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391 listings
  • New Listing
    $44,980
    good price
    $3,350 below market
    • 17,010 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Reno, NV / 2,446 miles away from Windsor, CT

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Leather S...

    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: 1C6JJTBG4PL560200
    Stock: PL560200C
    Certified Pre-Owned: Yes

  • Price Drop
    $36,599
    great price
    $5,113 below market
    • 46,465 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Coon Rapids, MN / 1,058 miles away from Windsor, CT

    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:

    19 Combined MPG (16 City/23 Highway)

    Listing Information:

    VIN: 1C6JJTEG3ML608857
    Stock: S8627543A
    Certified Pre-Owned: Yes

  • $39,995
    great price
    $5,501 below market
    • 14,247 miles
    • No accidents, 1 owner, personal use only
    • 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 Washington, MI / 535 miles away from Windsor, CT

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

    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: 1C6JJTEG2ML597415
    Stock: PML597415S
    Certified Pre-Owned: No

  • $29,945
    great price
    $3,490 below market
    • 44,393 miles
    • No accidents, 1 owner, corporate fleet vehicle
    • 5'0” bed, 3.6l, 6cyl
    • Bolles Motors (9 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Ellington, CT / 9 miles away from Windsor, CT

    CARFAX One-Owner. Clean CARFAX. Certified. Silver Zynith Clearcoat 2023 Jeep Gladiator Overland 4WD 8-Speed Automatic 3.6L V6 24V VVT ***4 NEW TIRES**...

    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: 1C6HJTFG1PL531763
    Stock: 904567
    Certified Pre-Owned: Yes
    Listed since: 02-13-2025

  • Price Drop
    $36,990
    great price
    $6,306 below market
    • 13,351 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
    • Leather Seats
    Close

    Located in Sacramento, CA / 2,552 miles away from Windsor, CT

    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: 1C6HJTFG3ML528214
    Stock: 2003674530
    Certified Pre-Owned: No
    Listed since: 04-25-2025

  • $40,941
    fair price
    $1,473 below market
    • 11,097 miles
    • No accidents, 1 owner, personal use only
    • 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 Yuba City, CA / 2,545 miles away from Windsor, CT

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Rare Find,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Leather Seats,Navigation System,...

    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: 1C6JJTEG3PL557607
    Stock: PL557607T
    Certified Pre-Owned: Yes

  • Price Drop
    $34,998
    good price
    $2,123 below market
    • 22,600 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from AL to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Hoover, AL / 971 miles away from Windsor, 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: 1C6JJTBG3ML614680
    Stock: 26584291
    Certified Pre-Owned: No

  • $33,998
    fair price
    $1,435 below market
    • 17,307 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from FL to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Fort Myers, FL / 1,176 miles away from Windsor, 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: 1C6HJTAG6LL173464
    Stock: 27312434
    Certified Pre-Owned: No

  • $32,088
    good price
    $2,663 below market
    • 31,570 miles
    • 1 accident, 1 owner, personal use
    • 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 / 645 miles away from Windsor, CT

    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: 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: 1C6HJTAG9NL136055
    Stock: E11915
    Certified Pre-Owned: No
    Listed since: 04-05-2025

  • New Listing
    $40,998
    good price
    $2,381 below market
    • 11,570 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from WA to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Vancouver, WA / 2,464 miles away from Windsor, 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: 1C6JJTEG9ML605543
    Stock: 27075392
    Certified Pre-Owned: No

  • New Listing
    $35,998
    good price
    $3,099 below market
    • 31,000 miles
    • No accidents, 2 owners, personal use only
    • 5'0” bed, 3l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from GA to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Upgraded Headlights
    • Blind Spot Monitorin...
    Close

    Located in Kennesaw, GA / 846 miles away from Windsor, 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:

    Listing Information:

    VIN: 1C6JJTAM5ML593693
    Stock: 26592574
    Certified Pre-Owned: No

  • New Listing
    $34,998
    fair price
    $1,635 below market
    • 43,497 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from FL to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Orlando, FL / 1,045 miles away from Windsor, 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:

    Listing Information:

    VIN: 1C6JJTFM1NL109187
    Stock: 27184195
    Certified Pre-Owned: No

  • Price Drop
    $40,980
    fair price
    $2,097 below market
    • 16,473 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
    • Upgraded Headlights
    Close

    Located in Reno, NV / 2,446 miles away from Windsor, CT

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Seats,Heated Steerin...

    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: 1C6JJTBG8ML616943
    Stock: ML616943C
    Certified Pre-Owned: Yes

  • Price Drop
    $37,499
    good price
    $3,086 below market
    • 45,451 miles
    • No accidents, 1 owner, personal use only
    • 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 Kennewick, WA / 2,297 miles away from Windsor, CT

    CarFax No Accidents Reported,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Heated Steering Wheel,Keyless Start,Leather Seats,Remo...

