Used 2019 Jeep Grand Cherokee for Sale nearWindsor, ON

How much does the 2019 Jeep Grand Cherokee cost?

Prices have softened 14.23% compared to this time last year, making it a favourable time to shop this model year.

There are 389 listings available, which suggests a healthy amount of inventory for used shoppers.

Is the 2019 Jeep Grand Cherokee a good car?

Generally — the 2019 Jeep Grand Cherokee earns 4.4/5 from owners, which points to strong overall satisfaction. Owners commonly praise its smooth ride, spacious interior, and extensive features, and they also value its performance and the way it compares with competitors. In practical terms, that makes it a compelling choice if you want a used SUV that feels more premium than many mainstream rivals while still offering real off-road capability and everyday comfort. The market also shows 32.4% of listings as good or great deals, which gives you some room to shop selectively.

Is the 2019 Jeep Grand Cherokee reliable?

Owners rate it 4.4/5, a solid signal of long-term satisfaction.

Owners describe it as dependable in day-to-day use, with a reputation that supports trouble-free ownership for many buyers. The strongest owner feedback centres on its smooth ride, spacious cabin, and the sense that it delivers lasting value over time. Even so, used buyers should keep an eye on long-term ownership risk because this model year’s broader reliability record is mixed.

Is now a good time to buy a used 2019 Jeep Grand Cherokee?

This looks like a moderate, selective buyer’s market, so you can shop patiently and still find worthwhile options.

• Deal availability: 32.4% of listings are priced as good or great deals.
• Inventory: There are 389 listings available.
• Price trend: Prices have softened 14.23% compared with last year.

If you find a listing below $23,085 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2019 Jeep Grand Cherokee's resale value?

The current average of $23,085 CAD sits slightly below last year's $26,916 CAD.

That price movement suggests the market has already adjusted downward, which can make the model easier to buy now but may also limit upside for a future seller. If you plan to resell later, the current softness means your return will depend more on condition, mileage, and equipment than on broad market momentum. Vehicles with solid owner satisfaction ratings, like this model year's 4.4/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2019 Jeep Grand Cherokee or consider a different year?

If you're weighing the 2019 against nearby model years, here's how to think about it:

Choose the 2019 if:

• 32.4% of listings are priced as good or great deals.
• Price trend: Prices have softened 14.23% compared with last year.
• Owners rate it 4.4/5 — a solid satisfaction signal.

Consider the 2020 if:

• At $25,176 CAD, the 2020 costs more than the current year's $23,085 CAD average.
• It adds a fresher update cycle with a more polished feel.

The bottom line: The 2019 is the better pick if you want stronger value and a lower entry price, especially given the current market softness. If you can stretch for the 2020 and want the newer-year alternative, that makes sense too, but price-sensitive buyers should focus on the 2019 first.

How does the 2019 Jeep Grand Cherokee compare to the 2019 Ford Explorer?

Read our full side-by-side expert comparison here.

These recommendations are based on CarGurus' proprietary market data from November 10, 2026, CarGurus experts' opinions, and generative AI.