Used 2014 Chrysler 300 for Sale nearMilwaukee, WI

How much does the 2014 Chrysler 300 cost?

Prices have held steady compared to this time last year, signaling a stable and predictable market for this model year.

There are 421 listings available, which gives you a moderate amount of inventory to compare before you buy.

Is the 2014 Chrysler 300 a good car?

Yes — the 4.6/5 user rating points to strong owner satisfaction. Owners consistently praise its luxury feel, power, and comfort, and many also like the spacious interior and the Hemi-powered driving experience. For you, that makes it a strong fit if you want a full-size sedan with a premium presence and everyday usability. With 26.6% of listings marked as good or great deals, there is still room to find a compelling value if you shop carefully.

Is the 2014 Chrysler 300 reliable?

Owners rate it 4.6/5, a strong signal of long-term satisfaction.

Owner feedback points to a car that many drivers find dependable and worth counting on for comfortable daily use, especially when they value its long-term appeal as a roomy sedan with strong power. The main ownership risk for used buyers is that earlier second-generation 300s have a weaker reliability record than later ones, so condition and maintenance history matter a lot.

What should I look for when buying a used 2014 Chrysler 300?

At 52.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report so you can separate clean examples from cars with prior damage. After that, prioritize a thorough pre-purchase inspection, with extra attention to suspension condition, electrical operation, and infotainment functionality. Because this model is valued for comfort and power, you should focus on overall condition and how well the car has been maintained rather than just the odometer reading.

Is now a good time to buy a used 2014 Chrysler 300?

This is a moderate, selective buyer’s market, so you can shop patiently but should move quickly when a strong listing appears.

• Deal availability: 26.6% of listings are priced as good or great deals.
• Inventory: There are 421 listings available.
• Price trend: Prices have held steady compared with last year.
• Clean inventory: 52.5% of listings are accident-free.

If you find a listing below $10,006, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2014 Chrysler 300's resale value?

The current average of $10,579 sits slightly above last year's $10,567.

That small increase suggests the market has been stable, which is helpful if you plan to resell later. A steady price trend usually means you are less likely to see sharp depreciation in the near term, especially if you buy a well-kept example at a fair price. Strong owner satisfaction also helps keep demand healthy when it is time to sell.

Vehicles with strong owner satisfaction ratings, like this model year's 4.6/5, tend to retain buyer demand, which supports resale value over time.

Should I buy a 2014 Chrysler 300 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:

• 26.6% of listings are priced as good or great deals.
• At 52.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have held steady compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.

The bottom line: You should lean toward the 2014 if you want the classic 300 formula: big-sedan space, strong power, and a stable used-car price. If you are especially price-sensitive, a nearby year may be worth comparing, but the 2014 remains a sensible choice when you find a clean, well-priced example with solid history and maintenance records.

These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.