Best Pickup Trucks For Sale inWinchester, KY
1,872 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2021
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Red
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 61,501
- Stock #:
- 42MG269787T1
- VIN:
- 3GTU9BET6MG269787
New arrival
Sponsored by Jeff Wyler Fairfield Kia
2021 GMC Sierra 1500
SLE Crew Cab 4WD
61,501 mi
Fairfield, OH
94 mi away
Fair Deal
$32,551
- Year:
- 2023
- Make:
- Honda
- Model:
- Ridgeline
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 280 hp 3.5L V6
- Exterior color:
- Crystal Black Pearl
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 9-Speed Automatic Overdrive
- Mileage:
- 31,267
- Stock #:
- PB015941
- VIN:
- 5FPYK3F57PB015941
Price drop
-$1,039
Sponsored Listing
2023 Honda Ridgeline
RTL AWD
31,267 mi
Cincinnati, OH
91 mi away
Great Deal
$30,760
$29,721
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 308 hp 3.6L V6
- Exterior color:
- SAND DUNE METALLIC
- Fuel type:
- Gasoline
- Mileage:
- 70,067
- Stock #:
- 26619A
- VIN:
- 1GCGTEEN2N1245505
New arrival
Sponsored Listing
2022 Chevrolet Colorado
ZR2 Crew Cab 4WD
70,067 mi
La Grange, KY
71 mi away
Fair Deal
$32,572
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 260 hp 3L V6 Diesel
- Exterior color:
- Hydro Blue Pearlcoat
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,039
- Stock #:
- G1260A
- VIN:
- 1C6JJTAM3ML594969
Price drop
-$1,215
2021 Jeep Gladiator
Willys Crew Cab 4WD
50,039 mi
Grayson, KY
72 mi away
Great Deal
$31,699
$30,484
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Sting-Gray Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 71,591
- Stock #:
- 549402
- VIN:
- 1C6HJTAG0ML549402
2021 Jeep Gladiator
Willys Crew Cab 4WD
71,591 mi
Richmond, KY
16 mi away
Good Deal
$26,700
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Diamond Black Crystal Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 39,455
- Stock #:
- P0187
- VIN:
- 1C6SRFFT9PN685204
New arrival
2023 RAM 1500
Big Horn Crew Cab 4WD
39,455 mi
Middlesboro, KY
97 mi away
Good Deal
$36,858
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 80,912
- Stock #:
- T260163A
- VIN:
- 1C6HJTAG3ML513431
2021 Jeep Gladiator
Sport Crew Cab 4WD
80,912 mi
Cincinnati, OH
90 mi away
Fair Deal
$25,109
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 32,874
- Stock #:
- H4157
- VIN:
- 1C6RRFFG6PN578032
2023 RAM 1500
Big Horn Crew Cab 4WD
32,874 mi
Ivel, KY
88 mi away
Great Deal
$32,857
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Radiant Red Tintcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 46,839
- Stock #:
- 44500A
- VIN:
- 1GCUDGED4PZ312600
Price drop
-$1,054
2023 Chevrolet Silverado 1500
LTZ Crew Cab 4WD
46,839 mi
Alexandria, KY
70 mi away
Great Deal
$40,221
$39,167
- Year:
- 2021
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,926
- Stock #:
- MFC52936
- VIN:
- 1FTFW1E8XMFC52936
Price drop
-$2,044
2021 Ford F-150
XLT SuperCrew 4WD
52,926 mi
West Harrison, IN
95 mi away
Great Deal
$32,037
$29,993
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 14,571
- Stock #:
- Z2411
- VIN:
- 1C6SRFFT4PN634600
2023 RAM 1500
Big Horn Crew Cab 4WD
14,571 mi
Florence, KY
75 mi away
Fair Deal
$39,766
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Diamond Black Crystal Pearlcoat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 23,969
- Stock #:
- H4280
- VIN:
- 1C6RRFBG7PN555008
New arrival
2023 RAM 1500
Big Horn Quad Cab 4WD
23,969 mi
Ivel, KY
88 mi away
Great Deal
$32,256
- Year:
- 2023
- Make:
- Nissan
- Model:
- Frontier
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- 4X2
- Engine:
- 310 hp 3.8L V6
- Exterior color:
