Used 2021 Jeep Cherokee for Sale nearNewmarket, ON

Summary

• With 100 currently listed for sale near Newmarket, ON and an average price of $22,482.00 CAD, 32.0% of 2021 Jeep Cherokees for sale on CarGurus are rated as good or great deals.

• Favourably reviewed: Owners rated the 2021 Jeep Cherokee 4.8 / 5 stars.

• 100.0% of 2021 Cherokee models on CarGurus are accident free.

Why it stands out

The 2021 Jeep Cherokee stands out as a compact SUV that blends everyday usability with genuine Jeep character. By this point in the model’s life, it had moved well beyond the old, boxy Cherokee formula and into a softer crossover shape, but it still offered the kind of all-weather traction and adventure appeal that helped make the nameplate familiar to buyers. It also remained a strong value proposition in the used market, with the broader third-generation range described as ranging from $6,000 to $40,000.

What makes the 2021 model especially distinctive is how much equipment it had accumulated by then. The 2021 Cherokee added more standard convenience features to each trim, including heated front seats and rain-sensing wipers on the base Sport. That year also sat within a generation that had already gained a 7-inch touchscreen as standard, along with Apple CarPlay and Android Auto, which helped modernise the cabin. Buyers looking for capability could still find the Cherokee appealing because Jeep’s four-wheel drive capability remained one of its core strengths, and the Trailhawk continued to be the version most closely associated with off-road use.

At the same time, the 2021 Cherokee was not without compromises. The generation was known for poor efficiency and some bad engines through the years, and early models in particular had major transmission issues. Even so, for shoppers who wanted a used SUV with good styling, useful technology, and a reputation for capability, the 2021 Jeep Cherokee offered a balanced mix of practicality and Jeep identity.

Other model years to consider

• 2018 Jeep Cherokee

  • Average price: $13,829.00 CAD
  • Good/great deal percentage: 32.7%
  • User rating: 4.8 / 5
  • Total listings: 104

• 2020 Jeep Cherokee

  • Average price: $20,041.00 CAD
  • Good/great deal percentage: 29.5%
  • User rating: 4.77 / 5
  • Total listings: 122

• 2019 Jeep Cherokee

  • Average price: $15,920.00 CAD
  • Good/great deal percentage: 29.4%
  • User rating: 4.67 / 5
  • Total listings: 109

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