Used 2020 Jeep Gladiator for Sale near Winnipeg, MB

## Summary - With 161 currently listed for sale and an **average price of $35,448.00 CAD**, 29.2% of 2020 Jeep Gladiators for sale on CarGurus are rated as good or great deals. - **Favourably reviewed:** Owners rated the 2020 Jeep Gladiator 4.82 / 5 stars. - **100.0% of 2020 Gladiator models on CarGurus are accident free**. ## Why it stands out The 2020 Jeep Gladiator makes a distinctive statement in the midsize truck market by combining the ruggedness of a Jeep with the utility of a pickup. Notably, it marks Jeep's return to the pickup segment after a long absence, sharing its underpinnings with the popular Wrangler, which enhances its off-road performance. A standout feature is its unique open-air driving experience; both the doors and the windshield can be removed, allowing for an adventurous drive like no other. Additionally, the Gladiator is equipped with a range of features suited for off-road enthusiasts, such as locking differentials and Trail Rated capability for superior handling on challenging terrains. This model has also garnered praise for its versatile cargo area, making it attractive to buyers seeking both style and functionality. However, some users have noted an increase in cabin noise at higher speeds and a feeling of cramped interiors. Overall, the Gladiator appeals to those prioritising an adventurous lifestyle and off-road capability alongside everyday utility. ## Other model years to consider - **[2021 Jeep Gladiator](https://www.cargurus.ca/Cars/l-Used-2021-Jeep-Gladiator-c30873)** - Average price: $40,065.00 CAD - Good/great deal percentage: 29.0% - User rating: 5 / 5 - Total listings: 224 - **[2022 Jeep Gladiator](https://www.cargurus.ca/Cars/l-Used-2022-Jeep-Gladiator-c32007)** - Average price: $43,055.00 CAD - Good/great deal percentage: 28.5% - User rating: 4.2 / 5 - Total listings: 274 - **[2023 Jeep Gladiator](https://www.cargurus.ca/Cars/l-Used-2023-Jeep-Gladiator-c32473)** - Average price: $47,866.00 CAD - Good/great deal percentage: 30.8% - User rating: 4.82 / 5 - Total listings: 195 This analysis is based on CarGurus' proprietary market data from April 20, 2026, CarGurus experts' opinions, and generative AI.