- Tactical Green Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Steel)
- Transmission:
- 9-Speed Automatic
- Mileage:
- 13,984
- Stock #:
- 15034
- VIN:
- 1N6ED1EJ6PN615034
2023 Nissan Frontier
PRO-X Crew Cab RWD
13,984 mi
Richmond, KY
16 mi away
Good Deal
$31,400
- Year:
- 2022
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 325 hp 2.7L V6
- Exterior color:
- Gray Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- Automatic
- Mileage:
- 32,102
- Stock #:
- F1379A
- VIN:
- 1FTEX1EP2NKF29040
Price drop
-$1,810
2022 Ford F-150
XLT SuperCab 4WD
32,102 mi
Grayson, KY
72 mi away
Good Deal
$34,906
$33,096
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 325 hp 2.7L V6
- Exterior color:
- Atlas Blue Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 22,338
- Stock #:
- PX3286
- VIN:
- 1FTEW1EP2PKF54588
Price drop
-$2,244
2023 Ford F-150
Lariat SuperCrew 4WD
22,338 mi
Grayson, KY
72 mi away
Great Deal
$45,699
$43,455
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 2 doors
- Drivetrain:
- 4X2
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- White
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 98,522
- Stock #:
- 526029
- VIN:
- 1GCPAAEK2NZ526029
New arrival
2022 Chevrolet Silverado 1500
Work Truck Crew Cab RWD
98,522 mi
Cincinnati, OH
81 mi away
Good Deal
$19,988
- Year:
- 2022
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Bright White Clearcoat
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 39,575
- Stock #:
- 430570
- VIN:
- 1C6RRFMG7NN430570
2022 RAM 1500
Big Horn Crew Cab 4WD
39,575 mi
Richmond, KY
17 mi away
Fair Deal
$34,023
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,608
- Stock #:
- 1714
- VIN:
- 1GCRDKEK4PZ287348
2023 Chevrolet Silverado 1500
LT Double Cab 4WD
50,608 mi
Dry Ridge, KY
53 mi away
Good Deal
$30,458
- Year:
- 2021
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 73,970
- Stock #:
- 551332
- VIN:
- 1C6RR7KG3MS551332
2021 RAM 1500
Classic Tradesman Crew Cab 4WD
73,970 mi
Richmond, KY
18 mi away
Good Deal
$22,233
- Year:
- 2023
- Make:
- Nissan
- Model:
- Frontier
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 3.8L V6
- Exterior color:
- Baja Storm
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black (Charcoal)
- Transmission:
- 9-Speed Automatic
- Mileage:
- 14,068
- Stock #:
- PN668952
- VIN:
- 1N6ED1EK0PN668952
2023 Nissan Frontier
PRO-4X Crew Cab 4WD
14,068 mi
Cincinnati, OH
90 mi away
Good Deal
$34,948
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 308 hp 3.6L V6
- Exterior color:
- Cherry Red Tintcoat
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 93,040
- Stock #:
- ST107828
- VIN:
- 1GCGTEEN5N1107828
2022 Chevrolet Colorado
ZR2 Crew Cab 4WD
93,040 mi
Cincinnati, OH
83 mi away
Good Deal
$26,898
- Year:
- 2022
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Hydro Blue Pearlcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 54,568
- Stock #:
- NL176905
- VIN:
- 1C6HJTAGXNL176905
2022 Jeep Gladiator
Sport Crew Cab 4WD
54,568 mi
Cincinnati, OH
75 mi away
Fair Deal
$27,248
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Silver Ice Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,176
- Stock #:
- P8991A
- VIN:
- 3GCPDCED7NG624218
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,176 mi
Cincinnati, OH
91 mi away
Great Deal
$33,346
- Year:
- 2022
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Silver Zynith Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,049
- Stock #:
- R0801
- VIN:
- 1C6HJTAG9NL131180
Sponsored Listing
2022 Jeep Gladiator
Willys Crew Cab 4WD
51,049 mi
Hazard, KY
72 mi away
Good Deal
$28,837
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