 2024 model year, while featuring an expert rating of 7.3/10 and good deal availability at 34%, has a significantly higher average price of $40,594.59, making it less appealing compared to earlier models in terms of value for money.

Model years to approach with caution

Based on current marketplace data, the 2025 and 2026 Jeep Gladiator model years should be approached with caution. The 2025 model has an average price of $47,179.47 and an expert rating of 5.3 out of 10, indicating moderate customer satisfaction levels, along with a notable 66% of listings classified as not good or great deals. Similarly, the upcoming 2026 model shows that 70% of available deals are not rated positively, suggesting potential value concerns in the market.

These recommendations are based on CarGurus' proprietary market data from December 3, 2025, CarGurus experts' opinions, and generative AI.