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468 listings
- New Listing$21,900good price$1,132 below market
- 76,529 miles
- No accidents, 3 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Sebar (23 mi away)
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Located in Greensboro, NC / 23 miles away from Winston Salem, NC
The 2021 Chrysler 300 S is a full-size sedan that combines classic American design with modern performance and technology.Under the hood, it features ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG5MH538025
Stock: S538025
Certified Pre-Owned: No
Listed since: 04-25-2025 - New Listing$19,995fair price$223 below market
- 97,677 miles
- No accidents, 2 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Sebar (23 mi away)
Close
Located in Greensboro, NC / 23 miles away from Winston Salem, NC
A stylish full-size sedan!?The 2021 Chrysler 300 S is a full-size sedan that combines bold styling with robust performance and modern features.Equippe...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG6MH554380
Stock: S554380
Certified Pre-Owned: No
Listed since: 03-21-2025 - Price Drop$21,999fair price$1,145 above market
- 65,255 miles
- No accidents, 2 owners, personal use only
- 19 City / 30 Hwy MPG
- Stokes Hodges Ford (198 mi away)
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Located in Graniteville, SC / 198 miles away from Winston Salem, NC
This vehicle comes equipped with Quick Order Package 2EE, Sport Appearance Package (Black Chrome Surround 300S Grille, Black Headlamp Bezels, Black LE...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAG8MH538148
Stock: F4069A
Certified Pre-Owned: No
Listed since: 07-27-2025 - Price Drop
- 71,932 miles
- 1 accident, 4 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Capital Blvd DriveTime (95 mi away)
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Located in Raleigh, NC / 95 miles away from Winston Salem, NC
Shop at DriveTime: Get started on your personalized car-buying journey today. With no credit impact, you can get approved for your real, personalized ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: Yes
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAGXMH511985
Stock: 1190216826
Certified Pre-Owned: No
Listed since: 06-25-2025 - Price Drop$23,200great price$6,044 below market
- 50,833 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Jerry Hunt Supercenter (18 mi away)
- Home delivery*
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Located in Lexington, NC / 18 miles away from Winston Salem, NC
Priced below KBB Fair Purchase Price! CARFAX One-Owner. Carfax Accident Free, One Owner, Leather Interior, Panoramic Sunroof, Push to Start, Navigatio...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG9LH128326
Stock: 23273
Certified Pre-Owned: No
Listed since: 07-19-2025 - New Listing$21,590
- 95,086 miles
- No accidents, 3 owners, rental vehicle
- 19 City / 30 Hwy MPG
- Carvana - Richmond (181 mi away)
- Home delivery*
Close
Located in Richmond, VA / 181 miles away from Winston Salem, NC
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG4MH554703
Stock: 2003931461
Certified Pre-Owned: No
Listed since: 08-01-2025 - $30,990
- 61,341 miles
- No accidents, 1 owner, personal use only
- 16 City / 25 Hwy MPG
- Carvana - Richmond (181 mi away)
- Home delivery*
Close
Located in Richmond, VA / 181 miles away from Winston Salem, NC
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
19 Combined MPG (16 City/25 Highway)
Listing Information:
VIN: 2C3CCABT0MH512137
Stock: 2003883041
Certified Pre-Owned: No
Listed since: 07-22-2025 - $24,990good price$1,817 below market
- 20,431 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana - Richmond (181 mi away)
- Home delivery*
Close
Located in Richmond, VA / 181 miles away from Winston Salem, NC
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAG2LH120232
Stock: 2003855658
Certified Pre-Owned: No
Listed since: 06-28-2025 - $19,980good price$2,763 below market
- 77,253 miles
- No accidents, 3 owners, rental vehicle
- 19 City / 30 Hwy MPG
- Herlong Ford (186 mi away)
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Located in Edgefield, SC / 186 miles away from Winston Salem, NC
