Used Jeep Cars in Winchester, KY For Sale Under $50,000 (70 results)

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2024 Jeep Grand Cherokee

Discover the 2024 Jeep Grand Cherokee, a robust 4WD SUV with automatic transmission, perfect for both city driving and off-road adventures

automatic

gasoline

Winchester, KY

$48,675

2023 Jeep Grand Cherokee

Explore the rugged capabilities of this 2023 Jeep Grand Cherokee. With a powerful 4WD drive system and an automatic transmission, this SUV is ready for any adventure in and around Winchester

automatic

gasoline

Winchester, KY

$47,988

2025 Jeep Grand Cherokee

Experience the rugged elegance of the 2025 Jeep Grand Cherokee, equipped with an automatic transmission and 4WD, perfect for your adventures

automatic

gasoline

Winchester, KY

$47,675

2024 Jeep Grand Cherokee

Experience luxury and capability with the 2024 Jeep Grand Cherokee, featuring advanced 4WD technology and a smooth automatic transmission for an unparalleled driving experience

automatic

gasoline

Winchester, KY

$47,595

2025 Jeep Grand Cherokee

Experience the rugged elegance of the 2025 Jeep Grand Cherokee, featuring advanced 4WD and smooth automatic transmission, perfect for both on-road and off-road adventures

automatic

gasoline

Winchester, KY

$47,090

2025 Jeep Grand Cherokee

This 2025 Jeep Grand Cherokee, featuring a 4WD system, is equipped with an automatic transmission for seamless driving. Perfect for adventurers seeking comfort and capability

automatic

gasoline

Winchester, KY

$47,080

2024 Jeep Gladiator

Discover the 2024 Jeep Gladiator, a rugged and versatile vehicle designed for adventure with its efficient 4WD system and smooth automatic transmission. Perfect for conquering any terrain from the city to the backcountry

automatic

gasoline

Winchester, KY

$47,055

2025 Jeep Grand Cherokee

This 2025 Jeep Grand Cherokee is equipped with a powerful 4WD drivetrain and an automatic transmission, perfect for tackling all terrains

automatic

gasoline

Winchester, KY

$46,495

2025 Jeep Grand Cherokee

Take on new adventures with this 2025 Jeep Grand Cherokee equipped with 4WD and an automatic transmission, ready to conquer any terrain

automatic

gasoline

Winchester, KY

$43,970

2025 Jeep Grand Cherokee

Explore the road in style with this 2025 Jeep Grand Cherokee. Equipped with 4WD and automatic transmission, this vehicle combines power and comfort for an exceptional driving experience

automatic

gasoline

Winchester, KY

$43,970

2025 Jeep Grand Cherokee

Discover the 2025 Jeep Grand Cherokee, equipped for adventure with 4WD and an automatic transmission, perfect for navigating both city streets and rugged trails

automatic

gasoline

Winchester, KY

$43,970

2025 Jeep Grand Cherokee

Explore the rugged terrain with this 2025 Jeep Grand Cherokee, available with 4WD and automatic transmission for a robust driving experience

automatic

gasoline

Winchester, KY

$43,970

2025 Jeep Grand Cherokee

Discover the power and luxury of the 2025 Jeep Grand Cherokee. This 4WD beauty combines advanced technology and rugged capability for an unforgettable driving experience

automatic

gasoline

Winchester, KY

$43,375

2025 Jeep Grand Cherokee

This 2025 Jeep Grand Cherokee offers robust 4WD capabilities and a smooth automatic transmission, perfect for both off-road adventures and everyday driving

automatic

gasoline

Winchester, KY

$41,425

2021 jeep gladiator rubicon

Take on any adventure with this 2021 Jeep Gladiator Rubicon. Equipped with a powerful 240 Amp alternator, automatic climate control, and a rugged 3-piece hard top, it promises comfort and durability on all terrains

27,664 mi.

Bright white clearcoat

automatic

gasoline

Winchester, KY

$39,988

2021 Jeep Wrangler

This 2021 Jeep Wrangler features an Automatic Transmission and robust 4WD, perfect for off-road adventures. Take on any terrain confidently!

automatic

plug-in hybrid

Winchester, KY

$37,988

2023 jeep wrangler willys

This 2023 Jeep Wrangler Willys in White Knuckle Clearcoat offers a clean CARFAX and one-owner history with low mileage. Enjoy the benefits of Rod Hatfield's trade and finance assist programs for a comprehensive buying experience

22,850 mi.

White

automatic

gasoline

Winchester, KY

$37,988

2021 jeep gladiator rubicon

Discover adventure with this 2021 Jeep Gladiator Rubicon. Featuring a striking Nacho Clearcoat exterior and packed with premium features, it's designed for both comfort and performance on and off the road

46,392 mi.

Nacho clearcoat

automatic

gasoline

Winchester, KY

$37,988

2025 Jeep Compass

Discover the new 2025 Jeep Compass, an adventurous SUV ready for all your journeys with its 4WD capability and smooth automatic transmission

automatic

gasoline

Winchester, KY

$37,710

2024 jeep gladiator sport

This 2024 Jeep Gladiator Sport in Black Clearcoat offers a modern touch with a 12.3'' Touchscreen Display, 4G LTE hotspot, and a suite of smart features. Enjoy both rugged capabilities and comfort features like heated seats and advanced audio systems

12 mi.

Black

automatic

gasoline

Winchester, KY

$37,540

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