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825 listings
- $31,168fair price$179 below market
- 53,478 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Bend, OR / 2,392 miles away from Chesapeake, VA
CarFax No Accidents Reported,Apple CarPlay,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,T...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG7LL146659
Stock: LL146659J
Certified Pre-Owned: No - Price Drop$25,655good price$2,347 below market
- 97,763 miles
- No accidents, 3 owners, personal use only
- 5'0” bed, 3.6l, 6cyl
- Fred Anderson Toyota of Sanford (185 mi away)
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Located in Sanford, NC / 185 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFGXLL216745
Stock: R6272911R
Certified Pre-Owned: No
Listed since: 04-26-2025 - Price Drop$27,995good price$3,830 below market
- 83,564 miles
- No accidents, 1 owner, personal use
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wappingers Falls, NY / 358 miles away from Chesapeake, VA
CarFax No Accidents Reported,CarFax 1-Owner,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Remote Start,Satell...
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/23 Highway)
Listing Information:
VIN: 1C6JJTBG7LL202020
Stock: 620451T
Certified Pre-Owned: No - Price Drop$25,590fair price$834 below market
- 119,458 miles
- No accidents, 2 owners, rental vehicle
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Kansas City, MO / 1,011 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFGXLL174934
Stock: 2003801505
Certified Pre-Owned: No
Listed since: 06-07-2025 - $24,990good price$1,773 below market
- 80,525 miles
- No accidents, 2 owners, rental vehicle
- 5'0” bed, 3.6l, 6cyl
- Apex Car & Truck Sales (161 mi away)
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Located in Apex, NC / 161 miles away from Chesapeake, VA
GORGEOUS LIKE NEW GLADIATIOR! This is a must see great looking excellent condition very versatile 2020 Jeep Gladiator Sport 4WD loaded with goodies an...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG8LL190265
Stock: 190265
Certified Pre-Owned: No
Listed since: 07-09-2025 - New Listing$34,999good price$2,635 below market
- 23,162 miles
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Seattle, WA / 2,438 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 Unavailable.
Features and Specs:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG9LL194826
Stock: L194826CB
Certified Pre-Owned: No - $28,498good price$1,374 below market
- 30,420 miles
- No accidents, 3 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Wexford, PA / 339 miles away from Chesapeake, VA
CarFax No Accidents Reported,Low Mileage,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Premium ...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAGXLL189053
Stock: V189053P
Certified Pre-Owned: No - New Listing$29,990good price$2,371 below market
- 34,068 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Seattle, WA / 2,434 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG0LL188137
Stock: 2003792369
Certified Pre-Owned: No
Listed since: 07-03-2025 - $30,867good price$1,800 below market
- 31,356 miles
- No accidents, 2 owners, personal use
- 5'0” bed, 3.6l, 6cyl
- Doug Henry Buick GMC (134 mi away)
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Located in Goldsboro, NC / 134 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG4LL212738
Stock: K5793A
Certified Pre-Owned: No
Listed since: 01-30-2025 
Photos not available$31,188good price$2,607 below market- 37,716 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Pearson Chrysler Jeep Dodge Ram (95 mi away)
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Located in Richmond, VA / 95 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG7LL166328
Stock: 6463A
Certified Pre-Owned: No
Listed since: 07-16-2025- $26,995good price$1,679 below market
- 81,045 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Westgate Chrysler Dodge Jeep Ram of Burgaw (179 mi away)
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Located in Burgaw, NC / 179 miles away from Chesapeake, VA
The 2020 Jeep Gladiator Overland is the ultimate mashuppart rugged Wrangler, part capable pickup. With its open-air freedom, 4x4 brawn, and bold styli...
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/23 Highway)
Listing Information:
VIN: 1C6HJTFG6LL122233
Stock: 2517XP
Certified Pre-Owned: No
Listed since: 01-11-2025 - $29,590fair price
- 81,713 miles
- No accidents, 2 owners, personal use
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Dallas, TX / 1,195 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTFG8LL107006
Stock: 2003813703
Certified Pre-Owned: No
Listed since: 06-17-2025 - Price Drop$30,000fair price$383 below market
- 45,247 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Back Roads Automotive (1 mi away)
Close
Located in Chesapeake, VA / 1 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG5LL213971
Stock: 34268BR
Certified Pre-Owned: No
Listed since: 02-08-2025 - New Listing$20,515good price$1,958 below market
- 156,733 miles
- 1 accident, 1 owner, personal use
- 5'0” bed, 3.6l, 6cyl
- Criswell Chrysler Dodge Jeep Ram of Woodstock (194 mi away)
Close
Located in Woodstock, VA / 194 miles away from Chesapeake, VA
2020 Jeep Gladiator Sport 4D Crew Cab Firecracker Red Clearcoat 4WD 3.6L V6 24V VVT 8-Speed Automatic240 Amp Alternator, Automatic Headlamps, Class IV...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG7LL125195
Stock: G240231A
Certified Pre-Owned: No
Listed since: 04-30-2025 - $33,415fair price$1,346 below market
- 34,901 miles
- No accidents, 3 owners, personal use only
- 5'0” bed, 3.6l, 6cyl
- Sport Durst Mitsubishi (162 mi away)
Close
Located in Durham, NC / 162 miles away from Chesapeake, VA
Recent Arrival! Clean CARFAX. 2020 Jeep Gladiator Overland 4WD Black Clearcoat 4WD 8-Speed Automatic 3.6L V6 24V VVT *REMAINDER OF FACTORY WARRANTY*, ...
