New & Used 2025 Jeep Gladiator for Sale near Windsor, VA

## Summary - With 1,209 currently listed for sale on CarGurus and an **average price of $44,506.00**, 34.2% of 2025 Jeep Gladiators for sale on CarGurus are rated as good or great deals. - **Accident-free percentage:** 98.1%. - The 2025 Jeep Gladiator stands out as a unique blend of a pickup truck, convertible, and off-roader, offering intriguing options for those valuing open-air driving and rugged capability. ## Why it stands out The 2025 Jeep Gladiator distinguishes itself with its convertible functionality and off-road prowess, characteristics that set it apart in the midsize pickup segment. This year, most notably, the model has shifted away from a manual transmission, while introducing several special edition trims and vibrant new color options. The Gladiator is built on an extended truck frame that enhances its towing capacity, which can reach up to 7,700 pounds in its base Sport trim, perfect for versatility whether you're hauling gear or navigating the wilderness. Yet, the model does have its limits; for users focused primarily on heavy-duty towing and payload demands, alternatives might offer better specifications. Additionally, while the cabin features improved legroom and comfort levels compared to previous models, the interior quality may not feel commensurate with its price. Overall, the 2025 Gladiator is ideal for buyers seeking adventure without foregoing the practicality of a truck. ## Other model years to consider - **[2023 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2023-Jeep-Gladiator-c32473)** - Average price: $33,294.00 - Good/great deal percentage: 32.5% - User rating: 4.84 / 5 - Total listings: 4,014 - **[2022 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2022-Jeep-Gladiator-c32007)** - Average price: $32,159.00 - Good/great deal percentage: 32.3% - User rating: 4.4 / 5 - Total listings: 5,435 - **[2021 Jeep Gladiator](https://www.cargurus.com/Cars/l-Used-2021-Jeep-Gladiator-c30873)** - Average price: $30,766.00 - Good/great deal percentage: 33.2% - User rating: 4.8 / 5 - Total listings: 5,500 This analysis is based on CarGurus' proprietary market data from February 9, 2026, CarGurus experts' opinions, and generative AI.