Jeep Gladiator Trucks for Sale near Winchester, Virginia
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Price
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Make, Model, and Trim
Year
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State
Used 2025 Jeep Gladiator Rubicon Crew Cab
$45,790
speed 5,624 mi
sell
Key features
- Gasoline
- 3.6L V6 24V MPFI DOHC
- 4x4
location_on
Hagerstown Ford
Hagerstown, MD (38.3 mi)
(240) 730-4559
Used 2025 Jeep Gladiator Rubicon Crew Cab
$59,999
speed 8,137 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Country Chevrolet - Warrenton
Warrenton, VA (38.9 mi)
Used 2025 Jeep Gladiator Rubicon Crew Cab
$52,999
speed 8,783 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Country Chevrolet - Warrenton
Warrenton, VA (38.9 mi)
Used 2026 Jeep Gladiator Sport Crew Cab
$54,999
speed 5,682 mi
sell
Key features
- Gasoline
- 4WD
- Texas Trail
location_on
Country Chevrolet - Warrenton
Warrenton, VA (38.9 mi)
Used 2026 Jeep Gladiator Mojave Crew Cab
$49,999
speed 163 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Country Chevrolet - Warrenton
Warrenton, VA (38.9 mi)
Used 2024 Jeep Gladiator Sport Crew Cab
$28,777
speed 50,591 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Fair Oaks Chrysler Jeep Dodge Ram
Chantilly, VA (43.4 mi)
(240) 255-9163
Used 2020 Jeep Gladiator Rubicon Crew Cab
$28,299
speed 78,599 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Fair Oaks Chrysler Jeep Dodge Ram
Chantilly, VA (43.4 mi)
(240) 255-9163
Used 2024 Jeep Gladiator Sport Crew Cab
$34,996
speed 10,241 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
DARCARS Chrysler Dodge Jeep Ram of Rockville
Rockville, MD (56.7 mi)
(301) 658-6567
Used 2020 Jeep Gladiator Overland Crew Cab
$35,799
speed 37,874 mi
sell
Key features
- Gasoline
- Regular Unleaded V-6 3.6 L/220
- 4WD
location_on
Len Stoler Dodge Chrysler Jeep
Westminster, MD (69.1 mi)
(443) 201-7403
Used 2022 Jeep Gladiator Overland Crew Cab
$32,299
speed 39,094 mi
sell
Key features
- Diesel
- Intercooled Turbo Diesel V-6 3.0 L/182
- 4WD
location_on
Len Stoler Dodge Chrysler Jeep
Westminster, MD (69.1 mi)
(443) 201-7403
Used 2022 Jeep Gladiator Overland Crew Cab
$29,799
speed 61,333 mi
sell
Key features
- Diesel
- Intercooled Turbo Diesel V-6 3.0 L/182
- 4WD
location_on
Len Stoler Dodge Chrysler Jeep
Westminster, MD (69.1 mi)
(443) 201-7403
Used 2021 Jeep Gladiator Overland Crew Cab
$31,498
speed 39,292 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
Safford Chrysler Dodge Jeep Ram FIAT of Fredericksburg
Fredericksburg, VA (76.4 mi)
(540) 296-2597
Used 2021 Jeep Gladiator Mojave Crew Cab
$32,998
speed 52,984 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Safford Chrysler Dodge Jeep Ram FIAT of Fredericksburg
Fredericksburg, VA (76.4 mi)
(540) 296-2597
Used 2022 Jeep Gladiator Sport Crew Cab
$31,498
speed 36,336 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Safford Chrysler Dodge Jeep Ram FIAT of Fredericksburg
Fredericksburg, VA (76.4 mi)
(540) 296-2597
Used 2022 Jeep Gladiator Rubicon Crew Cab
$36,593
speed 36,962 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Malloy Ford Charlottesville
