Used 2019 Jeep Grand Cherokee for Sale nearWindsor, ON

How much does the 2019 Jeep Grand Cherokee cost?

Prices have softened 13.15% compared to this time last year, making it a favourable time to shop this model year.

There are 411 listings available, which suggests you should have a reasonable amount of choice.

Is the 2019 Jeep Grand Cherokee a good car?

Generally — the 4.39/5 user rating points to strong owner satisfaction. Owners commonly praise its smooth ride, spacious interior, and extensive features, and they also like its value and performance compared with competitors. For you, that makes sense if you want a used SUV that feels more premium than many mainstream rivals while still keeping Jeep’s off-road identity. With 33.3% of listings marked as good or great deals, there is also some room to shop selectively.

Is the 2019 Jeep Grand Cherokee reliable?

Owners rate it 4.39/5, a solid signal of long-term satisfaction.

The owner feedback also points to a dependable, trouble-free ownership experience for many drivers, with praise centred on comfort and everyday usability. That said, used buyers should still budget carefully for maintenance and inspect service history closely, since long-term ownership risk can rise if upkeep has been inconsistent.

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 afford to compare listings carefully before committing.

• Deal availability: 33.3% of listings are priced as good or great deals.
• Inventory: There are 411 listings available.
• Price trend: Prices have softened 13.15% compared with last year.

If you find a listing below $23,103 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 $23,686 CAD sits slightly below last year's $27,273 CAD.

That softer pricing can help you buy more confidently now, but it also means future resale upside may be more limited if the market stays soft. If you plan to sell later, the current trend suggests you should focus on condition, mileage, and service records to protect value. Well-kept examples should still appeal to shoppers who want a capable SUV with a premium feel.

Vehicles with solid owner satisfaction ratings, like this model year's 4.39/5, 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:

• 33.3% of listings are priced as good or great deals.
• Price trend: Prices have softened 13.15% compared with last year.
• Owners rate it 4.39/5 — a solid satisfaction signal.

Consider the 2020 if:

• At $26,467 CAD, the 2020 costs more than the current year's $23,686 CAD average.
• It adds a tenth-year update with familiar styling and a broader focus on comfort and performance.

The bottom line: Choose the 2019 if you want the better value and are comfortable shopping carefully for condition and history. If you can stretch your budget and want the newer year’s slightly updated package, the 2020 is the secondary path; price-sensitive buyers should stay focused on the 2019’s lower average cost and stronger deal availability.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.