Skip to Filters
61 listings
- Price Drop$30,531fair price$801 above market
- 36,400 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 25 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Yorkville, NY / 444 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: 1C4RJFBG6NC129318
Stock: D129318A
Certified Pre-Owned: No - $27,998fair price$357 below market
- 44,393 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from OH to VA*
Close
Located in Columbus, OH / 429 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:
21 Combined MPG (18 City/25 Highway)
Listing Information:
VIN: 1C4RJFBG6NC139802
Stock: 27177445
Certified Pre-Owned: No - New Listing$22,999good price$2,102 below market
- 54,540 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 18 City / 25 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in East Amherst, NY / 455 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 (18 City/25 Highway)
Listing Information:
VIN: 1C4RJFAG9NC162802
Stock: 8DGQSJ
Certified Pre-Owned: No
Listed since: 05-24-2025 - Price Drop$27,398good price$905 below market
- 61,009 miles
- 1 accident, 1 owner, personal use only
- 5 Seats, 18 City / 25 Hwy MPG
- Driveway (In-stock online)
- Home delivery*
Close
Located in Johnston, IA / 995 miles away from Chesapeake, VA
CarFax 1-Owner,Back-Up Camera,Blind Spot Monitor,Brake Assist,Heated Seats,Heated Steering Wheel,Lane Keeping Assist,Navigation System,Premium Sound,R...
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:
21 Combined MPG (18 City/25 Highway)
Listing Information:
VIN: 1C4RJFAG7NC146355
Stock: NC146355V
Certified Pre-Owned: No - $29,990fair price$786 below market
- 34,729 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 25 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Indianapolis, IN / 579 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: 1C4RJFAG6NC147061
Stock: 2003760043
Certified Pre-Owned: No
Listed since: 05-22-2025 - $24,898fair price$740 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*
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 - $26,998fair price$431 below market
- 57,829 miles
- 1 accident, 2 owners, personal use only
- 5 Seats, 18 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
Close
Located in Memphis, TN / 766 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: 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: 1C4RJFBG4NC138101
Stock: 27103218
Certified Pre-Owned: No - $29,999fair price$40 above market
- 26,546 miles
- No accidents, 2 owners, personal use
- 5 Seats, 19 City / 26 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Peoria, AZ / 2,033 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: 1C4RJEAG2NC153630
Stock: 8GNC9R
Certified Pre-Owned: No
Listed since: 04-08-2025 - $23,398good price$1,374 below market
- 61,955 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 19 City / 26 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Sanford, FL / 622 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: 1C4RJEBG5NC126016
Stock: 7VMCRM
Certified Pre-Owned: No
Listed since: 01-13-2025 - $23,898good price$1,453 below market
- 56,790 miles
- No accidents, 1 owner, rental vehicle
- 5 Seats, 19 City / 26 Hwy MPG
- Enterprise Car Sales (In-stock online)
- Home delivery*
Close
Located in Miami, FL / 806 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: 1C4RJEBG3NC125947
Stock: 7VQFJQ
Certified Pre-Owned: No
Listed since: 03-06-2025 - $26,804fair price$533 below market
- 43,237 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 25 Hwy MPG
- RubyCar - Nashville (In-stock online)
- Home delivery*
Close
Located in Mount Juliet, TN / 573 miles away from Chesapeake, VA
Certified. Certification Program Details: Type your description here Priced below KBB Fair Purchase Price! Clean CARFAX. CARFAX One-Owner. RubyCar by ...
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: 1C4RJFBG4NC138583
Stock: 92331724
Certified Pre-Owned: No
Listed since: 02-01-2024 - $26,991fair price$911 below market
- 37,605 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 25 Hwy MPG
- RubyCar - Southern California (In-stock online)
- Home delivery*
Close
Located in San Diego, CA / 2,319 miles away from Chesapeake, VA
Certified. Certification Program Details: Type your description here Priced below KBB Fair Purchase Price! Clean CARFAX. CARFAX One-Owner. RubyCar by ...
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: 1C4RJFBG1NC110580
Stock: 98525416
Certified Pre-Owned: No
Listed since: 02-01-2024 - $24,990fair price
- 53,889 miles
- No accidents, 1 owner, personal use only
- 5 Seats, 18 City / 25 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,380 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:
21 Combined MPG (18 City/25 Highway)
Listing Information:
VIN: 1C4RJFAG7NC117180
Stock: 2003707018
Certified Pre-Owned: No
Listed since: 05-16-2025 - New Listing$27,998fair price$1,422 above market
- 26,586 miles
- 5 Seats, 19 City / 26 Hwy MPG
- CarMax (In-stock online)
- Transfer available from NV to VA*
Close
Located in Henderson, NV / 2,143 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:
21 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 1C4RJEAG4NC171451
Stock: 27397426
Certified Pre-Owned: No - New Listing$27,990good price$2,373 below market
- 30,394 miles
- 5 Seats, 18 City / 25 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Richmond, VA / 100 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:
21 Combined MPG (18 City/25 Highway)
Listing Information:
VIN: 1C4RJFBG1NC140744
Stock: 2003590974
Certified Pre-Owned: No
Listed since: 03-22-2025 - New Listing
- 16,371 miles
- No accidents, 1 owner, personal use
- 5 Seats, 18 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from TN to VA*
Close
Located in Jackson, TN / 708 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: 1C4RJFBG7NC122636
Stock: 27327534
Certified Pre-Owned: No - New Listing$29,990fair price
- 21,869 miles
- No accidents, 2 owners, personal use
- 5 Seats, 19 City / 26 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in San Antonio, TX / 1,380 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:
21 Combined MPG (19 City/26 Highway)
Listing Information:
VIN: 1C4RJEBG8NC153906
Stock: 2003635360
Certified Pre-Owned: No
Listed since: 05-18-2025 - New Listing$27,998fair price$62 above market
- 53,607 miles
- 5 Seats, 18 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from Midlothian, VA*
Close
Located in Midlothian, VA / 93 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:
21 Combined MPG (18 City/25 Highway)
Listing Information:
VIN: 1C4RJFAG5NC118182
Stock: 26607228
Certified Pre-Owned: No - Price Drop$30,590fair price$379 above market
- 26,491 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 25 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Indianapolis, IN / 579 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: 1C4RJFBG1NC146639
Stock: 2003719529
Certified Pre-Owned: No
Listed since: 05-15-2025 - Price Drop$24,590fair price$637 above market
- 54,687 miles
- No accidents, 1 owner, corporate fleet vehicle
- 5 Seats, 18 City / 25 Hwy MPG
- Carvana (In-stock online)
- Home delivery*
Close
Located in Philadelphia, PA / 236 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: 1C4RJFAG8NC141469
Stock: 2003696030
Certified Pre-Owned: No
Listed since: 05-14-2025 - 30,034 miles
- No accidents, 2 owners, personal use
- 5 Seats, 18 City / 25 Hwy MPG
- CarMax (In-stock online)
- Transfer available from CA to VA*
Close
Located in Costa Mesa, CA / 2,344 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: 1C4RJFAG3NC163105
Stock: 27383232
Certified Pre-Owned: No
Showing 22 - 42 out of 61 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.
Filters
Skip to ResultsApplied Filters4Active
Make & Model
Year
New / Used
Price & Payments
Price Rating
Body Type
Trim
Mileage
Accidents & History
Engine & Drivetrain
Exterior Color
Interior Color
Total Seating
Edmunds Review
Features
Options & Packages
MPG
* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.