Charlottesville, VA (77.6 mi)
(434) 252-3083
Used 2020 Jeep Gladiator Rubicon Crew Cab
$33,796
speed 31,395 mi
sell
Key features
- Gasoline
- 4WD
- Rubicon
location_on
Koons Ford Of Annapolis
Annapolis, MD (87.6 mi)
(443) 242-9478
Used 2023 Jeep Gladiator Mojave Crew Cab
$38,800
speed 21,666 mi
sell
Key features
- Gasoline
- 4WD
- Mojave
location_on
Bob Davidson Ford Lincoln
Baltimore, MD (89.2 mi)
(443) 234-9274
Used 2022 Jeep Gladiator Sport Crew Cab
$31,490
speed 25,790 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Fred Beans Ford Mechanicsburg
Mechanicsburg, PA (96.1 mi)
(717) 527-7788
Used 2025 Jeep Gladiator Mojave Crew Cab
$45,942
speed 17,871 mi
sell
Key features
- Gasoline
- 4x4
- Mojave
location_on
Luck Chevrolet
Ashland, VA (104.6 mi)
(804) 589-4709
Used 2023 Jeep Gladiator Sport Crew Cab
$37,350 List Price
$32,039
speed 14,037 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Southern Chrysler Dodge Jeep Ram FIAT Newport News
Newport News, VA (114.7 mi)
(757) 960-7592
Used 2025 Jeep Gladiator High Crew Cab
$40,471
speed 3,084 mi
sell
Key features
- Gasoline
- 4WD
- High Tide
location_on
Southern Chrysler Dodge Jeep Ram FIAT Newport News
Newport News, VA (114.7 mi)
(757) 960-7592
Used 2023 Jeep Gladiator Sport Crew Cab
$26,525
speed 70,473 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Southern Chrysler Dodge Jeep Ram FIAT Newport News
Newport News, VA (114.7 mi)
(757) 960-7592
Used 2024 Jeep Gladiator Sport Crew Cab
$37,575 List Price
$33,980
speed 3,013 mi
sell
Key features
- Gasoline
- 4WD
- Sport S
location_on
Southern Chrysler Dodge Jeep Ram FIAT Newport News
Newport News, VA (114.7 mi)
(757) 960-7592
Used 2020 Jeep Gladiator Sport Crew Cab
$23,449
speed 69,961 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
Klick Lewis Chevrolet
Palmyra, PA (114.9 mi)
Used 2022 Jeep Gladiator Sport Crew Cab
$29,188
speed 50,867 mi
sell
Key features
- Gasoline
- 4WD
- Willys
location_on
Frederick Chevrolet of Lebanon
Lebanon, PA (123.7 mi)
Used 2020 Jeep Gladiator Rubicon Crew Cab
$30,929
speed 52,485 mi
sell
Key features
- Gasoline
- 3.6L V-6 DOHC, variable valve control, regular gasoline, engine with 285HP
- 4WD
location_on
Bowser Buick GMC
Pleasant Hills, PA (125.6 mi)
Used 2025 Jeep Gladiator Mojave Crew Cab
$42,426
speed 23,043 mi
sell
Key features
- Gasoline
- Pentastar 3.6L V-6 DOHC, variable valve control, regular gasoline, engine with 285HP
- 4WD
location_on
Bowser Buick GMC
Pleasant Hills, PA (125.6 mi)
Used 2020 Jeep Gladiator Rubicon Crew Cab
$24,300
speed 110,180 mi
sell
Key features
- Gasoline
- V6 Cylinder Engine
- 4x4
location_on
Preston Ford
Hurlock, MD (129.2 mi)
(443) 673-5103
Used 2020 Jeep Gladiator Overland Crew Cab
$23,485
speed 99,582 mi
sell
Key features
- Gasoline
- 4WD
- Overland
location_on
#1 Cochran Ford of Allegheny Valley
Natrona Heights, PA (130.1 mi)
(878) 879-6229
Used 2025 Jeep Gladiator Sport Crew Cab
$38,747
speed 5,995 mi
sell
Key features
- Gasoline
- 4WD
- Sport
location_on
#1 Cochran Ford of Allegheny Valley
Natrona Heights, PA (130.1 mi)
(878) 879-6229






















































