Used 2021 Chrysler 300 for Sale near Connecticut

How much does the 2021 Chrysler 300 cost?

Prices have softened 9.52% compared to this time last year, making it a favorable time to shop this model year.

There are 511 listings available, which gives you a solid pool of options to compare on price and condition.

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 repeatedly praise the luxurious look, smooth ride, impressive handling, acceleration, and comfort. The cabin is also described as comfortable, quiet, and easy to use, which fits the car’s traditional big-sedan character and its appeal as a reasonably priced rear-wheel-drive luxury sedan.

The main trade-offs are poor value for money and some complaints about fuel efficiency, along with the loss of certain features in newer models. Even so, if you want a large sedan with old-school presence and a straightforward cabin, this model year still makes a strong case for itself.

There are 30.1% good or great deals in the market, so you can still find attractive pricing if you shop carefully.

Is the 2021 Chrysler 300 reliable?

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

The owner feedback points to a car that people feel good about living with over time, especially because they consistently mention comfort, quietness, and a smooth driving experience. That kind of feedback matters when you’re looking for a used sedan you can count on day after day.

The expert assessment also describes the car as quiet and capable on the road, with a traditional luxury feel that suits long-term ownership. It also notes a five-year, 60,000-mile powertrain warranty, which adds some reassurance for buyers.

For used shoppers, the main long-term risk is that age and feature packaging can make condition and equipment history more important than mileage alone.

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

At 66.1% 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 close inspection of body panels, paint consistency, and any signs of prior repair. Because advanced safety equipment is not uniformly standard, you should also confirm exactly which features are present on the specific car you’re considering.

Key things to evaluate:

• Trim level: The base 300 Touring uses 17-inch silver alloys, cloth upholstery, and an eight-way power driver’s seat, while the 300 Touring L adds Nappa leather upholstery and 18-inch polished alloys. The 300S stands out with standard 20-inch Black Noise wheels, perforated inserts, accent stitching, and heated front seats, making it the most upscale-feeling choice.
• 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 of torque, and all engines use an eight-speed automatic transmission.
• Safety package: All Chrysler 300s 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: The 8.4-inch Uconnect 4C touchscreen is standard across the lineup, and Apple CarPlay and Android Auto are standard as well. 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 RWD returns 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 the car’s traditional big-sedan feel. It makes sense if you want the lowest-cost way into the model, but it is also the least richly equipped.
• 300 Touring L: This is the best-value trim for most shoppers because it adds Nappa leather upholstery, 18-inch polished alloys, and access to more comfort and safety equipment. If you want the 300’s upscale character without jumping to the V8-focused top trim, this is the one to target.
• 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. It suits you best if you want the strongest performance and the most aggressive appearance.

Blind-spot monitoring and rear cross-traffic alert are only available on the Touring L or 300S, so those trims are the smarter picks if safety equipment matters to you.

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

This is a moderate market for selective buyers, so you can shop with some leverage if you focus on condition and pricing.

• Deal availability: 30.1% of listings are priced as good or great deals.
• Inventory: There are 511 listings available.
• Price trend: Prices have softened 9.52% compared with last year.
• Clean inventory: 66.1% of listings are accident-free.

If you find a listing below $19,892, 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 $19,892 sits slightly below last year's $21,984.

That price movement suggests the model has already absorbed some depreciation, which can help future sellers if they buy at the right number. If you purchase near the current average or below it, you may have less downside than someone who bought when prices were higher.

The car’s niche appeal also matters: buyers who want a traditional rear-wheel-drive luxury sedan with available V8 power tend to be more deliberate, which can support demand for clean examples. Well-kept cars with the right trim and equipment should be easier to position later than neglected or poorly documented ones.

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.

A key caveat is that advanced safety equipment is not evenly distributed across 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 forward collision warning, automatic emergency braking, adaptive cruise control, automatic high beams, lane departure warning, and rain-sensing wipers.

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:

• 30.1% of listings are priced as good or great deals.
• At 66.1% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 9.52% compared with last year.
• Owners rate it 4.6/5 — a strong satisfaction signal.
• You want a rare, reasonably priced rear-wheel-drive luxury sedan with available all-wheel drive or a 5.7-liter Hemi V8.

The bottom line: The 2021 Chrysler 300 is the right pick if you want classic big-sedan character, strong owner satisfaction, and a market that has cooled enough to create buying opportunities. If you’re especially price-sensitive, focus on well-kept Touring or Touring L examples; if you want the fullest expression of the car’s personality, the 300S is the better path.

These recommendations are based on CarGurus' proprietary market data from October 6, 2026, CarGurus experts' opinions, and generative AI.