Used 2020 Chrysler 300 for Sale nearRaleigh, NC
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gloss Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Smoke/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 111,215
- Stock #:
- P253384
- VIN:
- 2C3CCABG1LH253384

Sponsored Listing
2020 Chrysler 300
S RWD
111,215 mi
$15,696
- Year:
- 2021
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,610
- Stock #:
- 516148
- VIN:
- 2C3CCAAG8MH516148

Sponsored Listing
2021 Chrysler 300
Touring RWD
78,610 mi
$19,798
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 147,032
- Stock #:
- 9307A
- VIN:
- 2C3CCABGXKH686734

-$279
2019 Chrysler 300
S RWD
147,032 mi
$12,594
$12,315
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gloss Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Smoke/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 111,215
- Stock #:
- P253384
- VIN:
- 2C3CCABG1LH253384

2020 Chrysler 300
S RWD
111,215 mi
$15,696
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Red
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,984
- Stock #:
- 590617
- VIN:
- 2C3CCAAG6KH590617

-$500
2019 Chrysler 300
Touring RWD
78,984 mi
$15,767
$15,266
- Year:
- 2021
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 119,586
- Stock #:
- P1984
- VIN:
- 2C3CCABG0MH660629

2021 Chrysler 300
S V6 RWD
119,586 mi
$16,536
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Velvet Red Pearlcoat
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,647
- Stock #:
- FL8221
- VIN:
- 2C3CCAAGXKH548158

2019 Chrysler 300
Touring RWD
96,647 mi
$16,202
- Year:
- 2021
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,610
- Stock #:
- 516148
- VIN:
- 2C3CCAAG8MH516148

2021 Chrysler 300
Touring RWD
78,610 mi
$19,798
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 151,295
- Stock #:
- 158643
- VIN:
- 2C3CCABG6LH158643

2020 Chrysler 300
S RWD
151,295 mi
$13,394
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 46,647
- Stock #:
- 28617606
- VIN:
- 2C3CCAAG6LH233472

2020 Chrysler 300
Touring RWD
46,647 mi
$23,497
- Year:
- 2021
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Blue (Frostbite)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 86,081
- Stock #:
- 529605
- VIN:
- 2C3CCARG3MH529605

2021 Chrysler 300
Touring L AWD
86,081 mi
$19,137
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Purple
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,035
- Stock #:
- 28033783
- VIN:
- 2C3CCAAG2LH164389

2020 Chrysler 300
Touring RWD
50,035 mi
$22,547
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Gray (Ceramic Grey Clearcoat)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 79,428
- Stock #:
- 65242
- VIN:
- 2C3CCABG2KH516724

2019 Chrysler 300
S RWD
79,428 mi
$18,094
CarGurus Analysis:
2020 Chrysler 300
With 66 currently listed for sale near Raleigh, NC and an average price of $12,599, 12.1% of 2020 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Chrysler 300 4.78 / 5 stars.
60.6% of 2020 Chrysler 300 models on CarGurus are accident free.
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- White
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,214
- VIN:
- 2C3CCAAG9KH682935

2019 Chrysler 300
Touring L RWD
48,214 mi
$18,746
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Amethyst
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 69,079
- Stock #:
- I225625
- VIN:
- 2C3CCAAG9LH225625

2020 Chrysler 300
Touring RWD
69,079 mi
$19,864
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Canyon Sunset
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 46,126
- Stock #:
- GAM6635
- VIN:
- 2C3CCAAG9LH239203

2020 Chrysler 300
Touring RWD
46,126 mi
$20,332
- Year:
- 2021
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 71,112
- Stock #:
- A2F-20535
- VIN:
- 2C3CCAAG9MH620535

-$400
2021 Chrysler 300
Touring RWD
71,112 mi
$20,887
$20,487
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 71,727
- Stock #:
- 8823
- VIN:
- 2C3CCAEG2LH124467