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/23 Highway)
Listing Information:
VIN: 1C6HJTFG2LL173048
Stock: P18038
Certified Pre-Owned: No
Listed since: 07-16-2025 - $28,999fair price$897 above market
- 61,460 miles
- No accidents, 2 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Driveway (In-stock online)
- Home delivery*
Close
Located in Klamath Falls, OR / 2,425 miles away from Chesapeake, VA
CarFax No Accidents Reported,Rare Find,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Tow Hitch,4-Wheel Disc B...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG0LL123496
Stock: LL123496P
Certified Pre-Owned: No - $37,990fair price$1,733 below market
- 49,816 miles
- No accidents, 2 owners, personal use
- 5'0” bed, 3.6l, 6cyl
- Carvana (In-stock online)
- Home delivery*
Close
Located in Charlotte, NC / 277 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBG6LL191348
Stock: 2003867018
Certified Pre-Owned: No
Listed since: 07-15-2025 - Price Drop$31,000fair price$1,623 below market
- 77,469 miles
- No accidents, 1 owner, personal use only
- 5'0” bed, 3.6l, 6cyl
- Buick GMC of Brandywine (139 mi away)
Close
Located in Brandywine, MD / 139 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBG0LL217748
Stock: 294460A
Certified Pre-Owned: No
Listed since: 05-25-2025 - Price Drop$29,998fair price$1,507 below market
- 45,883 miles
- No accidents, 1 owner, personal use
- 5'0” bed, 3.6l, 6cyl
- CarMax (In-stock online)
- Transfer available from TN to VA*
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Located in Bristol, TN / 334 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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6HJTAG1LL213031
Stock: 27565616
Certified Pre-Owned: No - $34,663fair price$608 below market
- 52,949 miles
- No accidents, 2 owners, personal use only
- 5'0” bed, 3.6l, 6cyl
- Winegardner Buick GMC of Prince Frederick (128 mi away)
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Located in Prince Frederick, MD / 128 miles away from Chesapeake, VA
Heated Leather Seats, Dual Zone A/C, CD Player, iPod/MP3 Input, 4x4, Alloy Wheels, Bed Liner, Tow Hitch, SPRAY IN BEDLINER, REMOTE START SYSTEM, ENGIN...
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/23 Highway)
Listing Information:
VIN: 1C6JJTBG0LL145630
Stock: G24450A
Certified Pre-Owned: No
Listed since: 06-12-2025 - $35,995fair price$1,537 below market
- 54,409 miles
- No accidents, 3 owners, corporate fleet vehicle
- 5'0” bed, 3.6l, 6cyl
- Auto Network of Wilmington (194 mi away)
Close
Located in Wilmington, NC / 194 miles away from Chesapeake, VA
ANOTHER CLEAN CARFAX WELL MAINTAINED LOADED UP 4X4 JEEP GLADIATOR RUBICON !!! 2020 JEEP GLADIATOR RUBICON This rugged 4X4 pickup is powered by a re...
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:
19 Combined MPG (16 City/23 Highway)
Listing Information:
VIN: 1C6JJTBG8LL183249
Stock: AS-340A
Certified Pre-Owned: No
Listed since: 07-15-2025
Showing 715 - 735 out of 825 listings
Consumer Reviews for the Jeep Gladiator
Read recent reviews for the Jeep Gladiator
Perfect for me
Dan Hirvi, 04/22/2022
2022 Jeep Gladiator Sport S 4dr Crew Cab 4WD SB (3.6L 6cyl 6M)
I highly recommend the Sport S with the Max Tow Package. Torquey and smooth, the automatic 8-speed transmission is pretty nice with the trusty 3.6 L V6. It's a real hauler or puller when I need it, it's articulation is great for some off road adventures and is comfortable on the highway. Plus, the sticker on my door has a rated payload of 1465 lbs! Don't let them tell you it's not "Jeep" … enough or it's not "truck" enough or it's not comfy enough. Get the customer preferred package with hard top and stick with the M+S rated all terrains for smooth and quiet daily driving. This is a perfect niche vehicle for some people!
Used 2020 Jeep Gladiator in Chesapeake, VA Values
Estimated values
2020 Jeep Gladiator Sport S 4dr Crew Cab 4WD SB (3.6L 6cyl 8A) with no options
| Condition | Trade-In | Private Party | Dealer Retail |
|---|---|---|---|
| Outstanding | $21,664 | $23,987 | $26,232 |
| Clean | $21,267 | $23,527 | $25,706 |
| Average | $20,606 | $22,760 | $24,829 |
| Rough | $19,748 | $21,764 | $23,690 |
The average list price of a used 2020 Jeep Gladiator in Chesapeake, Virginia is $30,005. The average mileage on a used Jeep Gladiator 2020 for sale in Chesapeake, Virginia is 63,483. Based on the average mileage of 63,483 for used 2020 Jeep Gladiator 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 Jeep Gladiator 2020 in Chesapeake, Virginia to be $20,606.
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* Delivery of any kind does not apply to Alaska and Hawaii. Contact the dealer for delivery details, restrictions and costs.