Used 2020 Jeep Cherokee for Sale nearOshawa, ON

Summary

• With 115 currently listed for sale near Oshawa, ON and an average price of $19,001.00 CAD, 27.8% of 2020 Jeep Cherokees for sale on CarGurus are rated as good or great deals.

• Favourably reviewed: Owners rated the 2020 Jeep Cherokee 4.77 / 5 stars.

• 100.0% of 2020 Cherokee models on CarGurus are accident free.

Why it stands out

The 2020 Jeep Cherokee stands out as a compact SUV that blends Jeep’s familiar all-weather capability with a more crossover-like shape and a long list of available equipment. By this point in the third generation, it had already moved far from the boxy, old-school Cherokee formula, yet it still offered features such as Selec-Terrain, available low-range hardware on some trims, and the Trailhawk’s more rugged setup for buyers who wanted extra off-road credibility. It also remained distinctive for its styling, which had been refreshed for 2019 with a conventional one-piece headlamp design, a new hood, bumper, fog lamps, and taillamps.

For 2020, Jeep added new wheels and colours across various trims, including Sangria and Spitfire Orange, and Alexa was added to Uconnect 8.4 systems with navigation. The Cherokee also carried over a practical interior update from the previous refresh, including a 7-inch touchscreen as standard, Apple CarPlay, Android Auto, and a revised centre console with a larger pocket for phones. Cargo space had increased to 764 litres, which helps explain why the model appealed to buyers looking for a usable daily driver with a bit of extra versatility.

There are trade-offs, though. The buying guide notes poor efficiency and some bad engines through the years, and the third generation in particular had major transmission issues in its early years. Even so, the 2020 Cherokee could still make sense for shoppers who value Jeep’s four-wheel drive capability, good styling, and strong value more than outright refinement.

Other model years to consider

• 2018 Jeep Cherokee

  • Average price: $13,705.00 CAD
  • Good/great deal percentage: 31.3%
  • User rating: 4.8 / 5
  • Total listings: 99

• 2019 Jeep Cherokee

  • Average price: $15,818.00 CAD
  • Good/great deal percentage: 28.2%
  • User rating: 4.67 / 5
  • Total listings: 103

• 2022 Jeep Cherokee

  • Average price: $26,711.00 CAD
  • Good/great deal percentage: 32.5%
  • User rating: 5 / 5
  • Total listings: 83

This analysis is based on CarGurus' proprietary market data from September 2, 2026, CarGurus experts' opinions, and generative AI.