Used 2021 Jeep Grand Cherokee for Sale near Winnipeg, MB
62 results
CarGurus Analysis:
2021 Jeep Grand Cherokee
With 61 currently listed for sale near Winnipeg, MB and an average price of $32,181.00 CAD, 36.1% of 2021 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2021 Jeep Grand Cherokee 4.62 / 5 stars.
100.0% of 2021 Grand Cherokee models on CarGurus are accident free.
The 2021 Jeep Grand Cherokee offers a spacious interior, smooth ride, and impressive power, all while retaining its rugged off-road capabilities.
CarGurus Analysis: 2021 Jeep Grand Cherokee
overall
Summary
With 61 currently listed for sale near Winnipeg, MB and an average price of $32,181.00 CAD, 36.1% of 2021 Jeep Grand Cherokees for sale on CarGurus are rated as good or great deals.
Favourably reviewed: Owners rated the 2021 Jeep Grand Cherokee 4.62 / 5 stars.
100.0% of 2021 Grand Cherokee models on CarGurus are accident free.
The 2021 Jeep Grand Cherokee offers a spacious interior, smooth ride, and impressive power, all while retaining its rugged off-road capabilities.
Why it stands out
The 2021 Jeep Grand Cherokee is a distinguished choice in the midsize SUV segment, appreciated for its blend of utility, luxury, and performance. It features a timeless design, reflecting both a rugged and upscale character, allowing it to appeal to a diverse range of buyers. The SUV is equipped with a powerful 3.6-litre Pentastar V6 engine as standard, with an optional 5.7-litre Hemi V8 for those seeking enhanced performance and towing capacity, making it suitable for various driving preferences, including off-road adventures. Inside, the Grand Cherokee offers a well-appointed cabin combining premium materials and sophisticated technology, although some users noted its tech features could benefit from updates. Furthermore, its strong accident-free record and favourable owner reviews highlight its reliability, making it an appealing option for those in the market for a dependable midsize SUV. However, prospective buyers should consider its relatively low safety ratings from the IIHS, which may be a concern for some.
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.
Relevant articles
Best SUVs in Canada for Towing 2026
If towing is paramount, then look no further. Here are the SUVs with the best towing capacities on sale in Canada today.
Best Camping Cars in Canada in 2026
Here’s a look at our ranking of the best vehicles to go camping with in 2026. We’ve chosen vehicles from a few different classes—from trucks to SUVs and even a minivan or two—to help you find the best fit for your lifestyle and budget.
Best SUVs for Snow in Canada in 2026
For those who live where snow performance is top of mind, we’ve compiled this list of the best SUVs for snow you can buy in Canada in 2026. These machines are ready to tackle just about any weather that’s thrown at you.
4.7 Overall rating
Filter by rating
Lee B
Reviewed a 2021 Jeep Grand Cherokee on May 7, 2026
Beautiful, solid, great stereo, comfortable seats, a high quality ride. Drives beautifully between 0 - 100 mph
Lee B
Reviewed a 2021 Jeep Grand Cherokee on May 7, 2026
Beautiful, solid, great stereo, comfortable seats, a high quality ride. Drives beautifully between 0 - 100 mph. No shakes or rattles. Very quiet cabin.
James H
Reviewed a 2021 Jeep Grand Cherokee on Apr 21, 2025
I'm a little biased because I've always driven Grand Cherokees. But I've always done that for a reason. Good quality, good features, great 4x4 capabilities and great handling.
Anonymous
Reviewed a 2021 Jeep Grand Cherokee on Aug 31, 2024
This vehicle is exactly what I expected from the Jeep brand . It has some great features, including panoramic sunroof. It would have been nice to have a CD player or a hard drive that holds CD recordings.
2021 Jeep Grand Cherokee Trims
| Trim type | MSRP |
|---|---|
| High Altitude 4WD | $54,175 |
| Overland 4WD | $51,230 |
| Limited X 4WD | $48,675 |
| 80th Anniversary Edition 4WD | $45,970 |
| Summit 4WD | $57,305 |
| Limited 4WD | $43,580 |
| Laredo 4WD | -- |
| Altitude 4WD | -- |
2021 Jeep Grand Cherokee Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Jeep Grand Cherokee prices has changed over time.
See more price trends
