Skip to main content
Skip to Filters
531 listings
  • $39,875
    good price
    $4,573 below market
    • 8,788 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Valenti Hartford (16 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Blind Spot Monitorin...
    Close

    Located in Hartford, CT / 16 miles away from Middletown, CT

    Granite Crystal Metallic Clear Coat ($245) Trailer Tow Package ($395) Cold Weather Group ($995) 8.4" Radio and Premium Audio Group ($1,995) Jeep Activ...

    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: 1C6JJTBG1ML588273
    Stock: S472
    Certified Pre-Owned: No
    Listed since: 08-04-2025

  • Price Drop
    $18,995
    great price
    $2,711 below market
    • 111,064 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • A Better Way Wholesale Autos (19 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Naugatuck, CT / 19 miles away from Middletown, CT

    - Rugged yet refined, the 2020 Jeep Gladiator Sport offers a powerful 3.6L V6 engine with 285 horsepower and 260 ft-lbs of torque. - Enjoy adventure-...

    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: 1C6JJTAG5LL127979
    Stock: 127979N
    Certified Pre-Owned: No

  • Price Drop
    $27,895
    good price
    $2,642 below market
    • 58,952 miles
    • No accidents, 1 owner, rental vehicle
    • 5'0” bed, 3.6l, 6cyl
    • The Highline Car Connection (22 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Waterbury, CT / 22 miles away from Middletown, CT

    Silver Zynith Clearcoat 2023 Jeep Gladiator Sport 4WD 8-Speed Automatic 3.6L V6 24V VVT.....We Have Been In Business SINCE 1988. CELEBRATING 35 YEAR...

    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:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG8PL520055
    Stock: 520055
    Certified Pre-Owned: No
    Listed since: 08-27-2025

  • $36,994
    fair price
    $2,239 below market
    • 49,235 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3l, 6cyl
    • Branhaven Chrysler Jeep Dodge Ram (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Branford, CT / 21 miles away from Middletown, CT

    2021 Jeep Gladiator Overland ***CHRYSLER PRE OWNED CERTIFIED***, ***CLEAN CAR FAX***, ***1 OWNER***, DUAL TOP GROUP, MANY EXTRAS, Gladiator Overland, ...

    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: 1C6JJTFM9ML585511
    Stock: 27061
    Certified Pre-Owned: Yes
    Listed since: 08-26-2025

  • $37,869
    good price
    $1,801 below market
    • 34,869 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Madison Chrysler Jeep Dodge Ram (19 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Madison, CT / 19 miles away from Middletown, CT

    2022 Jeep Gladiator Mojave One Owner Trade In, Jeep certified till 12/27/28 or up to 100k miles! 240 Amp Alternator, Apple CarPlay/Android Auto, Class...

    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: 1C6JJTEG4NL101256
    Stock: P1346
    Certified Pre-Owned: Yes
    Listed since: 07-02-2025

  • $29,998
    good price
    $1,210 below market
    • 31,461 miles
    • No accidents, 2 owners, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • CarMax East Haven (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in East Haven, CT / 21 miles away from Middletown, CT

    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: Yes

    Features and Specs:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG2NL109070
    Stock: 27576174
    Certified Pre-Owned: No

  • New Listing
    $32,947
    fair price
    $435 below market
    • 16,842 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Northwest Hills Chevrolet Buick GMC (28 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Torrington, CT / 28 miles away from Middletown, CT

    2021 Jeep Gladiator Willys**Certified**, **Clean Carfax**, **4 Wheel Drive**, Bluetooth Phone/Audio, **Apple car play / Android Auto**, Gladiator Will...

    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: 1C6HJTAG8ML614917
    Stock: X25-536A
    Certified Pre-Owned: No
    Listed since: 09-06-2025

  • $24,495
    good price
    $2,394 below market
    • 93,401 miles
    • 1 accident, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Riverhead Chrysler Dodge Jeep Ram (43 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Riverhead, NY / 43 miles away from Middletown, CT

    Vehicle DetailsGet ready to conquer the road and redefine your driving experience with this rugged and versatile 2020 Jeep Gladiator Sport S! ...

    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: 1C6JJTAG6LL138540
    Stock: UR1617
    Certified Pre-Owned: No
    Listed since: 08-21-2025

  • $36,748
    fair price
    $241 above market
    • 19,077 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Branhaven Chrysler Jeep Dodge Ram (21 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Keyless Entry/Start
    • Tire Pressure Warnin...
    Close

    Located in Branford, CT / 21 miles away from Middletown, CT

    2022 Jeep Gladiator WillysOdometer is 12340 miles below market average!Jeep Combined Details: * Vehicle History * Powertrain Limited 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: 1C6HJTAG8NL179012
    Stock: 27064
    Certified Pre-Owned: Yes
    Listed since: 08-26-2025

  • $35,495
    good price
    $2,401 below market
    • 36,017 miles
    • 1 accident, 1 owner, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Harte Volkswagen Of Meriden (8 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Meriden, CT / 8 miles away from Middletown, CT

    2021 Odometer is 6842 miles below market average! Jeep Gladiator High Altitude 8-Speed Automatic 17/22 City/Highway MPGWe make buying cars easy! Outst...

