Used 2020 Jeep Grand Cherokee for Sale nearMilton, ON

How much does the 2020 Jeep Grand Cherokee cost?

Prices have softened 16.30% compared to this time last year, making it a favourable time to shop this model year.

There are 575 listings available, which suggests you should have a reasonable amount of inventory to compare.

Is the 2020 Jeep Grand Cherokee a good car?

Yes — the 2020 Jeep Grand Cherokee earns a 4.58/5 user rating and a 6.33/10 expert rating.

The model scores 8/10 across Look and feel and Technology.

Owners consistently praise its comfort, performance, and luxurious features, and many highlight the powerful engines, especially the V8, along with the ride quality. The review summary also points to advanced safety options and a strong overall sense of satisfaction. On the other hand, the expert assessment notes that it is best suited to buyers who value character and capability more than the latest equipment, and it is described as poor value for money.

Given its overview as a two-row SUV with strong off-road ability and a familiar formula, it makes the most sense if you want traditional SUV character rather than the newest design or the best value. 32.2% of listings are priced as good or great deals, which gives you some room to shop selectively.

Is the 2020 Jeep Grand Cherokee reliable?

Owners rate it 4.58/5, a strong signal of long-term satisfaction.

The owner summary points to a vehicle that many drivers feel good about living with over time, especially because of its comfort, performance, and luxurious features. It also suggests the Grand Cherokee can be a dependable choice for buyers who value its character and capability, while still appreciating the strong satisfaction from current owners.

The expert driving notes also support that impression by describing the powertrain as satisfying and the SUV as capable in demanding conditions. If you buy used, the main long-term ownership risk is that some examples may have been used hard or may show wear in areas tied to its age and complexity.

What should I look for when buying a used 2020 Jeep Grand Cherokee?

Key things to evaluate:

• Trim level: Base versions miss some of the nicer touches found higher up the range, and the Premium Lighting Group is important because the headlights are rated poorly without the upgrade. If you want the best value, look for a trim that balances equipment with price rather than stretching too far into the expensive end, where hard plastics become more noticeable.
• Powertrain: The standard setup is a 295-horsepower, 3.6-litre V6 with an eight-speed automatic, while V8 options add more power and torque if you want stronger performance. The Trailhawk is the most off-road-focused version, and the Trackhawk and SRT are the performance-oriented choices.
• Safety package: ProTech I is standard and includes a reversing camera, parking sensors, blind-spot monitoring, and rear cross-traffic alert. ProTech II adds low-speed forward-collision warning, automatic emergency braking, lane-departure warning, lane-keeping assist, and automatic high-beam headlights, while Advanced ProTech II adds full-speed forward collision warning, adaptive cruise control with stop-and-go, semi-autonomous parking assist, and rain-sensing wipers.
• Infotainment: In Limited X trim, Uconnect includes an 8.4-inch touchscreen, navigation, Bluetooth, Apple CarPlay, Android Auto, and SiriusXM satellite radio connected services. A 4G LTE WiFi data plan is available, and some versions can be equipped with premium audio.
• Fuel efficiency: The standard V6 returned 11.3 litres per 100 kilometres in combined driving according to Natural Resources Canada, while the test vehicle recorded 12.1 L/100 km.

Which 2020 Jeep Grand Cherokee trim should I buy?

The 2020 Jeep Grand Cherokee is offered in 4 trim levels: Laredo, Limited X, SRT, Trackhawk.

Here's the short version:

• Laredo: This is the entry point, and it gives you the Grand Cherokee’s core styling and capability without pushing you into the pricier equipment levels. It makes sense if you want the nameplate and the basic SUV character, but not the higher-end extras.
• Limited X: This is the best-value choice if you want a more complete daily-driver package, because it adds the stronger infotainment setup, a more upscale feel, and the kind of equipment that makes the Grand Cherokee easier to live with every day.
• SRT: Choose this if you want serious performance, since it is one of the high-powered variants and is aimed at buyers who care more about speed and road presence than value.
• Trackhawk: This is the extreme performance pick, with the most outrageous power and the most specialised hardware in the lineup. It suits you only if you want maximum performance and are comfortable with the costs that come with it.

ProTech I is standard on all trim levels, while ProTech II and Advanced ProTech II add progressively more advanced driver-assistance features.

Is now a good time to buy a used 2020 Jeep Grand Cherokee?

This is a moderate market for selective buyers, so it pays to compare listings carefully and move quickly on the right one.

• Deal availability: 32.2% of listings are priced as good or great deals.
• Inventory: There are 575 listings available.
• Price trend: Prices have softened 16.30% compared with last year.

If you find a listing below $25,718 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2020 Jeep Grand Cherokee's resale value?

The current average of $25,718 CAD sits slightly below last year's $30,724 CAD.

That price movement suggests the market has already adjusted downward, which can make the vehicle more attractive to used buyers today. For a future seller, that also means resale value may be more sensitive to condition, mileage, and trim choice than it would be for a newer or more in-demand crossover.

Because the Grand Cherokee has a broad appeal and a strong enthusiast following, well-kept examples should still draw interest. Higher-spec versions with desirable equipment may hold up better than plain examples, especially if they are clean and properly maintained.

Vehicles with strong owner satisfaction ratings, like this model year's 4.58/5, tend to retain buyer demand, which supports resale value over time.

Is the 2020 Jeep Grand Cherokee safe?

The 2020 Jeep Grand Cherokee earns a four-star overall rating from NHTSA.

It earns a 3/10 safety score from our experts.

Jeep offers three different collections of advanced driving assistance systems for this model year. ProTech I is standard on all trim levels and includes a reversing camera, parking sensors, blind-spot monitoring, and rear cross-traffic alert. ProTech II adds low-speed forward-collision warning, automatic emergency braking, lane-departure warning, lane-keeping assist, and automatic high-beam headlights. Advanced ProTech II adds full-speed forward collision warning, adaptive cruise control with stop-and-go, semi-autonomous parking assist, and rain-sensing wipers.

The main caution is that the crash-test results are weak for a vehicle in this class, and advanced safety features are not standard across the lineup. Headlights also rate poorly unless you upgrade to the better lighting package.

Should I buy a 2020 Jeep Grand Cherokee or consider a different year?

If you're weighing the 2020 against nearby model years, here's how to think about it:

Choose the 2020 if:

• 32.2% of listings are priced as good or great deals.
• Price trend: Prices have softened 16.30% compared with last year.
• Owners rate it 4.58/5 — a strong satisfaction signal.
• It keeps the familiar Grand Cherokee formula, with strong off-road capability and a wide range of trims.

Consider the 2021 if:

• At $29,478 CAD, the 2021 costs more than the current year's $25,718 CAD average.
• It is the final version before the redesigned Grand Cherokee arrives.

The bottom line: If you want the better price and are comfortable with the older-generation formula, the 2020 is the smarter buy. If you prefer to wait for the last year of this generation and are willing to pay more, the 2021 is the alternative to consider.

These recommendations are based on CarGurus' proprietary market data from October 13, 2026, CarGurus experts' opinions, and generative AI.