New & Used 2025 Jeep Gladiator for Sale near Chester, CT

## Summary - With 1,169 currently listed for sale and an **average price of $44,274.00**, 33.5% of 2025 Jeep Gladiators for sale on CarGurus are rated as good or great deals. - **96.5% of 2025 Gladiator models on CarGurus are accident free**. - The 2025 Jeep Gladiator is known for its convertible top and removable doors, making it a unique choice among pickup trucks. ## Why it stands out The 2025 Jeep Gladiator distinguishes itself in the midsize pickup truck market through its unique blend of utility and adventure. It offers an open-air driving experience with its convertible top and removable doors, appealing to those who enjoy outdoor adventures. The Gladiator's capability in off-road situations is reinforced by features like four-wheel drive and a robust construction designed to tackle tough terrains. Although it can tow up to 7,700 pounds and carry a payload of 1,725 pounds, buyers should be aware that these figures primarily apply to the base Sport trim, and more expensive variants may not excel in towing and payload capacity. In terms of driving dynamics, the Gladiator provides a distinctively rugged experience, allowing for a fun and engaging drive, especially off-road. However, it does come with certain drawbacks, such as less competitive towing capabilities compared to rivals and relatively poor fuel economy. The Gladiator's safety features are also less comprehensive than some competitors, placing a higher emphasis on optional features rather than including them as standard. Overall, the Gladiator is ideal for those who prioritize unique styling and off-road capability over maximum towing power. ## Other model years to consider - **[2023 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2023-Jeep-Gladiator-c32473)** - Average price: $33,775.00 - Good/great deal percentage: 32.0% - User rating: 4.84 / 5 - Total listings: 3,531 - **[2021 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2021-Jeep-Gladiator-c30873)** - Average price: $31,019.00 - Good/great deal percentage: 33.2% - User rating: 4.8 / 5 - Total listings: 4,773 - **[2020 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2020-Jeep-Gladiator-c28934)** - Average price: $28,503.00 - Good/great deal percentage: 33.3% - User rating: 4.72 / 5 - Total listings: 3,278 This analysis is based on CarGurus' proprietary market data from March 20, 2026, CarGurus experts' opinions, and generative AI.