    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: 1C6HJTFG6ML555939
    Stock: VW2555
    Certified Pre-Owned: No
    Listed since: 06-25-2025

    • 75,035 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Toyota of Colchester (17 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Colchester, CT / 17 miles away from Middletown, CT

    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: 1C6HJTAG1LL177924
    Stock: 20184A
    Certified Pre-Owned: No
    Listed since: 06-06-2025

  • New Listing
    • 34,681 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Ingersoll Auto of Danbury (41 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Danbury, CT / 41 miles away from Middletown, CT

    Priced below KBB Fair Purchase Price! Odometer is 1030 miles below market average! Clean CARFAX.Front dual zone A/C, ParkView Rear Back-Up Camera, R...

    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: 1C6JJTEG0ML565546
    Stock: P565546
    Certified Pre-Owned: No
    Listed since: 09-05-2025

  • Price Drop
    • 36,198 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • McGee Toyota of Putnam (48 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • Upgraded Stereo
    Close

    Located in Putnam, CT / 48 miles away from Middletown, CT

    McGee Toyota of Putnam is proud to present you with this 2021 Jeep Gladiator Overland! ---------- ONE (1) OWNER TRADE-IN, 4WD, 3.6L V-6 ENGINE, 8...

    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: 1C6HJTFG0ML610921
    Stock: P3402
    Certified Pre-Owned: No
    Listed since: 08-25-2025

  • New Listing
    Stock photo**
    $34,900
    fair price
    $329 above market
    • 32,542 miles
    • 5'0” bed, 3.6l, 6cyl
    • Riverhead Chrysler Dodge Jeep Ram (43 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Riverhead, NY / 43 miles away from Middletown, CT

    Vehicle Details2021 Jeep Gladiator Overland — 32,542 miles — Riverhead, NY This 2021 Jeep Gladiator Overland is a rugged yet refined midsize ...

    AutoCheck Vehicle History Summary Unavailable.

    Features and Specs:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTFG2ML618065
    Stock: UR1654
    Certified Pre-Owned: No
    Listed since: 09-18-2025

  • $31,995
    fair price
    $998 below market
    • 62,151 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • J&M Automotive (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Naugatuck, CT / 20 miles away from Middletown, CT

    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: 1C6HJTFG1ML512481
    Stock: 2112481
    Certified Pre-Owned: No

  • New Listing
    • 61,842 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • The Highline Car Connection (22 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Waterbury, CT / 22 miles away from Middletown, CT

    Bright White Clearcoat 2023 Jeep Gladiator Overland 4WD 8-Speed Automatic 3.6L V6 24V VVT.....We Have Been In Business SINCE 1988. CELEBRATING 35 YE...

    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: 1C6HJTFG8PL539634
    Stock: 539634
    Certified Pre-Owned: No
    Listed since: 09-17-2025

  • $25,995
    fair price
    $888 below market
    • 80,045 miles
    • 1 accident, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • J&M Automotive (20 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Naugatuck, CT / 20 miles away from Middletown, CT

    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: 1C6HJTAG2ML589660
    Stock: 2189660
    Certified Pre-Owned: No

  • $36,500
    great price
    $6,315 below market
    • 27,124 miles
    • No accidents, 4 owners, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Temecula, CA / 2,469 miles away from Middletown, CT

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

    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: 1C6JJTBGXML545910
    Stock: ML545910P
    Certified Pre-Owned: No

  • $45,998
    great price
    $5,857 below market
    • 7,057 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from KS to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Wichita, KS / 1,329 miles away from Middletown, CT

    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:

    18 Combined MPG (16 City/21 Highway)

    Listing Information:

    VIN: 1C6JJTEG4RL107726
    Stock: 27490390
    Certified Pre-Owned: No

    • 33,535 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from TX to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Blind Spot Monitorin...
    • Tire Pressure Warnin...
    Close

    Located in Lubbock, TX / 1,688 miles away from Middletown, CT

    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: 1C6HJTAGXML620363
    Stock: 27178859
    Certified Pre-Owned: No

  • Price Drop
    $34,489
    great price
    $4,174 below market
    • 19,230 miles
    • No accidents, 1 owner, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Springfield, VA / 306 miles away from Middletown, CT

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless...

    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: 1C6HJTAG1NL170586
    Stock: NL170586P
    Certified Pre-Owned: No

Showing 1 - 21 out of 531 listings
Filters
Skip to Results

Applied Filters4Active

Select Buying Experience

Location

Search radius50 miles
Search radius

Make & Model

Year

New / Used

Price & Payments

Price Rating

Trim

Truck Details

Mileage

Accidents & History

Engine & Drivetrain

Exterior Color

Interior Color

Total Seating

Edmunds Review

Features

Options & Packages

MPG

Listing Details


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