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428 listings
  • New Listing
    $35,998
    fair price
    $965 below market
    • 5,309 miles
    • 16 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from WA to VA*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Renton, WA / 2,432 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 Unavailable.

    Features and Specs:

    19 Combined MPG (16 City/25 Highway)

    Listing Information:

    VIN: 2C3CCABT6MH516001
    Stock: 27195182
    Certified Pre-Owned: No

  • Price Drop
    $26,487
    fair price
    $230 below market
    • 46,788 miles
    • No accidents, 1 owner, personal use only
    • 19 City / 30 Hwy MPG
    • Auto-Mattox (150 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Appomattox, VA / 150 miles away from Chesapeake, VA

    CARFAX One-Owner. Clean CARFAX. BACKUP CAMERA, BLUETOOTH, SUNROOF/MOONROOF, NAVIGATION, LEATHER SEATS, PUSH BUTTON START, APPLE CARPLAY / ANDROID AUTO...

    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: 2C3CCABG8PH565496
    Stock: M5120
    Certified Pre-Owned: No
    Listed since: 02-22-2025

  • $22,488
    fair price
    $1,076 below market
    • 42,298 miles
    • 1 accident, 2 owners, corporate fleet vehicle
    • 19 City / 30 Hwy MPG
    • Cox Chrysler Dodge Jeep Ram (184 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Burlington, NC / 184 miles away from Chesapeake, VA

    Summary- EXTENDED WARRANTY / MAINTENANCE PROTECTION AVAILABLE ... - LIFETIME ENGINE WARRANTY ... - Remainder of MANUFACTURER'S WARRANTY .....

    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: 2C3CCAEG7KH722617
    Stock: P22617
    Certified Pre-Owned: No
    Listed since: 05-01-2025

  • Price Drop
    $15,991
    fair price
    $641 above market
    • 109,026 miles
    • No accidents, 1 owner, rental vehicle
    • 18 City / 27 Hwy MPG
    • The Car Store (121 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Salisbury, MD / 121 miles away from Chesapeake, VA

    Bright White Clearcoat 2019 Chrysler 300 Limited AWD 8-Speed Automatic 3.6L 6-Cylinder SMPI DOHC18/27 City/Highway MPG

    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: Yes

    Features and Specs:

    21 Combined MPG (18 City/27 Highway)

    Listing Information:

    VIN: 2C3CCAKG2KH690891
    Stock: 33405
    Certified Pre-Owned: No
    Listed since: 04-04-2025

  • New Listing
    • 58,515 miles
    • 19 City / 30 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Atlanta, GA / 506 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 Unavailable.

    Features and Specs:

    23 Combined MPG (19 City/30 Highway)

    Listing Information:

    VIN: 2C3CCABG5MH660772
    Stock: 2003546193
    Certified Pre-Owned: No
    Listed since: 04-23-2025

  • Price Drop
    $19,500
    fair price
    $410 below market
    • 84,997 miles
    • 4 accidents, 2 owners, corporate fleet vehicle
    • 19 City / 30 Hwy MPG
    • CARMIX (135 mi away)
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Waldorf, MD / 135 miles away from Chesapeake, VA

    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: 2C3CCABG1MH523599
    Stock: 11042
    Certified Pre-Owned: No

  • Price Drop
    $15,390
    fair price
    $457 above market
    • 115,574 miles
    • No accidents, 2 owners, personal use only
    • 18 City / 27 Hwy MPG
    • Glen Burnie Auto Exchange (170 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Glen Burnie, MD / 170 miles away from Chesapeake, VA

    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:

    21 Combined MPG (18 City/27 Highway)

    Listing Information:

    VIN: 2C3CCAGG6KH517514
    Stock: U6617
    Certified Pre-Owned: No
    Listed since: 02-20-2025

  • New Listing
    • 73,111 miles
    • No accidents, 1 owner, personal use only
    • 19 City / 30 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Sacramento, CA / 2,452 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: 2C3CCAAG8MH572137
    Stock: 2003809432
    Certified Pre-Owned: No
    Listed since: 06-23-2025

  • New Listing
    $22,490
    fair price
    $476 below market
    • 54,729 miles
    • 19 City / 30 Hwy MPG
    • Easterns Automotive Group of Laurel (166 mi away)
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Laurel, MD / 166 miles away from Chesapeake, VA

    more

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    23 Combined MPG (19 City/30 Highway)

    Listing Information:

    VIN: 2C3CCABG9MH520353
    Stock: U520353
    Certified Pre-Owned: No
    Listed since: 05-20-2025

  • $21,995
    fair price
    $246 above market
    • 77,315 miles
    • No accidents, 3 owners, corporate fleet vehicle
    • 19 City / 30 Hwy MPG
    • Daxs Deals (190 mi away)
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Fayetteville, NC / 190 miles away from Chesapeake, VA

    Thank you for viewing our 2021 CHRYSLER 300 S V6 RWD for sale in Fayetteville, NC. If you have any specific questions please contact us. We will be gl...

    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: 2C3CCABG8MH529254
    Stock: 529254
    Certified Pre-Owned: No
    Listed since: 06-01-2025

  • New Listing
    $22,998
    fair price
    $542 below market
    • 59,831 miles
    • No accidents, 1 owner, rental vehicle
    • 19 City / 30 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to VA*
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Inglewood, CA / 2,364 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: 2C3CCABG9MH520160
    Stock: 27319515
    Certified Pre-Owned: No

  • $25,480
    fair price
    $164 above market
    • 59,210 miles
    • No accidents, 1 owner, personal use only
    • 19 City / 30 Hwy MPG
    • Auto-Mattox (150 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Appomattox, VA / 150 miles away from Chesapeake, VA

    CARFAX One-Owner. Clean CARFAX. BACKUP CAMERA, BLUETOOTH, SUNROOF/MOONROOF, NAVIGATION, LEATHER SEATS, PUSH BUTTON START, APPLE CARPLAY / ANDROID AUTO...

