Used Jeep Wrangler for Sale near Winchester, VA

Summary

• With 9,698 currently listed for sale on CarGurus and an average price of $30,847.50, 33.5% of 2021 Jeep Wranglers for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2021 Jeep Wrangler 4.7 / 5 stars and CarGurus experts gave it an 7.7 / 10.
• 83.7% of 2021 Wrangler models on CarGurus are accident free.
• The 2021 Jeep Wrangler introduced the Rubicon 392 trim, featuring a powerful Hemi V8 engine with 470 horsepower for unmatched off-road capability.

Why it stands out

The Jeep Wrangler stands out as an enduring symbol of ruggedness and versatility, seamlessly blending its storied history with modern advancements. It retains classic features like removable doors and a fold-flat windshield while introducing contemporary options such as the 4xe plug-in hybrid and the powerful Hemi V8 engine exclusive to its four-door model. This balance of tradition and innovation not only appeals to off-road enthusiasts but also ensures the Wrangler remains relevant in an ever-evolving automotive landscape.

Other model years to consider

The Jeep Wrangler model years 2018, 2019, and 2020 offer solid value for buyers looking for an affordable combination of quality and reliability. With average prices significantly lower than newer models, these years boast user ratings consistently above 4.4 out of 5 and a high percentage of good or great deals available in the marketplace. Additionally, their ample inventory means that potential buyers have a wide selection to choose from while still enjoying the classic Jeep performance and style.

Model years to approach with caution

Considering the Jeep Wrangler model years available, several patterns emerge regarding market positioning and user feedback. The 2009, 2010, and 2011 models display similar user ratings around 4.3 to 4.0 but are also characterized by a significant percentage of listings that are not perceived as good deals, suggesting potential pricing challenges in these years. Conversely, older models from the 1990s consistently receive high user ratings of around 4.4 to 4.6, indicating strong satisfaction among owners despite limited availability in today's market; however, they also face a high proportion of listings considered not good deals, which may reflect their rarity or collector status rather than everyday usability.

These recommendations are based on CarGurus' proprietary market data from December 3, 2025, CarGurus experts' opinions, and generative AI.