Used Jeep Grand Cherokee in Winchester, VA For Sale Under $60,000 (82 results)

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Winchester, VA

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2025 Jeep Grand Cherokee

Explore the rugged terrain with this 2025 Jeep Grand Cherokee, featuring a powerful 4WD system and smooth automatic transmission, ensuring a comfortable and adventurous ride

automatic

gasoline

Winchester, VA

$59,335

2025 Jeep Grand Cherokee

Discover the 2025 Jeep Grand Cherokee, a powerful and capable 4WD vehicle featuring automatic transmission, ideal for both on and off-road adventures

automatic

gasoline

Winchester, VA

$59,335

2025 Jeep Grand Cherokee

This 2025 Jeep Grand Cherokee offers a robust 4WD capability and a smooth automatic transmission, perfect for any adventure while being comfortable and stylish

automatic

gasoline

Winchester, VA

$59,335

2025 Jeep Grand Cherokee

Discover the versatile 2025 Jeep Grand Cherokee, equipped with a robust 4WD system and an advanced automatic transmission, perfect for both urban and off-road adventures

automatic

gasoline

Winchester, VA

$59,235

2025 Jeep Grand Cherokee

Discover the powerful 2025 Jeep Grand Cherokee, designed for off-road adventures with its robust 4WD capabilities and smooth automatic transmission, perfect for any terrain

automatic

gasoline

Winchester, VA

$59,235

2025 Jeep Grand Cherokee

Introducing the new 2025 Jeep Grand Cherokee—an impressive 4WD SUV offering advanced automatic transmission and cutting-edge features designed for adventure

automatic

gasoline

Winchester, VA

$59,235

2025 Jeep Grand Cherokee

Experience the 2025 Jeep Grand Cherokee, designed for adventure with its robust 4WD system and smooth automatic transmission, perfect for both city driving and off-road excursions

automatic

gasoline

Winchester, VA

$59,235

2025 Jeep Grand Cherokee

Discover the power and luxury of the 2025 Jeep Grand Cherokee, equipped with a robust 4WD system for adventurous driving in any condition

automatic

gasoline

Winchester, VA

$58,740

2025 Jeep Grand Cherokee

This 2025 Jeep Grand Cherokee offers an impressive combination of luxury and capability with its advanced 4WD system and automatic transmission, making it perfect for any adventure

automatic

gasoline

Winchester, VA

$57,235

2025 Jeep Grand Cherokee

Introducing the 2025 Jeep Grand Cherokee, a robust SUV with 4WD, perfect for adventurous drives. Enjoy the ease of an automatic transmission in both daily commutes and off-road escapades

automatic

gasoline

Winchester, VA

$56,640

2024 Jeep Grand Cherokee

Discover the rugged elegance of the 2024 Jeep Grand Cherokee, equipped with advanced 4WD for superior handling and an automatic transmission for a smooth drive

automatic

gasoline

Winchester, VA

$55,735

2024 Jeep Grand Cherokee

Experience the 2024 Jeep Grand Cherokee, featuring all-wheel drive capability that ensures a smooth and powerful driving experience in any terrain

automatic

gasoline

Winchester, VA

$55,735

CARSBBS.COM

2025 Jeep Grand Cherokee

Experience luxury and performance with the 2025 Jeep Grand Cherokee, featuring 4WD capability, ideal for any terrain. Perfect for adventurers who seek a reliable ride

automatic

gasoline

Winchester, VA

$55,460

CARSBBS.COM

2025 Jeep Grand Cherokee

Explore this brand new 2025 Jeep Grand Cherokee equipped with 4WD and an automatic transmission, perfect for any adventure

automatic

gasoline

Winchester, VA

$55,460

CARSBBS.COM

2025 Jeep Grand Cherokee

Explore the rugged versatility of the 2025 Jeep Grand Cherokee, equipped with 4WD for all-terrain adventures and featuring an automatic transmission for effortless driving

automatic

gasoline

Winchester, VA

$54,865

2025 Jeep Grand Cherokee

Experience the future of driving with this 2025 Jeep Grand Cherokee, equipped with a 4WD system and smooth automatic transmission. Perfect for off-road adventures or daily commutes!

automatic

gasoline

Winchester, VA

$54,835

2025 Jeep Grand Cherokee

Experience the 2025 Jeep Grand Cherokee, a luxurious SUV designed for those who seek adventure combined with comfort. Enjoy powerful 4WD capabilities and an automatic transmission for a smooth ride

automatic

gasoline

Winchester, VA

$54,835

2025 Jeep Grand Cherokee

Introducing the 2025 Jeep Grand Cherokee, a robust SUV equipped with 4WD and an automatic transmission, perfect for both off-road adventures and everyday drives

automatic

gasoline

Winchester, VA

$54,835

CARSBBS.COM

2025 Jeep Grand Cherokee

Experience the ultimate in adventure and comfort with the 2025 Jeep Grand Cherokee, featuring 4WD for superior handling and an automatic transmission for an effortless driving experience

automatic

gasoline

Winchester, VA

$54,835

2025 Jeep Grand Cherokee

Discover the rugged elegance of this 2025 Jeep Grand Cherokee with luxurious features and 4WD capability, perfect for any adventure

automatic

gasoline

Winchester, VA

$52,735