Used Jeep Cars in Winchester, KY For Sale Under $40,000 (56 results)

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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

2025 Jeep Compass

Experience the 2025 Jeep Compass, a powerful 4WD SUV designed for adventure with an automatic transmission. Perfect for navigating any terrain with confidence!

automatic

gasoline

Winchester, KY

$37,115

2021 Jeep Wrangler

Discover the rugged charm of this 2021 Jeep Wrangler, equipped with 4WD and an automatic transmission, perfect for off-road adventures and everyday driving in Winchester, KY

automatic

plug-in hybrid

Winchester, KY

$36,988

2021 jeep wrangler unlimited sahara

This 2021 Jeep Wrangler Unlimited Sahara in Granite Crystal Metallic Clearcoat boasts low mileage and a rugged four-wheel drive system. It includes a CarFax report and a powertrain guarantee, ensuring you drive with confidence

18,593 mi.

Granite crystal metallic clearcoat

automatic

gasoline

Winchester, KY

$35,988

2025 Jeep Compass

Discover the newly released 2025 Jeep Compass, equipped with a robust 4WD system and an automatic transmission. A perfect blend of style, comfort, and performance on and off the road!

automatic

gasoline

Winchester, KY

$35,135

2023 jeep wrangler sport

This 2023 Jeep Wrangler Sport comes with a sleek Black Clearcoat exterior and a stylish black interior. With low mileage of 33,706 miles, it's a perfect blend of adventure and comfort, ready for your next journey

33,706 mi.

Black

automatic

gasoline

Winchester, KY

$34,988

2021 Jeep Wrangler

This 2021 Jeep Wrangler features a robust 4WD system and comes equipped with an automatic transmission, perfect for off-road adventures or city drives

automatic

plug-in hybrid

Winchester, KY

$34,988

2021 jeep wrangler unlimited sahara

This 2021 Jeep Wrangler Unlimited Sahara, with a striking Granite Crystal Metallic exterior, boasts 45,030 miles and offers four-wheel drive and a powerful 2.0L engine. It's perfect for all your adventures!

45,030 mi.

Granite crystal metallic clearcoat

automatic

gasoline

Winchester, KY

$34,988

2021 Jeep Wrangler

This 2021 Jeep Wrangler with 4WD is ready for your next adventure. With an automatic transmission, it's perfect for both off-road and urban driving!

automatic

plug-in hybrid

Winchester, KY

$33,988

2025 Jeep Compass

Discover the 2025 Jeep Compass, a versatile 4WD SUV designed for adventure and comfort. Experience dynamic driving with its automatic transmission, perfect for any journey

automatic

gasoline

Winchester, KY

$33,380

2025 Jeep Compass

Explore the outdoors with the 2025 Jeep Compass, featuring a powerful 4WD system and smooth automatic transmission for an exhilarating driving experience

automatic

gasoline

Winchester, KY

$33,380

2025 Jeep Compass

Experience the versatility and comfort of the 2025 Jeep Compass, equipped with 4WD for all-terrain adventures and an automatic transmission for a smooth, effortless drive

automatic

gasoline

Winchester, KY

$33,035

2025 Jeep Compass

Explore the great outdoors in this brand-new 2025 Jeep Compass, featuring an automatic transmission and a versatile 4WD drive. Perfect for both city streets and rugged terrains

automatic

gasoline

Winchester, KY

$33,035

2025 Jeep Compass

Discover the new 2025 Jeep Compass, a perfect blend of style and power with its robust 4WD capabilities and smooth automatic transmission, ready to tackle any terrain

automatic

gasoline

Winchester, KY

$33,035

2025 Jeep Compass

Check out this brand-new 2025 Jeep Compass! Equipped with 4WD and an automatic transmission, it's ready for any adventure. Priced at $33,035, it's the perfect blend of style and capability

automatic

gasoline

Winchester, KY

$33,035

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