Used 2020 Jeep Gladiator for Sale near Winnipeg, MB

## Summary - With 161 currently listed for sale and an **average price of $35,417.00 CAD**, 30.4% 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**. - The 2020 Jeep Gladiator marks the brand’s return to the pickup truck market, boasting a unique open-air driving experience with removable doors and a foldable windshield, alongside solid off-road capabilities. ## Why it stands out The 2020 Jeep Gladiator combines the rugged off-road heritage of the Jeep brand with the utility of a midsize truck. Sharing its foundation with the Jeep Wrangler, the Gladiator stands out with features like removable doors and a fold-down windshield, allowing for a distinctive open-air driving experience not commonly found in the truck segment. It carries a Trail Rated badge highlighting its off-road performance, reinforced by heavy-duty options such as locking differentials and sway bar disconnects. While it faces critiques for a noisy ride at highway speeds and a somewhat cramped interior, its strong resale value and overall versatility appeal to adventure seekers and lifestyle-oriented buyers alike. The Gladiator offers a unique blend of off-road capability, customization options, and a solid towing capacity of up to 3,460 kilograms, making it an enticing option for those looking to tackle both rugged terrains and everyday tasks. ## Other model years to consider - **[2021 Jeep Gladiator](https://www.cargurus.ca/Cars/l-Used-2021-Jeep-Gladiator-c30873)** - Average price: $39,830.00 CAD - Good/great deal percentage: 30.9% - User rating: 5 / 5 - Total listings: 223 - **[2022 Jeep Gladiator](https://www.cargurus.ca/Cars/l-Used-2022-Jeep-Gladiator-c32007)** - Average price: $42,986.00 CAD - Good/great deal percentage: 31.3% - User rating: 4.2 / 5 - Total listings: 268 - **[2023 Jeep Gladiator](https://www.cargurus.ca/Cars/l-Used-2023-Jeep-Gladiator-c32473)** - Average price: $47,887.00 CAD - Good/great deal percentage: 32.5% - User rating: 4.82 / 5 - Total listings: 194 This analysis is based on CarGurus' proprietary market data from April 27, 2026, CarGurus experts' opinions, and generative AI.