Used 2019 Chrysler 300 for Sale nearMilwaukee, WI

How much does the 2019 Chrysler 300 cost?

Prices have softened 9.68% compared to this time last year, making it a favorable time to shop this model year.

There are 661 listings available, which gives you a solid pool of options to compare.

Is the 2019 Chrysler 300 a good car?

Yes — the 2019 Chrysler 300 earns a 4.6/5 user rating, which points to strong owner satisfaction. Owners consistently praise its smooth ride, spacious interior, and powerful engines, and many also like the value it offers for the price. In practical terms, that makes it a good fit if you want a roomy full-size sedan with a relaxed personality rather than something sporty or overly complicated. With 27.8% of listings marked as good or great deals, you still have room to shop selectively.

Is the 2019 Chrysler 300 reliable?

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

The owner feedback also emphasizes dependable everyday comfort, with repeated praise for the smooth ride and durable powertrains. That kind of pattern suggests the 300 can be a reassuring used buy if you prioritize a sedan you can count on for steady, low-drama ownership. For used buyers, the main long-term risk is less about the core mechanical character and more about finding a well-kept example with the right maintenance history.

What should I look for when buying a used 2019 Chrysler 300?

At 57% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should run a vehicle history report on every candidate and pay close attention to any prior collision records, title issues, or repeated repairs. A pre-purchase inspection should focus on body condition, alignment, and signs of uneven wear, since those can reveal whether a past incident was properly repaired. It also makes sense to prioritize cabin condition and feature operation, because this model’s appeal depends heavily on comfort and everyday usability.

Is now a good time to buy a used 2019 Chrysler 300?

This looks like a moderate, selective buyer’s market, so you can shop patiently but should move quickly on the best examples.

• Deal availability: 27.8% of listings are priced as good or great deals.
• Inventory: There are 661 listings available.
• Price trend: Prices have softened 9.68% compared with last year.
• Clean inventory: 57.0% of listings are accident-free.

If you find a listing below $15,476, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2019 Chrysler 300's resale value?

The current average of $15,542 sits slightly below last year's $17,209.

That softer pricing suggests the 2019 model has already moved into a more buyer-friendly part of its value curve, which can limit upside for a future seller. On the other hand, the 300’s roomy cabin, comfort-first character, and strong owner satisfaction can help keep demand steady among shoppers who want a large sedan with a traditional feel. If you buy well now and keep the car in good condition, you may be able to preserve more of its value than the broader market trend alone would suggest.

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 2019 Chrysler 300 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:

• 27.8% of listings are priced as good or great deals.
• At 57% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.68% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.

The bottom line: The 2019 is a smart choice if you want the Chrysler 300 with its later-run comfort, infotainment updates, and a market that still offers decent deal potential. If your priority is simply the lowest possible price, a nearby year may be worth comparing, but the 2019 is the better all-around pick if you want a balanced mix of value, comfort, and owner approval.

How does the 2019 Chrysler 300 compare to the 2019 Dodge Charger?

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

These recommendations are based on CarGurus' proprietary market data from October 21, 2026, CarGurus experts' opinions, and generative AI.