Chrysler 300 S 3.6L V6 24V VVT 8-Speed Automatic4G LTE Wi-Fi Hot Spot, 6 Premium Alpine Speakers, ABS brakes, Apple CarPlay, Cruise Control, Dual Fro...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG9LH137267
Stock: T8040B
Certified Pre-Owned: No
Listed since: 03-29-2025 - $27,990good price$1,093 below market
- 25,142 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana - Charlotte (68 mi away)
- Home delivery*
Close
Located in Charlotte, NC / 68 miles away from Winston Salem, NC
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCADG2NH131035
Stock: 2003909461
Certified Pre-Owned: No
Listed since: 07-20-2025 - $22,990fair price$84 below market
- 78,936 miles
- No accidents, 2 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Carvana - Richmond (181 mi away)
- Home delivery*
Close
Located in Richmond, VA / 181 miles away from Winston Salem, NC
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG1NH187485
Stock: 2003855695
Certified Pre-Owned: No
Listed since: 07-10-2025 - New Listing$23,998fair price$319 above market
- 43,175 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax Raleigh (86 mi away)
Close
Located in Raleigh, NC / 86 miles away from Winston Salem, NC
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAG5NH131017
Stock: 27575019
Certified Pre-Owned: No - $20,399fair price$615 below market
- 85,493 miles
- 1 accident, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Rocky Mount Chrysler Dodge Jeep Ram FIAT (136 mi away)
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Located in Rocky Mount, NC / 136 miles away from Winston Salem, NC
CARFAX One-Owner. Bright White Clearcoat 2022 Chrysler 300 Touring RWD 8-Speed Automatic 3.6L V6 24V VVT 19/30 City/Highway MPG At Rocky Mount Chrysle...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAG0NH139588
Stock: J5009A
Certified Pre-Owned: No
Listed since: 07-21-2025 - 23,736 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana - Charlotte (68 mi away)
- Home delivery*
Close
Located in Charlotte, NC / 68 miles away from Winston Salem, NC
At Carvana, we go miles beyond the extra mile. That's why we provide you with a convenient, fast, and hassle-free car buying experience that puts you ...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAG4LH172056
Stock: 2003894437
Certified Pre-Owned: No
Listed since: 07-15-2025- Price Drop$21,900great price$3,588 below market
- 39,750 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Richmond BMW of Midlothian (175 mi away)
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Located in Midlothian, VA / 175 miles away from Winston Salem, NC
RECALL NOTICE: Some vehicles offered for sale may be subject to unrepaired manufacturer safety recalls. To determine the recall status of a vehicle, v...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAGXPH556218
Stock: CBML250235A
Certified Pre-Owned: No
Listed since: 06-26-2025 - New Listing$26,500
- 87,415 miles
- No accidents, 2 owners, personal use only
- Sebar (23 mi away)
Close
Located in Greensboro, NC / 23 miles away from Winston Salem, NC
The 2020 Chrysler 300 S with the 5.7-liter V8 engine is a bold and powerful full-size sedan that blends classic American muscle with modern luxury. Eq...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 2C3CCABT3LH217287
Stock: S217287
Certified Pre-Owned: No
Listed since: 07-04-2025 - New Listing$27,998
- 48,044 miles
- No accidents, 3 owners, corporate fleet vehicle
- CarMax Fayetteville (101 mi away)
Close
Located in Fayetteville, NC / 101 miles away from Winston Salem, NC
CarMax values transparency and wants you to love your next car, not settle on it. Certain vehicles may have unrepaired safety recalls. Check nhtsa.gov...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 2C3CCABT1LH189523
Stock: 27208415
Certified Pre-Owned: No - Price Drop$22,901
- 91,635 miles
- Frame damage reported, 3 owners, rental vehicle
- Sir Walter Chevrolet (86 mi away)
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Located in Raleigh, NC / 86 miles away from Winston Salem, NC
**2020 Chrysler 300 S V8**âś… 5.7L HEMI V8 Engineâś… 8-Speed Automatic Transmissionâś… Rear-Wheel Driveâś… Leather-Trimmed Sport Seatsâś… Heated and Venti...
