Used Jeep Cherokee for Sale near Upperville, VA

Summary

• With 4,938 currently listed for sale on CarGurus and an average price of $15,645.90, 33.5% of 2019 Jeep Cherokees for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2019 Jeep Cherokee 4.5 / 5 stars and CarGurus experts gave it an 8 / 10.
• 68.1% of 2019 Cherokee models on CarGurus are accident free.
• The 2019 Jeep Cherokee featured an available V6 engine option, delivering a robust 271 horsepower for confident highway merging and towing capabilities.

Why it stands out

The Jeep Cherokee stands out in the compact crossover segment with its exceptional off-road capability, particularly in the Trailhawk trim, which rivals the legendary Jeep Wrangler. It features advanced 4-wheel-drive and terrain-management systems, making it an ideal choice for adventurous drivers who seek both rugged performance and affordability compared to larger models like the Grand Cherokee. Redesigned for 2019, the Cherokee combines modern aesthetics with practicality, appealing to both Jeep enthusiasts and compact SUV buyers alike.

Other model years to consider

When considering the Jeep Cherokee, the 2022 model year stands out as a highly favorable option with an impressive user rating of 4.8/5 and a significant percentage of good/great deals at 35%. The 2020 model also presents solid value, featuring a strong user satisfaction rating of 4.6/5 and an average price that remains competitive in the market. For those looking for budget-friendly alternatives, the 2018 model offers a commendable balance of affordability and satisfaction with a user rating of 4.4/5, making it a moderately suitable choice for buyers seeking value without sacrificing quality.

Model years to approach with caution

The 2017 Jeep Cherokee faces challenges in market positioning due to its average price of $12,132.60 coupled with a significant percentage of users (68%) indicating it is not a good or great deal, suggesting potential value concerns. User feedback has dropped to a 3.8/5 rating for the 2014 model year, indicating that more recent models may not meet user expectations as effectively as earlier versions. In contrast, older model years such as those from the late 1990s and early 2000s show consistently high user ratings, reflecting a more favorable perception of quality and value among consumers during those periods.

These recommendations are based on CarGurus' proprietary market data from December 17, 2025, CarGurus experts' opinions, and generative AI.