    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: 2C3CCABG1PH565517
    Stock: M5126
    Certified Pre-Owned: No
    Listed since: 02-27-2025

  • $23,849
    fair price
    $308 below market
    • 52,848 miles
    • No accidents, 2 owners, rental vehicle
    • 19 City / 30 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Wayne, NJ / 309 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: 2C3CCABGXMH545455
    Stock: 8D6RN3
    Certified Pre-Owned: No
    Listed since: 05-20-2025

  • $26,337
    fair price
    $175 above market
    • 51,587 miles
    • No accidents, 1 owner, rental vehicle
    • 19 City / 30 Hwy MPG
    • 1st Choice Motors (166 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Madison Heights, VA / 166 miles away from Chesapeake, VA

    CARFAX One-Owner. Clean CARFAX. This vehicle is located at 1st Choice Motors. 4799 S Amherst Hwy, Madison Heights, VA 24572.. Granite Crystal Metallic...

    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: 2C3CCABG0PH569512
    Stock: J5356
    Certified Pre-Owned: No
    Listed since: 03-10-2025

    • 48,779 miles
    • Frame damage reported, 3 owners, corporate fleet vehicle
    • 19 City / 30 Hwy MPG
    • Unlimited Auto Sales (147 mi away)
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Upper Marlboro, MD / 147 miles away from Chesapeake, VA

    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:

    23 Combined MPG (19 City/30 Highway)

    Listing Information:

    VIN: 2C3CCABG6MH550118
    Stock: 550118
    Certified Pre-Owned: No
    Listed since: 10-19-2024

  • New Listing
    $24,285
    fair price
    $89 above market
    • 39,750 miles
    • No accidents, 1 owner, personal use only
    • 19 City / 30 Hwy MPG
    • Richmond BMW of Midlothian (93 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Midlothian, VA / 93 miles away from Chesapeake, VA

    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
    $14,000
    fair price
    $90 above market
    • 105,724 miles
    • 1 accident, 1 owner, personal use only
    • 19 City / 30 Hwy MPG
    • Koons Ford Baltimore (180 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Baltimore, MD / 180 miles away from Chesapeake, VA

    Experience bold style and refined performance with the 2019 Chrysler 300 Touring. This full-size sedan blends luxury and comfort with a powerful 3.6L ...

    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: 2C3CCAAGXKH590894
    Stock: KH590894
    Certified Pre-Owned: No
    Listed since: 06-24-2025

    • 140 miles
    • No accidents, personal use only
    • 19 City / 30 Hwy MPG
    • Crossroads Ford of Wake Forest (141 mi away)
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Power Driver Seat
    • Tire Pressure Warnin...
    Close

    Located in Wake Forest, NC / 141 miles away from Chesapeake, VA

    Clean CARFAX. 2023 Chrysler Bright White Clearcoat 300 Touring

    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: 2C3CCAAG2PH677129
    Stock: PC7568
    Certified Pre-Owned: No
    Listed since: 06-11-2025

  • $25,750
    fair price
    $407 above market
    • 43,086 miles
    • No accidents, 1 owner, personal use only
    • 19 City / 30 Hwy MPG
    • Criswell Ford of Woodstock (193 mi away)
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Woodstock, VA / 193 miles away from Chesapeake, VA

    2023 Chrysler 300 Touring 4D Sedan Silver Mist Clearcoat RWD 3.6L V6 24V VVT 8-Speed Automatic**BALANCE OF FACTORY WARRANTY**, **LOCAL TRADE**, **ONE...

    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: 2C3CCADGXPH609298
    Stock: F250271A
    Certified Pre-Owned: No
    Listed since: 06-12-2025

  • $26,998
    fair price
    $586 above market
    • 29,119 miles
    • 1 accident, 2 owners, corporate fleet vehicle
    • 19 City / 30 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from KY to VA*
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Louisville, KY / 522 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: 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: 2C3CCABG7MH550032
    Stock: 26583840
    Certified Pre-Owned: No

  • $22,222
    fair price
    $787 above market
    • 72,937 miles
    • 1 accident, 2 owners, rental vehicle
    • 19 City / 30 Hwy MPG
    • Greenville AutoWorld (102 mi away)
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Greenville, NC / 102 miles away from Chesapeake, VA

    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: 2C3CCABG5MH520432
    Stock: 520432
    Certified Pre-Owned: No
    Listed since: 02-19-2025

Showing 43 - 63 out of 428 listings

Consumer Reviews for the Chrysler 300

Read recent reviews for the Chrysler 300
Overall Consumer Rating
4.6 out of 5 stars39 Reviews
Write a vehicle reviewSee all 39 reviews
  • 5 star
    (79%)
  • 4 star
    (13%)
  • 3 star
    (3%)
  • 2 star
    (3%)
  • 1 star
    (3%)
5 out of 5 stars

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!
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Used 2021 Chrysler 300 in Chesapeake, VA Values

Estimated values
2021 Chrysler 300 S 4dr Sedan (5.7L 8cyl 8A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$22,807$25,229$27,673
Clean$22,319$24,645$26,983
Average$21,507$23,671$25,834
Rough$20,452$22,406$24,341

The average list price of a used 2021 Chrysler 300 in Chesapeake, Virginia is $23,342. The average mileage on a used Chrysler 300 2021 for sale in Chesapeake, Virginia is 58,603. Based on the average mileage of 58,603 for used 2021 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 2021 in Chesapeake, Virginia to be $21,507.

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