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815 listings
  • Price Drop
    $28,999
    fair price
    $218 above market
    • 67,000 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Saint Louis, MO / 782 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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG3PL523583
    Stock: 7VR6Q2
    Certified Pre-Owned: No
    Listed since: 05-09-2025

  • Price Drop
    Stock photo**
    $34,995
    good price
    $1,736 below market
    • 46,216 miles
    • 1 accident, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Nissan of Richmond (99 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Richmond, VA / 99 miles away from Chesapeake, VA

    Built for life's adventures, this vehicle offers the versality you need with the style you deserve.Recent Arrival! 2023 Jeep Gladiator High AltitudeOu...

    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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG0PL533858
    Stock: P7187
    Certified Pre-Owned: No
    Listed since: 07-03-2025

  • Price Drop
    • 28,554 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Sport Chevrolet (167 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Blind Spot Monitorin...
    • Tire Pressure Warnin...
    Close

    Located in Silver Spring, MD / 167 miles away from Chesapeake, VA

    CHECK OUT ALL THESE GREAT OPTIONS Quick Order Package 23D, Safety Group (Blind Spot & Cross Path Detection and ParkSense Rear Park Assist System), Tra...

    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: 1C6JJTEG2ML559859
    Stock: ML559859
    Certified Pre-Owned: No
    Listed since: 05-24-2025

  • New Listing
    Stock photo**
    $31,399
    fair price
    $688 above market
    • 33,534 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Bleecker Chevrolet (165 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    Located in Dunn, NC / 165 miles away from Chesapeake, VA

    4x4, Smart Device Integration, Brake Actuated Limited Slip Differential, WiFi Hotspot, Apple CarPlay , Onboard Communications System, iPod/MP3 Input,...

    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: 1C6HJTAG4PL548340
    Stock: 25117A
    Certified Pre-Owned: No
    Listed since: 07-02-2025

    • 408 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    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: 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: 1C6JJTEG4PL580636
    Stock: 2003863874
    Certified Pre-Owned: No
    Listed since: 07-10-2025

    • 6,499 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from CA to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Ontario, CA / 2,317 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:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG3PL576730
    Stock: 27089358
    Certified Pre-Owned: No

    • 10,485 miles
    • No accidents, 2 owners, personal use
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from GA to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Gainsville, GA / 462 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: 1C6JJTEG3PL560040
    Stock: 27488969
    Certified Pre-Owned: No

    • 12,349 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from NV to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Las Vegas, NV / 2,152 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: 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: 1C6JJTEGXPL530310
    Stock: 27263707
    Certified Pre-Owned: No

  • New Listing
    Stock photo**
    $30,903
    fair price
    $999 above market
    • 46,182 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Westgate Triad Mitsubishi (182 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Graham, NC / 182 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:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG0PL523735
    Stock: 3787P
    Certified Pre-Owned: No
    Listed since: 04-05-2025

    • 16,953 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from CA to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in San Diego, CA / 2,321 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: 1C6JJTBG9PL563450
    Stock: 26850734
    Certified Pre-Owned: No

  • $36,988
    great price
    $8,485 below market
    • 3,734 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Jake Sweeney Express (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Cincinnati, OH / 482 miles away from Chesapeake, VA

    Jake Sweeney Is the only Chrysler Dodge Jeep Ram dealer in the Cincinnati metro area to offer a complementary Lifetime Mechanical Protection with a $0...

    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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: 1C6HJTAG8RL115817
    Stock: E11989
    Certified Pre-Owned: No
    Listed since: 06-16-2025

  • New Listing
    $33,590
    fair price
    $1,170 above market
    • 18,577 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Cincinnati, OH / 480 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: 1C6HJTAG7PL538773
    Stock: 2003799578
    Certified Pre-Owned: No
    Listed since: 06-18-2025

  • New Listing
    $30,590
    fair price
    $92 below market
    • 44,416 miles
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    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 Unavailable.