    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: 1C6JJTBG7ML500732
    Stock: ML500732A
    Certified Pre-Owned: No

  • $28,499
    good price
    $1,930 below market
    • 48,879 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
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Morgantown, WV / 414 miles away from Windsor, CT

    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 (16 City/23 Highway)

    Listing Information:

    VIN: 1C6HJTAG1PL514940
    Stock: 7VM4W5
    Certified Pre-Owned: No
    Listed since: 04-18-2025

  • New Listing
    $33,998
    fair price
    $1,259 below market
    • 80,965 miles
    • No accidents, 1 owner, personal use only
    • 5'0” bed, 3l, 6cyl
    • CarMax (In-stock online)
    • Transfer available from CA to CT*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in Canoga Park, CA / 2,525 miles away from Windsor, 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:

    Listing Information:

    VIN: 1C6JJTBM8ML592486
    Stock: 27185880
    Certified Pre-Owned: No

  • Price Drop
    $33,338
    good price
    $3,036 below market
    • 39,011 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
    • Leather Seats
    • Keyless Entry/Start
    Close

    Located in Temecula, CA / 2,470 miles away from Windsor, CT

    CarFax No Accidents Reported,CarFax 1-Owner,Rare Find,Back-Up Camera,Blind Spot Monitor,Bluetooth,Brake Assist,Keyless Start,Navigation System,Premium...

    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: 1C6HJTFG0ML525013
    Stock: ML525013P
    Certified Pre-Owned: Yes

  • $42,499
    good price
    $3,151 below market
    • 12,697 miles
    • No accidents, 2 owners, personal use
    • 5'0” bed, 3.6l, 6cyl
    • Gengras Chrysler Dodge Jeep Ram (6 mi away)
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Keyless Entry/Start
    Close

    Located in East Hartford, CT / 6 miles away from Windsor, CT

    Certified. Hydro Blue Pearlcoat 2023 Jeep Gladiator Rubicon 3.6L V6 24V VVT 8-Speed Automatic 4WD CARFAX One-Owner.Odometer is 4713 miles below market...

    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: 1C6JJTBG3PL500036
    Stock: ZR00036
    Certified Pre-Owned: Yes
    Listed since: 05-02-2025

  • Price Drop
    $30,999
    good price
    $2,872 below market
    • 26,048 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
    • Tire Pressure Warnin...
    • USB Inputs
    Close

    Located in Coon Rapids, MN / 1,058 miles away from Windsor, CT

    CarFax No Accidents Reported,CarFax 1-Owner,Low Mileage,Apple CarPlay,Back-Up Camera,Bluetooth,Brake Assist,Keyless Start,Satellite Radio,HD Radio,V6 ...

    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: 1C6HJTAG7ML613709
    Stock: PML613709
    Certified Pre-Owned: Yes

  • New Listing
    $37,954
    fair price
    $2,221 below market
    • 30,007 miles
    • No accidents, 3 owners, personal use only
    • 5'0” bed, 3.6l, 6cyl
    • Driveway (In-stock online)
    • Home delivery*
    • AWD/4WD
    • Back-up camera
    • Bluetooth
    • Navigation
    • Leather Seats
    Close

    Located in Missoula, MT / 2,058 miles away from Windsor, CT

    CarFax No Accidents Reported,Back-Up Camera,Bluetooth,Brake Assist,Heated Seats,Heated Steering Wheel,Keyless Start,Leather Seats,Remote Start,Satelli...

    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: 1C6JJTBG4ML585982
    Stock: 17837
    Certified Pre-Owned: No

  • Price Drop
    $42,491
    fair price
    $922 below market
    • 13,356 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
    • Leather Seats
    Close

    Located in Bellevue, WA / 2,420 miles away from Windsor, CT

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

    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: 1C6JJTEG9PL510341
    Stock: PL510341A
    Certified Pre-Owned: No

Showing 43 - 63 out of 391 listings

Buying a Jeep Gladiator in Windsor Connecticut

The Jeep Gladiator is an exceptional choice for adventurous individuals in Windsor, CT, especially those who enjoy exploring the scenic beauty of local parks and nature trails. Its rugged character and off-road capabilities make it well-suited for tackling the varied terrain found in nearby destinations like the Metacomet Trail or even venturing further into the picturesque landscapes of the Connecticut River Valley. With its convertible design, owners can easily soak up the sun while cruising through town, making it a unique vehicle that stands out among traditional pickups.

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