Used 2016 Jeep Grand Cherokee for Sale nearWindsor, ON

How much does the 2016 Jeep Grand Cherokee cost?

Prices have softened 24.58% compared to this time last year, making it a favourable time to shop this model year.

There are 183 listings available, which gives you a reasonable amount of choice in the used market.

Is the 2016 Jeep Grand Cherokee a good car?

Yes — the 4.8/5 user rating points to strong owner satisfaction. Owners consistently praise its comfort, performance, and luxurious features, and many also like the spacious interior and the powerful Hemi engine. If you want an SUV that feels more polished than rugged on the road but still has real trail ability, this model year fits that brief well. With 19.7% of listings marked as good or great deals, you still have some room to shop selectively.

Is the 2016 Jeep Grand Cherokee reliable?

Owners rate it 4.8/5, a strong signal of long-term satisfaction.

The owner feedback points to a vehicle that many people find dependable in day-to-day use, with comfort and performance standing out over the long haul. That said, the broader model history suggests you should pay close attention to maintenance records and overall condition, because used ownership risk can rise quickly if prior care was inconsistent.

Is now a good time to buy a used 2016 Jeep Grand Cherokee?

This looks like a moderate, selective buyer’s market, so you can afford to be choosy without waiting forever for the right example.

• Deal availability: 19.7% of listings are priced as good or great deals.
• Inventory: There are 183 listings available.
• Price trend: Prices have softened 24.58% compared with last year.

If you find a listing below $15,602 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2016 Jeep Grand Cherokee's resale value?

The current average of $15,602 CAD sits slightly below last year's $20,687 CAD.

That price movement suggests the market has already adjusted downward, which can help you buy at a more favourable entry point today. For a future seller, it also means resale value may be more sensitive to condition, mileage, and service history than to age alone. Well-kept examples should hold up better than neglected ones, especially when buyers are comparing them against newer alternatives.

Vehicles with strong owner satisfaction ratings, like this model year's 4.8/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2016 Jeep Grand Cherokee or consider a different year?

If you're weighing the 2016 against nearby model years, here's how to think about it:

Choose the 2016 if:

• 19.7% of listings are priced as good or great deals.
• Price trend: Prices have softened 24.58% compared with last year.
• Owners rate it 4.8/5 — a strong satisfaction signal.

The bottom line: The 2016 is a strong pick if you want the Grand Cherokee’s comfort, capability, and upscale feel at a more attractive price than many newer examples. If you’re price-sensitive, it makes sense to focus on the best-maintained 2016 listings first, since the lower average price and decent deal availability give you a solid shopping window. If you want to stretch your budget further, compare nearby years only after you’ve checked condition and service history carefully.

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