    Features and Specs:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG3PL532680
    Stock: 2003868946
    Certified Pre-Owned: No
    Listed since: 07-09-2025

  • New Listing
    $32,990
    fair price
    $4 above market
    • 41,985 miles
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    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 Unavailable.

    Features and Specs:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG8PL532201
    Stock: 2003823478
    Certified Pre-Owned: No
    Listed since: 07-15-2025

  • New Listing
    $29,590
    fair price
    $377 below market
    • 52,498 miles
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Tampa, FL / 707 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:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG0PL528716
    Stock: 2003864537
    Certified Pre-Owned: No
    Listed since: 07-11-2025

  • New Listing
    $30,398
    fair price
    $561 below market
    • 62,833 miles
    • 5'0” bed, 3.6l, 6cyl
    • Enterprise Car Sales (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Madison, TN / 582 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 Unavailable.

    Features and Specs:

    19 Combined MPG (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTFG3PL522529
    Stock: 7VQ3Q9
    Certified Pre-Owned: No
    Listed since: 07-08-2025

    • 27,129 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Carvana - Richmond (100 mi away)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    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

    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: 1C6HJTFG8ML557398
    Stock: 2003876543
    Certified Pre-Owned: No
    Listed since: 07-10-2025

    • 40,147 miles
    • 2 accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • INFINITI of Wilmington (194 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Tire Pressure Warnin...
    Close

    Located in Wilmington, NC / 194 miles away from Chesapeake, VA

    Bluetooth, Backup Camera, AndroidTM Auto/Apple Carplay, Heated/Cooled Seats.Priced below KBB Fair Purchase Price!2021 Jeep Gladiator Overland Sarge...

    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: 1C6HJTFG7ML573303
    Stock: 2000026C
    Certified Pre-Owned: No
    Listed since: 06-04-2025

    • 18,690 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from CO to VA*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Loveland, CO / 1,567 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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTAGXPL588602
    Stock: 27243598
    Certified Pre-Owned: No

    • 22,230 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Carvana (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Upgraded Headlights
    Close

    Located in Oklahoma City, OK / 1,189 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 (17 City/22 Highway)

    Listing Information:

    VIN: 1C6HJTAG6PL519485
    Stock: 2003855236
    Certified Pre-Owned: No
    Listed since: 06-30-2025

  • New Listing
    • 30,200 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3l, 6cyl
    • John Hiester Chevrolet (159 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Fuquay Varina, NC / 159 miles away from Chesapeake, VA

    Granite Crystal Metallic Clearcoat 2023 Jeep Gladiator Willys 4WD 8-Speed Automatic 3.0L V6 TurbodieselONE OWNER ACCIDENT FREE CARFAX, LIFETIME ENGINE...

    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:

    Listing Information:

    VIN: 1C6JJTAM9PL594852
    Stock: 9440A
    Certified Pre-Owned: No
    Listed since: 07-01-2025

Showing 232 - 252 out of 815 listings

Consumer Reviews for the Jeep Gladiator

Read recent reviews for the Jeep Gladiator
Overall Consumer Rating
4.1 out of 5 stars38 Reviews
Write a vehicle reviewSee all 38 reviews
  • 5 star
    (68%)
  • 4 star
    (11%)
  • 3 star
    (0%)
  • 2 star
    (5%)
  • 1 star
    (16%)
5 out of 5 stars

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!
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Used 2023 Jeep Gladiator in Chesapeake, VA Values

Estimated values
2023 Jeep Gladiator Overland 4dr Crew Cab 4WD SB (3.6L 6cyl 8A) with no options
ConditionTrade-InPrivate PartyDealer Retail
Outstanding$26,830$28,525$30,436
Clean$26,526$28,181$30,046
Average$26,021$27,607$29,396
Rough$25,364$26,862$28,551

The average list price of a used 2023 Jeep Gladiator in Chesapeake, Virginia is $35,972. The average mileage on a used Jeep Gladiator 2023 for sale in Chesapeake, Virginia is 30,029. Based on the average mileage of 30,029 for used 2023 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 2023 in Chesapeake, Virginia to be $26,021.

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