Used 2014 Jeep Grand Cherokee for Sale nearWinnipeg, MB

How much does the 2014 Jeep Grand Cherokee cost?

Prices are up 1.86% year-over-year — a sign of continued demand for this model year.

There are 141 listings available, which gives you a reasonable amount of choice when comparing condition, mileage, and trim.

Is the 2014 Jeep Grand Cherokee a good car?

Yes — the 4.7/5 user rating points to strong owner satisfaction. Drivers consistently praise its spacious interior, luxurious features, and impressive power, especially in the diesel model. The comfortable ride and high-tech options also stand out, and the Grand Cherokee’s mix of daily usability, towing ability, and rough-road capability makes it appealing if you want one SUV to cover several jobs. With 27.0% of listings marked as good or great deals, there are still some attractive opportunities in the market.

Is the 2014 Jeep Grand Cherokee reliable?

Owners rate it 4.7/5, a strong signal of long-term satisfaction.

The user feedback also points to a vehicle that many owners find dependable in day-to-day use, with praise for its comfort and capability over the long term. At the same time, some owners mention reliability concerns and expensive repairs tied to certain features, so you should pay close attention to service history and how the vehicle was maintained.

For used buyers, the main long-term ownership risk is that repair costs can rise quickly if the previous owner skipped maintenance or if the vehicle has feature-heavy equipment that needs attention.

Is now a good time to buy a used 2014 Jeep Grand Cherokee?

This looks like a moderate market for selective buyers, so it makes sense to shop carefully and compare listings.

• Deal availability: 27.0% of listings are priced as good or great deals.
• Inventory: There are 141 listings available.
• Price trend: Prices are up 1.86% year-over-year.

If you find a listing below $13,570 CAD, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2014 Jeep Grand Cherokee's resale value?

The current average of $14,408 CAD sits slightly above last year's $14,145 CAD.

That modest increase suggests the market has held up reasonably well for this model year, which is a positive sign if you plan to sell later. The current pricing also sits within a fairly tight year-round range, which can help support predictable resale expectations. If demand stays steady, well-kept examples should remain easier to move than neglected ones.

Vehicles with strong owner satisfaction ratings, like this model year's 4.7/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2014 Jeep Grand Cherokee or consider a different year?

If you're weighing the 2014 against nearby model years, here's how to think about it:

Choose the 2014 if:

• 27.0% of listings are priced as good or great deals.
• Price trend: Prices are up 1.86% year-over-year.
• Owners rate it 4.7/5 — a strong satisfaction signal.

The bottom line: The 2014 is a strong choice if you want a Grand Cherokee that blends capability, comfort, and a more premium feel, especially if you value the updated styling and added driver-assist features. If your priority is stretching your budget further, a nearby year with a lower average price may be worth a look, but the 2014 remains the better all-around pick if you want a well-rounded balance of features and buyer appeal.

How does the 2014 Jeep Grand Cherokee compare to the 2014 Ford Explorer?

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