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66 listings
  • Price Drop
    $23,984
    great price
    $3,918 below market
    • 39,301 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Ann Arbor, MI / 556 miles away from Chesapeake, VA

    Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Navigation System,Satellite Radio,WiFi Hotspot,V6 Cylinder Engine,Power Door Lo...

    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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG8NC141620
    Stock: NC141620P
    Certified Pre-Owned: Yes

  • Price Drop
    $19,369
    great price
    $2,986 below market
    • 62,133 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 19 City / 26 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Oxnard, CA / 2,402 miles away from Chesapeake, VA

    CarFax 1-Owner,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Navigation System,Satellite Radio,WiFi Hotspot,V6 Cyli...

    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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEAG8NC171422
    Stock: NC171422P
    Certified Pre-Owned: No

  • New Listing
    $27,998
    great price
    $2,567 below market
    • 46,855 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from CA to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Bakersfield, CA / 2,374 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG3NC118276
    Stock: 27288387
    Certified Pre-Owned: No

  • $25,455
    great price
    $2,295 below market
    • 56,520 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Yorkville, NY / 444 miles away from Chesapeake, VA

    CarFax 1-Owner,High Value Options,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Navigation...

    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/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG6NC116974
    Stock: D116974A
    Certified Pre-Owned: No

  • Price Drop
    $26,650
    great price
    $2,879 below market
    • 38,830 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Wexford, PA / 339 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,...

    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/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG1NC117594
    Stock: H117594A
    Certified Pre-Owned: No

  • Price Drop
    $30,990
    great price
    $2,489 below market
    • 22,022 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Cleveland, OH / 440 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: 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG6NC114352
    Stock: 2003714340
    Certified Pre-Owned: No
    Listed since: 05-14-2025

  • New Listing
    • 11,377 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Coon Rapids, MN / 1,062 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Ke...

    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/25 Highway)

    Listing Information:

    VIN: 1C4RJFAGXNC141618
    Stock: RC712127A
    Certified Pre-Owned: Yes

  • $21,699
    great price
    $2,593 below market
    • 66,764 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 19 City / 26 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Wesley Chapel, FL / 686 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,...

    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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG2NC171169
    Stock: NC171169
    Certified Pre-Owned: No

  • Price Drop
    $26,173
    good price
    $2,047 below market
    • 24,858 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Albany, NY / 433 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,...

    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/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG4NC163078
    Stock: NC163078A
    Certified Pre-Owned: Yes

  • Price Drop
    $27,498
    good price
    $2,003 below market
    • 33,862 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Hamilton, NJ / 256 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,...

    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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG5NC119170
    Stock: NC119170U
    Certified Pre-Owned: No

  • New Listing
    $29,998
    good price
    $1,317 below market
    • 23,543 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from Fredericksburg, VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Fredericksburg, VA / 126 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG2NC115630
    Stock: 27485779
    Certified Pre-Owned: No

  • Price Drop
    $28,590
    good price
    $1,972 below market
    • 34,633 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in Cleveland, OH / 440 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: 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG8NC112912
    Stock: 2003641269
    Certified Pre-Owned: No
    Listed since: 04-10-2025

  • Price Drop
    $23,998
    good price
    $1,086 below market
    • 53,475 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Medford, OR / 2,480 miles away from Chesapeake, VA

    CarFax 1-Owner,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Navigation System,R...

    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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG4NC162786
    Stock: 162786A
    Certified Pre-Owned: No

  • Price Drop
    $29,260
    fair price
    $338 below market
    • 30,081 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Billings, MT / 1,779 miles away from Chesapeake, VA

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyl...

    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/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG9NC148110
    Stock: 53234BM
    Certified Pre-Owned: No

  • Price Drop
    $24,787
    fair price
    $950 below market
    • 44,210 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 18 City / 25 Hwy MPG
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Klamath Falls, OR / 2,425 miles away from Chesapeake, VA

    Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Navigation System,Remote Start,Sat...

    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/25 Highway)

    Listing Information:

    VIN: 1C4RJFAGXNC162629
    Stock: NC162629
    Certified Pre-Owned: No

  • $24,898
    fair price
    $880 below market
    • 54,323 miles
    • No accidents, 1 owner, rental vehicle
    • 5 Seats, 19 City / 26 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Jacksonville, FL / 537 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG1NC126174
    Stock: 7VMPWX
    Certified Pre-Owned: No
    Listed since: 04-14-2025

  • New Listing
    $29,998
    good price
    $1,724 below market
    • 31,029 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from MN to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Maplewood, MN / 1,046 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFBG8NC144810
    Stock: 26717784
    Certified Pre-Owned: No

  • New Listing
    $26,998
    fair price
    $442 above market
    • 28,266 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 18 City / 25 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from MD to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Sunroof/Moonroof
    Close

    Located in White Marsh, MD / 182 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:

    21 Combined MPG (18 City/25 Highway)

    Listing Information:

    VIN: 1C4RJFAG8NC141102
    Stock: 26924845
    Certified Pre-Owned: No

  • $25,398
    fair price
    $135 below market
    • 57,817 miles
    • No accidents, 1 owner, personal use only
    • 5 Seats, 19 City / 26 Hwy MPG
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    • Blind Spot Monitorin...
    Close

    Located in Marietta, GA / 505 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: 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 (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEAG8NC155804
    Stock: 7V3WKF
    Certified Pre-Owned: No
    Listed since: 04-23-2025

    • 27,295 miles
    • No accidents, 1 owner, personal use
    • 5 Seats, 19 City / 26 Hwy MPG
    • CarMax (In-stock online)
    • Transfer available from TX to VA*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Austin, TX / 1,306 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG9NC127962
    Stock: 27201805
    Certified Pre-Owned: No

  • $22,990
    fair price
    $369 below market
    • 74,709 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5 Seats, 19 City / 26 Hwy MPG
    • Carvana (In-stock online)
    • Home delivery*
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    • Sunroof/Moonroof
    Close

    Located in Phoenix, AZ / 2,024 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: 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:

    21 Combined MPG (19 City/26 Highway)

    Listing Information:

    VIN: 1C4RJEBG0NC125677
    Stock: 2003656287
    Certified Pre-Owned: No
    Listed since: 04-17-2025

Showing 1 - 21 out of 66 listings

Buying a Jeep Grand Cherokee WK in Chesapeake Virginia

For those living in Chesapeake, VA, the Jeep Grand Cherokee WK stands out as a practical choice for exploring the region's natural beauty. Its impressive off-roading capability makes it well-suited for adventures in the nearby Great Dismal Swamp, where rugged terrain can challenge even the most determined adventurer. With a robust towing capacity, this SUV can handle recreational trailers or boats for weekend getaways to local lakes and rivers.

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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.