2020 Chrysler 300
Limited RWD
71,727 mi
$19,370
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 77,226
- Stock #:
- LH128058
- VIN:
- 2C3CCAAG8LH128058

2020 Chrysler 300
Touring RWD
77,226 mi
$17,650
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Gloss Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,380
- Stock #:
- S131551
- VIN:
- 2C3CCAAG7LH131551

2020 Chrysler 300
Touring RWD
103,380 mi
$15,367
- Year:
- 2019
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 141,746
- Stock #:
- U260809161T1
- VIN:
- 2C3CCAAG0KH610537

-$190
2019 Chrysler 300
Touring RWD
141,746 mi
$11,452
$11,262
- Year:
- 2020
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 292 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 109,621
- Stock #:
- 115519
- VIN:
- 2C3CCAEG5LH115519

2020 Chrysler 300
Limited RWD
109,621 mi
$13,888
- Year:
- 2021
- Make:
- Chrysler
- Model:
- 300
- Body type:
- Sedan
- Doors:
- 4 doors
- Drivetrain:
- Rear-Wheel Drive
- Engine:
- 300 hp 3.6L V6
- Exterior color:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 109,226
- Stock #:
- 692AKR
- VIN:
- 2C3CCABG2MH545693

2021 Chrysler 300
S V6 RWD
109,226 mi
$17,561
CarGurus Analysis: 2020 Chrysler 300

Summary
With 66 currently listed for sale near Raleigh, NC and an average price of $12,599, 12.1% of 2020 Chrysler 300s for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2020 Chrysler 300 4.78 / 5 stars.
60.6% of 2020 Chrysler 300 models on CarGurus are accident free.
Why it stands out
The 2020 Chrysler 300 stands out as a big rear-wheel-drive sedan that still delivers classic American luxury-car presence. By this point in its run, the 300 had already been updated with a softer, less self-consciously retro look, and its cabin had received major upgrades. It also benefited from the more upscale interior design introduced in the 2015 refresh, which helped keep the car feeling current even as its basic formula stayed familiar.
What makes the 2020 model especially appealing is the combination of space, durability, and available equipment. Chrysler’s 3.6-liter Pentastar V6 and 5.7-liter Hemi V8 gave buyers a choice of tough, durable engines, and all versions used automatic transmissions. The 300 also offered all-wheel drive on V6 models, while the UConnect system had already gained Apple CarPlay and Android Auto. Buyers looking for a large sedan with a roomy cabin and a smooth, quiet character could still find a lot to like here.
There are tradeoffs, though. The 300’s size comes with a big appetite for fuel, and it is not as performance focused as its Dodge Charger sibling. Reliability is generally better in later examples, but the earliest years of the LD generation had the worst record, and complaints were higher in the 2011 and 2012 models than in later years. Even so, the 2020 Chrysler 300 remains distinctive for offering full-size comfort, rear-drive character, and a traditional sedan feel in a market that had largely moved away from cars like it.
Other model years to consider
- Average price: $10,848
- Good/great deal percentage: 31.4%
- User rating: 5 / 5
- Total listings: 51
- Average price: $15,760
- Good/great deal percentage: 25.0%
- User rating: 4.9 / 5
- Total listings: 64
- Average price: $11,299
- Good/great deal percentage: 21.0%
- User rating: 4.75 / 5
- Total listings: 62
This analysis is based on CarGurus' proprietary market data from September 21, 2026, CarGurus experts' opinions, and generative AI.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
4.8 Overall rating
Filter by rating
Philip D
Reviewed a 2020 Chrysler 300 on Mar 12, 2024
Nice features. The car is missing a warranty and a new tire.
Glen S
Reviewed a 2020 Chrysler 300 on Jul 31, 2023
It was a lovely car. Quiet and smooth riding. There were a few maintenance issues but nothing that couldnt be fixed.
MICHAEL M
Reviewed a 2020 Chrysler 300 on Nov 19, 2020
Best sedan in its category. Built well and updated but not drastically changed over time. Lot of room inside and solid construction. Very quiet ride and good power. Gets 20 MPG in city and about 28 MPG on highway. I love mine and used low mileage vehicle are a bargain.
