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414 listings
- New Listing$19,998good price$1,315 below market
- 50,454 miles
- No accidents, 2 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
Close
Located in Las Vegas, NV / 2,149 miles away from Chesapeake, VA
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: 2C3CCAAG4LH239111
Stock: 27114639
Certified Pre-Owned: No - 63,426 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Oklahoma City, OK / 1,187 miles away from Chesapeake, VA
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: 2C3CCAAG6LH209222
Stock: 2003898386
Certified Pre-Owned: No
Listed since: 07-25-2025- $14,499good price$1,843 below market
- 108,780 miles
- 3 accidents, 3 owners, rental vehicle
- 19 City / 30 Hwy MPG
- John Hiester Chrysler Dodge Jeep Ram of Sanford (185 mi away)
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Located in Sanford, NC / 185 miles away from Chesapeake, VA
LOCAL TRADE, FAST AND EASY FINANCING, THE NEW PRICE OUTLET, 1-YR SiriusXM Guardian Trial, 10 Beats Premium Speakers w/Subwoofer, 300S Premium Group, 5...
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: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCABG1JH243810
Stock: N25430H
Certified Pre-Owned: No
Listed since: 08-06-2025 - $24,700good price$1,809 below market
- 24,358 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Buchanan Kia (196 mi away)
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Located in Westminster, MD / 196 miles away from Chesapeake, VA
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: 2C3CCAAG6NH139594
Stock: KX7283
Certified Pre-Owned: No
Listed since: 12-20-2024 - Price Drop$28,998fair price$511 above market
- 20,032 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from LA to VA*
Close
Located in Baton Rouge, LA / 958 miles away from Chesapeake, VA
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: 2C3CCABG1NH228858
Stock: 27325670
Certified Pre-Owned: No - $15,995good price$1,519 below market
- 100,236 miles
- 1 accident, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Eagle Auto Outlet (122 mi away)
Close
Located in Fredricksburg, VA / 122 miles away from Chesapeake, VA
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: 2C3CCAAG2LH128413
Stock: EGL1213
Certified Pre-Owned: No
Listed since: 08-26-2025 - New Listing$22,398fair price$639 below market
- 58,910 miles
- No accidents, 1 owner, rental vehicle
- 19 City / 30 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Highlands Ranch, CO / 1,561 miles away from Chesapeake, VA
Transfer of vehicle from another location to your neighborhood Enterprise Car Sales may require payment of a non-refundable transfer fee to begin the ...
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: 2C3CCAAG1NH187116
Stock: 8D8RLL
Certified Pre-Owned: No
Listed since: 08-20-2025 - $27,998fair price$65 above market
- 25,145 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
Close
Located in Wichita, KS / 1,152 miles away from Chesapeake, VA
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: 2C3CCABG1NH236412
Stock: 27325696
Certified Pre-Owned: No - New Listing$27,998fair price
- 26,985 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TX to VA*
Close
Located in Houston, TX / 1,200 miles away from Chesapeake, VA
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: 2C3CCABGXNH236408
Stock: 27565797
Certified Pre-Owned: No - $20,590fair price$361 above market
- 24,903 miles
- No accidents, 3 owners, personal use
- 19 City / 30 Hwy MPG
- Carvana - Richmond (95 mi away)
- Home delivery*
Close
Located in Richmond, VA / 95 miles away from Chesapeake, VA
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: 2C3CCAAG2JH144334
Stock: 2003835819
Certified Pre-Owned: No
Listed since: 06-28-2025 - $26,388fair price$341 below market
- 46,250 miles
- No accidents, 1 owner, personal use
- 19 City / 30 Hwy MPG
- Matthews Motors Clayton (148 mi away)
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Located in Clayton, NC / 148 miles away from Chesapeake, VA
**Save time, Buy Online with Matthews Motors Express Point.Click.Buy**We have over 300 certified pre-owned vehicles, most come with a lifetime powertr...
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: 2C3CCABG3NH245225
Stock: 30056
Certified Pre-Owned: No
Listed since: 03-09-2025 - $24,998fair price$181 below market
- 47,846 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from GA to VA*
Close
Located in Buford, GA / 473 miles away from Chesapeake, VA
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: 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: 2C3CCADGXNH121076
Stock: 27606043
Certified Pre-Owned: No - $18,577good price$963 below market
- 91,470 miles
- 2 accidents, 3 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Matthews Motors Goldsboro (136 mi away)
Close
Located in Goldsboro, NC / 136 miles away from Chesapeake, VA
**Save time, Buy Online with Matthews Motors Express Point.Click.Buy**We have over 300 certified pre-owned vehicles, most come with a lifetime powertr...