AutoCheck Vehicle History Summary
Accident Free Vehicle: No
Personal Use Only: No
History Provider: AutoCheck
Title Details: Issue reported
Salvage Vehicle: No
Frame Damage: Yes
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 2C3CCABT9LH233834
Stock: 254885C
Certified Pre-Owned: No
Listed since: 07-05-2025 - New Listing$24,291
- 95,757 miles
- No accidents, 3 owners, corporate fleet vehicle
- Autova (112 mi away)
Close
Located in Madison Heights, VA / 112 miles away from Winston Salem, NC
This 2020 Silver Mist Clearcoat Chrysler 300 S RWD 5.7 is well equipped and includes these features and benefits:Autova is Central VA's Premier Use...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
Listing Information:
VIN: 2C3CCABTXLH180819
Stock: 16140
Certified Pre-Owned: No
Listed since: 08-02-2025 - $25,588great price$3,309 below market
- 28,510 miles
- No accidents, 1 owner, rental vehicle
- 19 City / 30 Hwy MPG
- Carolina Mitsubishi - High Point (15 mi away)
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Located in High Point, NC / 15 miles away from Winston Salem, NC
Thank you for viewing this quality pre-owned 2023 Chrysler 300 300S RWD offered in Silver Mist Clearcoat with the Black Leather interior!This 300 come...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: No
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG7PH633433
Stock: PM1131
Certified Pre-Owned: No
Listed since: 07-08-2025 - $22,495good price$1,715 below market
- 20,732 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Ilderton Dodge Chrysler Jeep Ram (17 mi away)
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Located in High Point, NC / 17 miles away from Winston Salem, NC
Summary*All ILDERTON CDJR Advertised Prices Include $1,000 FINANCE CASH **ILDERTON CDJR Finance Cash is only available on preowned vehicles f...
AutoCheck Vehicle History Summary
Accident Free Vehicle: Yes
Personal Use Only: Yes
History Provider: AutoCheck
Title Details: Clean Title
Salvage Vehicle: No
Frame Damage: No
Theft History: No
Lemon Status: No
Free History Report: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAEG6KH684183
Stock: 684183P
Certified Pre-Owned: No
Listed since: 07-01-2025
Showing 1 - 21 out of 468 listings
Consumer Reviews for the Chrysler 300
Read recent reviews for the Chrysler 300
Best car for the dollar!
Jacob, 03/27/2019
2019 Chrysler 300 C 4dr Sedan (5.7L 8cyl 8A)
Dollar for dollar there is no better!!! Came from an S -Class, while the 300 is down a rung or two from that , I only paid a third of the price. 33% of the price for 80% of the experience is a WIN-WIN for the 300C. 300 and Hemi never stop pleasing!
UPDATE - 3 years later and still great! Buy one while you still can!
Used 2021 Chrysler 300 in Winston Salem, NC Values
Estimated values
2021 Chrysler 300 S 4dr Sedan (3.6L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $19,648 | $21,548 | $23,466 |
| Clean | $19,229 | $21,049 | $22,882 |
| Average | $18,529 | $20,218 | $21,907 |
| Rough | $17,619 | $19,137 | $20,641 |
The average list price of a used 2021 Chrysler 300 in Winston Salem, North Carolina is $23,875. The average mileage on a used Chrysler 300 2021 for sale in Winston Salem, North Carolina is 61,174. Based on the average mileage of 61,174 for used 2021 Chrysler 300 for sale in Winston Salem, NC and using an average vehicle condition rating, which means the vehicle may have a few mechanical and/or cosmetic problems and may require a considerable amount of reconditioning, we appraise the average trade-in value of a used Chrysler 300 2021 in Winston Salem, North Carolina to be $18,529.
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