Used Jeep Gladiator for Sale near Chesapeake, VA

Summary

• With 6,122 currently listed for sale on CarGurus and an average price of $31,934.50, 32.6% 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 diesel engine option, enhancing towing capacity and fuel efficiency for adventurous drivers.

Why it stands out

The Jeep Gladiator stands out in the midsize truck market with its unique open-air driving experience, allowing drivers to remove the top and doors for an adventurous ride. Additionally, its exceptional off-road capabilities, highlighted by features like the Trail Rated badge and available locking differentials, make it a compelling choice for outdoor enthusiasts. With options such as a turbo-diesel engine and an extensive range of aftermarket accessories, the Gladiator combines practicality with personalization to cater to diverse lifestyles.

Other model years to consider

The Jeep Gladiator model years 2020 and 2023 present the most suitable options for buyers seeking a blend of value and user satisfaction. The 2020 model, with an average price of approximately $29,893 and a high user rating of 4.7/5, offers significant affordability alongside a solid reputation for performance. Meanwhile, the 2023 model boasts an impressive user rating of 4.8/5 and remains competitively priced at about $33,790, reflecting strong market positioning and user satisfaction.

The 2022 Gladiator is moderately suitable, offering decent value with a user rating of 4.4/5 at an average price of $33,420. While it has a similar percentage of good/great deals as the newer models, it does not stand out in terms of ratings compared to its counterparts. The 2024 model, while featuring updated designs and technology, comes at a higher price point averaging around $40,430 but does not demonstrate significantly improved user satisfaction or expert ratings to justify the cost increase.

Model years to approach with caution

When considering the Jeep Gladiator, buyers should carefully evaluate the 2025 and 2026 model years due to their marketplace dynamics. The average price for the 2025 model is around $46,629.91, which may represent a significant investment given its moderate expert rating of 5.3/10 and a notable 66% of listings categorized as not good/great deals. Meanwhile, the 2026 model shows that a substantial 68% of deals are also viewed as less favorable, indicating that shoppers should prioritize thorough research on pricing and customer satisfaction levels across these years to make informed decisions.

These recommendations are based on CarGurus' proprietary market data from December 9, 2025, CarGurus experts' opinions, and generative AI.