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: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAEG5LH108523
Stock: G8529
Certified Pre-Owned: No
Listed since: 05-24-2024 - $27,998fair price$199 below market
- 46,479 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from LA to VA*
Close
Located in Shreveport, LA / 1,036 miles away from Chesapeake, VA
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: Yes
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: 2C3CCADG8NH143514
Stock: 27254031
Certified Pre-Owned: No - Price Drop$18,990fair price$895 above market
- 55,541 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana - Richmond (95 mi away)
- Home delivery*
Close
Located in Richmond, VA / 95 miles away from Chesapeake, VA
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: 2C3CCAAG7JH275968
Stock: 2003993958
Certified Pre-Owned: No
Listed since: 08-29-2025 - New Listing$15,950fair price$290 below market
- 79,281 miles
- 1 accident, 3 owners, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- Westgate Chrysler Jeep Dodge Ram (152 mi away)
Close
Located in Raleigh, NC / 152 miles away from Chesapeake, VA
Apple CarPlay/Android Auto, Quick Order Package 22E Touring, 4-Wheel Disc Brakes, 6 Speakers, ABS brakes, Air Conditioning, Alloy wheels, AM/FM radio:...
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: No
Features and Specs:
23 Combined MPG (19 City/30 Highway)
Listing Information:
VIN: 2C3CCAAG2JH341004
Stock: JH341004
Certified Pre-Owned: No
Listed since: 09-02-2025 - $28,998fair price$486 above market
- 19,802 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
Close
Located in Merriam, KS / 1,014 miles away from Chesapeake, VA
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: 2C3CCABG8NH256401
Stock: 27325709
Certified Pre-Owned: No - Price Drop$29,998
- 19,500 miles
- No accidents, 1 owner, corporate fleet vehicle
- 19 City / 30 Hwy MPG
- CarMax (In-stock online)
- Transfer available from KS to VA*
Close
Located in Wichita, KS / 1,152 miles away from Chesapeake, VA
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: 2C3CCABGXNH241253
Stock: 27325673
Certified Pre-Owned: No - 105,151 miles
- No accidents, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana - Richmond (95 mi away)
- Home delivery*
Close
Located in Richmond, VA / 95 miles away from Chesapeake, VA
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: 2C3CCAAG9JH275695
Stock: 2003916682
Certified Pre-Owned: No
Listed since: 07-26-2025- $23,538fair price$349 above market
- 79,260 miles
- No accidents, 2 owners, personal use only
- 19 City / 30 Hwy MPG
- Casey Chevrolet (22 mi away)
Close
Located in Newport News, VA / 22 miles away from Chesapeake, VA
Just Arrived!, Actual MPG rating will vary with options, driving conditions, habits and vehicle condition., 300S Premium Group, 300S Premium Group 2, ...
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: 2C3CCABT6LH180767
Stock: CX90702
Certified Pre-Owned: No
Listed since: 03-13-2025 - $24,590fair price$1,027 below market
- 29,637 miles
- 1 accident, 1 owner, personal use only
- 19 City / 30 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Birmingham, AL / 637 miles away from Chesapeake, VA
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: 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: 2C3CCAAG7NH111805
Stock: 2003977143
Certified Pre-Owned: No
Listed since: 08-14-2025
Showing 85 - 105 out of 414 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 2020 Chrysler 300 in Chesapeake, VA Values
Estimated values
2020 Chrysler 300 Touring 4dr Sedan (3.6L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $15,920 | $18,703 | $21,398 |
| Clean | $15,506 | $18,194 | $20,790 |
| Average | $14,816 | $17,346 | $19,775 |
| Rough | $13,920 | $16,243 | $18,457 |
The average list price of a used 2020 Chrysler 300 in Chesapeake, Virginia is $22,913. The average mileage on a used Chrysler 300 2020 for sale in Chesapeake, Virginia is 53,497. Based on the average mileage of 53,497 for used 2020 Chrysler 300 for sale in Chesapeake, VA 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 2020 in Chesapeake, Virginia to be $14,816.
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