Christopher T
Reviewed a 2020 Chrysler 300 on Jun 9, 2021
It’s a Quality Automobile which is Durable, Spacious, Reliable, with Great Value. My next Car will be a 2019 or 2020 Chrysler 300 Limited.
2020 Chrysler 300 Trims
| Trim type | MSRP |
|---|---|
| Touring L AWD | $36,065 |
| Touring AWD | $32,790 |
| Touring L RWD | $33,315 |
| S AWD | $39,445 |
| Limited AWD | $41,345 |
| Limited RWD | $38,595 |
| S RWD | $36,995 |
| Touring RWD | $30,040 |
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
2020 Chrysler 300 Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2020 Chrysler 300 prices has changed over time.
See more price trends2020 Chrysler 300 Pricing Analysis: Raleigh, NC Market Report
Pricing by Nearby Locations
Market Area: Raleigh, NC
Key Insights
- Highest Prices in Greenville: The market in Greenville, NC ($24,795) shows the highest average price, likely due to a combination of demand and limited inventory.
- Lowest Prices in Goldsboro and Rocky Mount: Both Goldsboro, NC and Rocky Mount, NC offer the lowest average prices at $18,697, indicating a more price-sensitive market or higher inventory turnover.
- Inventory Variation: Markets like Greensboro (74 listings) and Winston Salem (76 listings) have moderate inventory levels, with average prices around $17,733 to $18,416, suggesting stable pricing dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Greenville, NC | 63 | $24,795 |
| Goldsboro, NC | 64 | $18,697 |
| Rocky Mount, NC | 66 | $18,697 |
| Greensboro, NC | 74 | $17,733 |
| Danville, VA | 72 | $17,733 |
| Martinsville, VA | 75 | $17,433 |
| Winston Salem, NC | 76 | $18,416 |
| New Bern, NC | 62 | $24,795 |
Pricing Analysis by Model Year
Key Insights
- New Model Retains Value: The 2023 Chrysler 300 is priced at $34,197, which is only −0.3% below its original MSRP, indicating strong demand for the latest model.
- Significant Depreciation for Older Models: The 2019 Chrysler 300 shows a steep decline, priced at $13,358, reflecting a −54.3% depreciation from its original MSRP.
- Best Value in Recent Years: The 2021 Chrysler 300 is priced at $18,999, which is −40.0% below its original MSRP, making it a compelling option for budget-conscious buyers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2023 Chrysler 300 | $34,295 | $34,197 | -0.3% |
| 2022 Chrysler 300 | $33,545 | $15,360 | -54.2% |
| 2021 Chrysler 300 | $31,875 | $18,999 | -40.0% |
| 2019 Chrysler 300 | $29,220 | $13,358 | -54.3% |
| 2018 Chrysler 300 | $28,995 | $11,299 | -61.0% |
| 2017 Chrysler 300 | $32,340 | $10,848 | -66.4% |
| 2016 Chrysler 300 | $32,260 | $9,833 | -69.5% |
| 2015 Chrysler 300 | $31,695 | $11,406 | -64.0% |
| 2014 Chrysler 300 | $30,995 | $8,032 | -74.0% |
| 2013 Chrysler 300 | $30,345 | $9,976 | -67.2% |
These recommendations are based on CarGurus' proprietary market data from September 23, 2026, CarGurus experts' opinions, and generative AI.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
How much does the 2020 Chrysler 300 cost?
| Metric | Value |
|---|---|
| Current Average Price | $18,376 |
| Year-Round Low | $17,798 |
| Year-Round High | $20,229 |
| Average Price a Year Ago | $20,234 |
| Change vs. Last Year | −9.18% |
Prices have softened 9.18% compared to this time last year, making it a favorable time to shop this model year.
There are 620 listings available, which suggests you should have a reasonable amount of inventory to compare.
Is the 2020 Chrysler 300 a good car?
Yes — the 4.78/5 user rating points to strong owner satisfaction. Drivers commonly praise its smooth and quiet ride, good power, and ample space, and many also like its affordability and design. That fits especially well if you want a roomy, comfortable sedan with a traditional full-size feel and easy-to-use technology. With 30.3% of listings marked as good or great deals, the market still offers some attractive opportunities.
Is the 2020 Chrysler 300 reliable?
