Used 2021 Chrysler 300 for Sale nearOrlando, FL

How much does the 2021 Chrysler 300 cost?

Prices have softened 9.95% compared to this time last year, making it a favorable time to shop this model year.

There are 520 listings available, which suggests you have a workable amount of inventory to compare.

If you find a listing below $20,303.11, that's toward the low end of the year-round range and worth acting on quickly.

Is the 2021 Chrysler 300 a good car?

Yes — the 2021 Chrysler 300 earns a 4.6/5 user rating and a 7.67/10 expert rating. The standout strength is Technology at 9/10.

Owners consistently praise the luxurious look, smooth ride, impressive handling, acceleration, and comfort. The cabin also gets credit for being quiet and easy to live with, which fits the car’s relaxed, upscale character.

The main trade-off is value: the expert review calls it poor value for money, and owners also mention fuel-efficiency concerns along with the loss of some features in newer models. That makes it a better fit if you want a traditional luxury sedan formula rather than the newest feature set.

The 2021 Chrysler 300 is aimed at buyers who want a reasonably priced luxury sedan with rear-wheel-drive character, available all-wheel drive, and even a V8 option. In market terms, 23.7% of listings are good or great deals, so there is some room to shop selectively.

Is the 2021 Chrysler 300 reliable?

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

The owner summary points to a vehicle that feels luxurious, smooth, comfortable, and impressive to drive, while also highlighting the kind of dependable everyday appeal that keeps buyers coming back. The expert review also describes it as quiet, capable, and comfortable on the road, which supports the idea that it is built for steady use rather than constant fuss.

For maintenance, the warranty coverage is described as mid-pack, with a three-year, 36,000-mile basic warranty and five-year, 60,000-mile powertrain protection.

For used buyers, the main long-term risk is less about outright character and more about how well the car was maintained, since older luxury sedans can become expensive if prior care was inconsistent.

What should I look for when buying a used 2021 Chrysler 300?

At 68.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle-history report and then prioritize a pre-purchase inspection, especially if the car has had bodywork or multiple owners. Focus on condition, maintenance records, and whether the equipment you want is actually present, since advanced safety features are tied to higher trims and packages.

Key things to evaluate:

• Trim level: The base 300 Touring uses cloth upholstery and 17-inch silver alloys, while the Touring L adds Nappa leather and 18-inch polished alloys. The 300S stands out with standard 20-inch Black Noise wheels, perforated inserts, accent stitching, and a more upscale appearance, so it is the trim to target if you want the strongest mix of style and equipment.
• Powertrain: The 3.6-liter Pentastar V6 makes 292 horsepower and 260 pound-feet of torque in the Touring and Touring L, while the 300S gets 300 horsepower and 264 pound-feet. The 300S also offers a 5.7-liter V8 with 363 horsepower and 394 pound-feet, and all versions use an eight-speed automatic; rear-wheel drive is standard and all-wheel drive is available on most trims.
• Safety package: All models include active head restraints, airbags, traction and stability control with brake assist, rain brake support, ready alert braking, and hill start assist. Blind-spot monitoring and rear cross-traffic alert are only available on the Touring L or 300S, and the SafetyTec Plus Group adds forward collision warning, automatic emergency braking, adaptive cruise control, automatic high beams, lane departure warning, and rain-sensing wipers.
• Infotainment: Every trim gets the 8.4-inch Uconnect 4C touchscreen, Apple CarPlay, and Android Auto. If you want more tech, the Popular Equipment Group adds a 506-watt amp, nine Alpine speakers, GPS navigation, SiriusXM Traffic Plus, surround sound, a trunk-mounted subwoofer, and a dual-pane sunroof.
• Fuel efficiency: The V6 with rear-wheel drive is rated at 19 mpg city, 30 mpg highway, and 23 mpg combined. AWD lowers that to 18 mpg city, 27 mpg highway, and 21 mpg combined, while the V8-powered 300S returns 16 mpg city, 25 mpg highway, and 19 mpg combined.

