Used Cars in Winchester, KY For Sale Under $50,000 (296 results)

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State:Kentucky

City:Winchester, KY

Year

2025
(27)
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(6)
2023
(12)
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(17)
2021
(43)
2020
(51)
2019
(27)
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(23)
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(22)
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(28)
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(10)
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(11)
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(5)
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(2)
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(3)
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(3)
2009
(1)
2008
(1)
2005
(1)
1972
(1)
1967
(2)

Zip

Price

Mileage

0 - 50000
(234)
50000 - 100000
(54)
100000 - 150000
(6)
150000 - 200000
(1)
200000 - 1000000
(1)

Make

Jeep
(70)
Chevrolet
(36)
Ford
(36)
RAM
(29)
Nissan
(27)
Dodge
(24)
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(16)
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(14)
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(10)
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(8)
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(3)
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(2)
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(1)
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(1)
De Tomaso
(1)
Genesis
(1)
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(1)
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(1)
Mitsubishi
(1)
Pontiac
(1)

Transmission type

automatic
(225)
manual
(6)

Color

Black
(30)
White
(22)
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(11)
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(10)
Gray
(5)
Red
(3)

Body

Suv
(7)
Sedan
(5)
Truck
(3)
Convertible
(2)
Coupe
(2)
Crew cab
(2)
Pickup truck
(2)
Hatchback
(1)

Drive

fwd
(55)
4wd
(46)
awd
(36)
rwd
(16)

Fuel

gasoline
(200)
diesel
(5)
flex fuel
(1)
hybrid
(1)

Category

classic cars
(3)
conversion van
(1)

State

Kentucky

City

Winchester, KY

Features

Air conditioning
(117)
AM/FM radio
(114)
Cruise control
(113)
Power windows
(107)
Backup camera
(103)
Bluetooth
(94)
Bucket seats
(92)
MP3 player
(87)
Power locks
(77)
Aluminum wheels
(59)
CD player
(48)
Alloy wheels
(40)
ABS brakes
(26)
Tachometer
(23)
Climate control
(21)
Automatic temperature control
(17)
Electronic stability control
(17)
Four wheel independent suspension
(17)
Front dual zone A/C
(17)
Power steering
(17)
Remote start
(13)
Brake assist
(12)
Power driver seat
(12)
Power seats
(11)
Sunroof/Moonroof
(11)
Automatic headlights
(10)
Keyless entry
(10)
Leather seats
(10)
Adjustable steering wheel
(9)
Child-safety locks
(9)

2021 RAM 3500

Explore the rugged capabilities of this 2021 Ram 3500, equipped with a robust 4WD system and an automatic transmission, perfect for any terrain

automatic

diesel

Winchester, KY

$49,988

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

2024 RAM 1500

This 2024 Ram 1500 is equipped with 4WD and features an automatic transmission, offering a robust and reliable driving experience

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

2022 RAM 2500

This powerful 2022 Ram 2500 features a reliable automatic transmission and robust 4WD capability, making it the perfect companion for both work and play

automatic

diesel

Winchester, KY

$46,988

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

2024 Dodge Hornet

Discover the innovative 2024 Dodge Hornet, featuring all-wheel drive and a smooth automatic transmission for effortless performance

automatic

plug-in hybrid

Winchester, KY

$46,085

2022 RAM 2500

This rugged 2022 Ram 2500 is equipped with an automatic transmission and robust 4WD, perfect for tackling tough terrains, all at an attractive price of $44,988

automatic

diesel

Winchester, KY

$44,988

2022 ram 2500 big horn crew cab 4x4 8' box

Explore the 2022 RAM 2500 Big Horn Crew Cab in Bright White Clearcoat. With just over 59,000 miles, this powerful diesel truck offers four-wheel drive and comes with a clean, one-owner CARFAX

59,202 mi.

White

Crew cab

automatic

diesel

Winchester, KY

$44,988

2021 RAM 1500

This 2021 Ram 1500 offers a powerful driving experience with its 4WD capabilities and smooth automatic transmission, perfect for any terrain or adventure

automatic

gasoline

Winchester, KY

$44,988

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