Used Jeep Cherokee for Sale near Windsor, WI
CarGurus recommends the 2019 Jeep Cherokee
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.
4.4 Overall rating
(1,108 reviews)Customers say
The Jeep Cherokee has long been celebrated for its rugged reliability, impressive off-road capabilities, and overall durability. Owners tend to praise its powerful engines, spacious interiors, and user-friendly features across various models. Many drivers also appreciate the comfortable ride and the great value it offers. However, some common complaints include inconsistent performance, fuel economy concerns, and occasional reliability issues, particularly with older models. In essence, the Cherokee stands out as a dependable choice for those who enjoy adventure and need a versatile vehicle, though it may not always deliver on efficiency and peak performance.
AI generated from the text of customer reviews.
What people say
My husband and I absolutely enjoy this new car of ours. This is the vehicle we want and need. The features are perfect and everything works great, though we had to replace the brakes, spark plugs , and a few other things. The vehicle is in excellent condition and still looks new. The interior is beautiful. It’s the best vehicle for all of the driving that we do.
The 2021 Jeep Cherokee is a versatile compact SUV that excels in off-road performance, particularly in the Trailhawk trim, thanks to its advanced 4x4 system and terrain management features.
The cars features are great it rides nice and had a one stop shop for everything we wanted in a family vehicle couldnt be happier
The vehicle is very capable on and off road. Plenty of power to get up to speed on the highway, pass someone, and 4500lb towing capacity. Also it is the only trailhawk in the lineup to have a true rear locker.
The car’s features are awesome, all this at a great deal
Jeep Cherokee FAQs
How much does the Jeep Cherokee cost in Windsor, WI?
The average Jeep Cherokee costs about $15,572.75. The average price has decreased by -9.1% since last year. The 588 for sale near Windsor, WI on CarGurus, range from $3,828 to $28,364 in price.
How many Jeep Cherokee vehicles in Windsor, WI have no reported accidents or damage?
538 out of 588 for sale near Windsor, WI have no reported accidents or damage.
What fuel types are available?
Gasoline engines are available.
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Used Jeep Cherokee for Sale Under $40,000 Near Windsor
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