Which 2021 Chrysler 300 trim should I buy?

The 2021 Chrysler 300 is offered in 3 trim levels: 300 Touring, 300 Touring L, 300S.

Here's the short version:

• 300 Touring: This is the entry point, and it gives you the core Chrysler 300 experience with the V6, rear-wheel drive, the 8.4-inch touchscreen, Apple CarPlay, Android Auto, and a comfortable, quiet cabin. It makes sense if you want the least expensive way into the model, but it is also the trim with the fewest upscale touches.
• 300 Touring L: This is the best-value trim for most shoppers because it adds Nappa leather, 18-inch polished alloys, and access to more comfort and safety equipment. If you want the 300’s luxury feel without jumping to the highest-priced version, this is the one to focus on.
• 300S: This is the most distinctive trim, with standard 20-inch Black Noise wheels, perforated inserts, accent stitching, paddle shifters, and the option of the 5.7-liter V8. Choose it if you want the strongest style and performance character in the lineup.

Blind-spot monitoring and rear cross-traffic alert are only available on the Touring L or 300S, and the SafetyTec Plus Group adds several advanced driver-assistance features.

Is now a good time to buy a used 2021 Chrysler 300?

This looks like a moderate, selective buyer’s market, so you can shop with some leverage if you are patient.

• Deal availability: 23.7% of listings are priced as good or great deals.
• Inventory: There are 520 listings available.
• Price trend: Prices have softened 9.95% compared with last year.
• Clean inventory: 68.8% of listings are accident-free.

If you find a listing below $20,303.11, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2021 Chrysler 300's resale value?

The current average of $20,283 sits slightly below last year's $22,524.

That decline suggests the market has already adjusted downward, which can help you buy at a more favorable point in the cycle. For a future seller, that also means resale upside may be more limited unless the car is especially clean, well equipped, and documented.

The good news is that the 300 still has a clear identity: rear-wheel-drive luxury-sedan character, available V8 power, and a comfortable cabin. Those traits can help sustain interest among shoppers who want something traditional and distinctive.

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.

Is the 2021 Chrysler 300 safe?

The 300 received top "Good" scores in all Insurance Institute for Highway Safety (IIHS) crash tests except the small overlap tests, where it received a "Marginal" score. It also received a "Poor" rating for headlights. Over at the National Highway Traffic Safety Administration (NHTSA), the 300 received a four-star overall crash test rating, with four-star driver and passenger side crash test ratings, and a four-star rollover rating. On the plus side, it received a five-star rating for NHTSA's combined side barrier and side pole crash test.

It earns a 7/10 safety score from our experts.

All Chrysler 300s offer active head restraints, an arsenal of airbags, traction and stability control with brake assist, rain brake support, ready alert braking, and hill start assist.

Advanced safety equipment is not as evenly distributed as it is in some rivals, since blind-spot monitoring, rear cross-traffic alert, and the SafetyTec Plus Group features are tied to higher trims and packages. The headlight rating is also a notable weak point to keep in mind.

Should I buy a 2021 Chrysler 300 or consider a different year?

If you're weighing the 2021 against nearby model years, here's how to think about it:

Choose the 2021 if:

• 23.7% of listings are priced as good or great deals.
• At 68.8% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.95% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• It combines a traditional rear-wheel-drive luxury-sedan layout with available all-wheel drive and a V8 option.

The bottom line: The 2021 Chrysler 300 makes the most sense if you want a distinctive, comfortable sedan with old-school character and you are willing to shop carefully for condition and equipment. If your priority is the lowest possible purchase price, a nearby model year may be worth comparing, but the 2021 stands out as the better-balanced choice when you want a mix of value, comfort, and personality.

These recommendations are based on CarGurus' proprietary market data from August 28, 2026, CarGurus experts' opinions, and generative AI.