Owners rate it 4.78/5, a strong signal of long-term satisfaction.
User feedback describes the 2020 Chrysler 300 as well-built, smooth, quiet, and durable, with many owners appreciating its dependable character and strong everyday usability. The combination of good power and a comfortable ride also supports the impression that it can be a car you can count on over time.
For used buyers, that means long-term ownership risk looks manageable if you choose carefully and verify the car’s condition and history.
What should I look for when buying a used 2020 Chrysler 300?
At 57.4% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
You should start with a vehicle history report and confirm whether any prior damage was repaired properly. A pre-purchase inspection is especially important on a large sedan like this, where you want to check for signs of uneven wear, bodywork, or neglected maintenance. Focus on overall condition, because the best examples are likely to be the ones that have been cared for consistently.
Is now a good time to buy a used 2020 Chrysler 300?
This looks like a moderate, selective buyer’s market, so you can shop patiently but should move quickly on the best listings.
- Deal availability: 30.3% of listings are priced as good or great deals.
- Inventory: There are 620 listings available.
- Price trend: Prices have softened 9.18% compared with last year.
- Clean inventory: 57.4% of listings are accident-free.
If you find a listing below $17,798, that's toward the low end of the year-round range and worth acting on quickly.
What is the 2020 Chrysler 300's resale value?
The current average of $18,376 sits slightly below last year's $20,234.
That price movement suggests the 2020 Chrysler 300 has already absorbed some depreciation, which can help future resale stability if you buy at the right price. A lower entry cost today can make it easier to limit your loss when you eventually sell. The strongest examples will usually be the ones with clean history, solid maintenance, and broad appeal to shoppers who want a large, comfortable sedan.
Vehicles with strong owner satisfaction ratings, like this model year's 4.78/5, tend to retain buyer demand, which supports resale value over time.
Should I buy a 2020 Chrysler 300 or consider a different year?
If you're weighing the 2020 against nearby model years, here's how to think about it:
Choose the 2020 if:
- 30.3% of listings are priced as good or great deals.
- At 57.4% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
- Price trend: Prices have softened 9.18% compared with last year.
- Owners rate it 4.78/5 — a strong satisfaction signal.
Consider the 2021 if:
- At $20,206, the 2021 costs more than the current year's $18,376 average.
- It adds a more upscale-feeling cabin and remains appealing as a rear-wheel-drive luxury sedan.
The bottom line: If you want the better value, the 2020 is the stronger starting point because it costs less and still delivers the core Chrysler 300 experience. If you’re willing to pay more for a newer model year, the 2021 is the secondary path to consider, especially if you want the slightly fresher package and can justify the higher price.
These recommendations are based on CarGurus' proprietary market data from September 22, 2026, CarGurus experts' opinions, and generative AI.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
Relevant articles

Chrysler 300 Buying Guide: Cost, Reliability, and the Best Years to Buy
Discover the ultimate buying guide for purchasing a used Chrysler 300, covering every generation since the modern 300 debuted in 2005. Whether you're a first-time buyer or a Chrysler enthusiast, this comprehensive overview will help you research your next pre-owned Chrysler 300.

Who Makes Chrysler Cars?
Chrysler is a long-running American legacy, founded in 1925. Though it was once a premier American luxury brand, things are quieter there now, as it only sells three variants of a minivan. It is a division of Stellantis, which is also the parent company of Jeep, Dodge, Ram, and others.