Used Jeep Gladiator for Sale near South Milwaukee, WI

Summary

• With 6,227 currently listed for sale on CarGurus and an average price of $31,692.20, 35.1% 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.
• 84.9% of 2021 Gladiator models on CarGurus are accident free.
• The 2021 Jeep Gladiator introduced a powerful 3.0-liter EcoDiesel V6 engine option, enhancing fuel efficiency and towing capacity for adventurous drivers.

Why it stands out

The Jeep Gladiator distinguishes itself in the midsize pickup market with its unique blend of open-air driving and rugged off-road capability, drawing heavily from its Wrangler heritage. It offers removable doors and a folding windshield for an unparalleled outdoor experience, along with an extensive list of aftermarket accessories for customization. With impressive towing capacity and specialized features like locking differentials, the Gladiator is designed for those who seek adventure both on and off the beaten path.

Other model years to consider

The 2020 Jeep Gladiator emerges as a highly viable option, offering a strong combination of value at an average price of $29,662.08 and an impressive user rating of 4.7/5, indicating high user satisfaction. The 2023 model also stands out with its excellent user rating of 4.8/5 and competitive pricing, making it a compelling choice for those looking for a newer vehicle with great features, while still maintaining favorable market positioning with 35% good/great deals available. Meanwhile, the 2022 model presents moderate suitability due to its slightly lower user rating and higher average price relative to the value offered by the other years.

Model years to approach with caution

When considering the Jeep Gladiator, buyers should carefully evaluate the model years based on financial aspects, quality metrics, and availability constraints. The 2024 model year stands out as the most suitable option, with a relatively lower average price compared to 2025, but both years show a significant percentage of listings classified as not good/great deals. The 2026 model appears moderately suitable due to its high percentage of not good/great deals, suggesting that potential buyers should conduct thorough research to ensure they are making an informed purchase decision.

These recommendations are based on CarGurus' proprietary market data from December 17, 2025, CarGurus experts' opinions, and generative AI.