Used 2020 Jeep Grand Cherokee for Sale near Winnipeg, MB
58 results
CarGurus Analysis:
2020 Jeep Grand Cherokee
With 59 currently listed for sale near Winnipeg, MB and an average price of $23,070.00 CAD, 39.0% of 2020 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2020 Jeep Grand Cherokee 4.58 / 5 stars.
100.0% of 2020 Grand Cherokee models on CarGurus are accident free.
The 2020 Jeep Grand Cherokee features a luxurious interior and a robust array of powerful engines, including a V8 option, making it perfect for both on-road and off-road adventures.
CarGurus Analysis: 2020 Jeep Grand Cherokee
overall
Summary
With 59 currently listed for sale near Winnipeg, MB and an average price of $23,070.00 CAD, 39.0% of 2020 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2020 Jeep Grand Cherokee 4.58 / 5 stars.
100.0% of 2020 Grand Cherokee models on CarGurus are accident free.
The 2020 Jeep Grand Cherokee features a luxurious interior and a robust array of powerful engines, including a V8 option, making it perfect for both on-road and off-road adventures.
Why it stands out
The 2020 Jeep Grand Cherokee remains a strong contender in the midsize SUV segment, combining style, performance, and capability. While it enters its tenth model year without a significant redesign, its classic Jeep styling with a 7-slot grille and rugged allure continues to attract a diverse range of buyers. The Grand Cherokee offers multiple engine choices, including a powerful V8, and is equipped with a sophisticated four-wheel-drive system, enhancing its prowess on various terrains. Though the ride quality can be affected by its larger wheels and suspension setup, many owners appreciate its blend of comfort and performance. Notably, advanced safety features like blind-spot monitoring and rear cross-traffic alert ensure a secure driving experience. However, potential buyers should consider that the seating comfort may not accommodate taller individuals, and there are concerns regarding the cost-effectiveness compared to competitor SUVs. Overall, the Grand Cherokee's well-rounded talents make it an appealing option for both off-road enthusiasts and everyday drivers.
Other model years to consider
- Average price: $37,989.00 CAD
- Good/great deal percentage: 36.4%
- User rating: 4.86 / 5
- Total listings: 66
- Average price: $43,623.00 CAD
- Good/great deal percentage: 27.8%
- User rating: 5 / 5
- Total listings: 54
- Average price: $47,879.00 CAD
- Good/great deal percentage: 27.6%
- User rating: 5 / 5
- Total listings: 58
This analysis is based on CarGurus' proprietary market data from June 24, 2026, CarGurus experts' opinions, and generative AI.
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Anonymous
Reviewed a 2020 Jeep Limited 4WD on Jul 30, 2025
I love all the features on this car. I think it was a great value. Its the JGC X, which has a little more options than regular. Love the slate blue color.
Samuel M
Reviewed a 2020 Jeep Grand Cherokee on Dec 19, 2025
2nd Jeep Cherokee we have bought and they are great vehicles and very reliable.
Tristan H
Reviewed a 2020 Jeep Grand Cherokee on Jan 10, 2025
Great car loads of features! Amazing platform plenty of power and capability.
Dan H
Reviewed a 2020 Jeep Grand Cherokee on Jun 7, 2022
My favorite Grand Cherokee Summit is the one with the 5.7 HEMI V8 with 4x4 off road capability plus the power of the wonderful V8 HEMI. all in one marvelous package called Summit. The ultimate SUV. The jeep is the only capable SUV I Trust.
2020 Jeep Grand Cherokee Trims
| Trim type | MSRP |
|---|---|
| Trailhawk 4WD | $45,155 |
| Overland 4WD | $49,695 |
| SRT 4WD | $68,895 |
| Summit 4WD | $55,495 |
| Limited X 4WD | $47,050 |
| Laredo 4WD | $34,450 |
| Limited 4WD | $41,955 |
| Altitude 4WD | $40,540 |
2020 Jeep Grand Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Jeep Grand Cherokee prices has changed over time.
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