Used Jeep Cherokee for Sale near Pittsfield, MA
CarGurus recommends the 2019 Jeep Cherokee
Summary
- With 4,947 currently listed for sale on CarGurus and an average price of $15,815.40, 33.2% 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% of 2019 Cherokee models on CarGurus are accident free.
- The 2019 Jeep Cherokee excelled with its off-road capability, featuring advanced four-wheel-drive systems for tackling diverse terrains with confidence.
Why it stands out
The Jeep Cherokee stands out in the compact crossover market due to its exceptional off-road capabilities, particularly in the Trailhawk trim, which rivals even the legendary Jeep Wrangler. Its advanced 4-wheel-drive and terrain-management systems offer both rugged performance and enhanced on-road comfort, making it a versatile option for those who seek adventure without sacrificing daily usability. Additionally, with a more affordable price point than the Grand Cherokee, it presents a compelling choice for Jeep enthusiasts looking for an accessible SUV that doesn't compromise on capability.
Other model years to consider
The 2020 Jeep Cherokee stands out as a great option with a competitive average price of $17,818.45 and an impressive user rating of 4.6 out of 5, alongside a solid 34% of listings categorized as good or great deals. The 2018 model also offers significant value at an average price of $13,934.89 and a user rating of 4.4 out of 5, making it another moderately suitable alternative with a similar proportion of good deals available. Additionally, the 2015 model presents an appealing option for budget-conscious buyers, featuring an average price of just $10,008.02 and a respectable user rating of 4.5 out of 5, with about 32% classified as good or great deals.
Model years to approach with caution
In analyzing the Jeep Cherokee model years, several factors come into play. The 1998 and 2000 models stand out as the most suitable options, both receiving strong user ratings and typically commanding reasonable prices in the marketplace. On the other hand, while the 2014 model is available at a lower average price, it shows a decline in customer satisfaction, with many users rating it below previous generations. Overall, potential buyers should consider these aspects carefully to make an informed decision that aligns with their preferences for value and satisfaction.
These recommendations are based on CarGurus' proprietary market data from December 3, 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 Pittsfield, MA?
The average Jeep Cherokee costs about $16,404.75. The average price has decreased by -6% since last year. The 685 for sale near Pittsfield, MA on CarGurus, range from $3,995 to $33,797 in price.
How many Jeep Cherokee vehicles in Pittsfield, MA have no reported accidents or damage?
620 out of 685 for sale near Pittsfield, MA have no reported accidents or damage.
What fuel types are available?
Gasoline engines are available.
-
All Used Cars
-
Manual Transmission Cars
-
Luxury Cars
-
Cars with Red Interior
-
Cheap Manual Cars
-
Hybrid Cars
-
Sports Cars
-
Electric SUVs
-
Cheap Trucks
-
Small Cars
-
Third Row SUVs
-
Three Quarter Ton Trucks
-
Lifted Trucks
-
Manual Transmission Trucks
-
Diesel Trucks
-
Hybrid SUVs
-
Dually Trucks
-
One Ton Trucks
-
Cheap SUVs
-
Lifted Ford Trucks
-
4x4 Trucks
-
Work Trucks
-
AWD SUVs
-
Ford Trucks
-
Chevrolet Trucks
-
Toyota Trucks
-
Trucks Under $10,000
-
Cars Under $15,000
-
Sports Cars Under $20,000
-
Trucks Under $20,000
-
Used Sedans for Sale with Low Mileage
-
Used SUVs / Crossovers for Sale with Low Mileage
-
Used Hatchbacks for Sale with Low Mileage
-
Used Convertibles for Sale with Low Mileage
-
Used Vans for Sale with Low Mileage
-
Used Minivans for Sale with Low Mileage
-
Used Pickup Trucks for Sale with Low Mileage
-
Used Coupes for Sale with Low Mileage
-
Used Wagons for Sale with Low Mileage
-
Bertera Dodge Chrysler Jeep Ram
-
Stephens Chrysler Jeep Dodge Ram of Bennington
-
Metro Chrysler Dodge Jeep Ram
-
Bedard Bros Auto Sales
-
Otto Chrysler Dodge Jeep Ram
-
Brattleboro Chrysler Dodge Jeep Ram
-
Lia Chrysler Jeep Dodge Ram
-
Goldstein Chrysler Jeep Dodge Ram
-
Sullivan's Northwest Hills Chrysler Jeep Dodge Ram
-
Orchard CDJR
-
Lia Chrysler Jeep Dodge Ram Northampton
-
Ruge's Automotive