CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Best Pickup Trucks For Sale in Winchester, KY

1,862 results
Winchester, KY
2022 Ford F-150 Raptor SuperCrew 4WD Mike Castrucci Ford

2022 Ford F-150

Raptor SuperCrew 4WD

70,634 miles

$52,950

Great Deal
Certified Pre-Owned
Milford, OH
83 mi away
Year:
2022
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
450 hp 3.5L V6
Exterior color:
Black Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
70,634
Stock number:
286389
VIN:
1FTFW1RG5NFA08016

Sponsored

2022 Chevrolet Colorado Work Truck Extended Cab RWD

2022 Chevrolet Colorado

Work Truck Extended Cab RWD

73,927 miles

$16,989

Good Deal
Cincinnati, OH
89 mi away
Year:
2022
Make:
Chevrolet
Model:
Colorado
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
200 hp 2.5L I4
Exterior color:
Summit White
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Dark Ash
Transmission:
6-Speed Automatic
Mileage:
73,927
Stock number:
1047795
VIN:
1GCHSBEA8N1195020

Sponsored

2023 RAM 1500 Big Horn Crew Cab 4WD

2023 RAM 1500

Big Horn Crew Cab 4WD

34,910 miles

$33,995

Good Deal
Mt Orab, OH
74 mi away
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:
Blue
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
34,910
Stock number:
13746A
VIN:
1C6SRFFTXPN580090

Sponsored

2021 Ford F-150 XLT SuperCab RWD

2021 Ford F-150

XLT SuperCab RWD

152,066 miles

$12,999

Great Deal
Ashland, KY
91 mi away
Year:
2021
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
3.3L V6 Flex Fuel Vehicle
Exterior color:
Blue
Combined gas mileage:
22 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
Automatic
Mileage:
152,066
Stock number:
D58476
VIN:
1FTEX1CB8MKD58476

2022 Ford F-150 Lariat SuperCrew 4WD

2022 Ford F-150

Lariat SuperCrew 4WD

23,965 miles

$39,500

Great Deal
Mount Orab, OH
73 mi away
Year:
2022
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
325 hp 2.7L V6
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
23,965
Stock number:
PMT-1520
VIN:
1FTEW1EP5NKD35864

2023 Chevrolet Silverado 1500 ZR2 Crew Cab 4WD

2023 Chevrolet Silverado 1500

ZR2 Crew Cab 4WD

50,539 miles

$46,446

Great Deal
Batavia, OH
76 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Gray
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
50,539
Stock number:
11351855A
VIN:
3GCUDHEL0PG328905

Preparing for a close up...

Photos coming soon

2021 Ford F-150

Lariat SuperCrew 4WD

153,620 miles

$24,000

Good Deal
Louisville, KY
91 mi away
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:
Oxford White
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Medium Dark Slate
Transmission:
Automatic
Mileage:
153,620
Stock number:
CH811
VIN:
1FTFW1E89MKF03193

Preparing for a close up...

Photos coming soon

2022 Jeep Gladiator

Willys Crew Cab 4WD

16,152 miles

$30,581

Great Deal
Madison, IN
85 mi away
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:
Firecracker Red Clearcoat
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
16,152
Stock number:
157438
VIN:
1C6HJTAG9NL157438

Preparing for a close up...

Photos coming soon

2023 Toyota Tacoma

SR5 V6 Double Cab RWD

19,910 miles

$31,602

Great Deal
Ashland, KY
91 mi away
Year:
2023
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
278 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Cement
Transmission:
6-Speed Automatic
Mileage:
19,910
Stock number:
KNU756
VIN:
3TMAZ5CN4PM198510

Preparing for a close up...

Photos coming soon

2023 Toyota Tacoma

Trail Edition Double Cab 4WD

32,308 miles

$37,316

Good Deal
Cincinnati, OH
83 mi away
Year:
2023
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
278 hp 3.5L V6
Exterior color:
Black
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
32,308
Stock number:
6316843A
VIN:
3TMCZ5AN0PM587754

Preparing for a close up...

Photos coming soon

2023 Ford Maverick

XLT SuperCrew FWD

44,782 miles

$24,128

Good Deal
Certified Pre-Owned
Cincinnati, OH
90 mi away
Year:
2023
Make:
Ford
Model:
Maverick
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
2.5L I4 Hybrid
Exterior color:
Carbonized Gray Metallic
Combined gas mileage:
37 MPG
Fuel type:
Hybrid
Interior color:
Blue (Navy Pier / Medium Slate)
Transmission:
Continuously Variable Transmission
Mileage:
44,782
Stock number:
T251240A
VIN:
3FTTW8E37PRA19264

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

83,706 miles

$34,990

Fair Deal
Ashland, KY
91 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
83,706
Stock number:
T057443A
VIN:
3GCPYFELXMG221961

Preparing for a close up...

Photos coming soon

2021 Chevrolet Silverado 1500

LT Crew Cab RWD

76,375 miles

$26,998

Good Deal
Huntington, WV
97 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
76,375
Stock number:
T46020AAAA
VIN:
3GCPWCED4MG370458

Preparing for a close up...

Photos coming soon

2023 GMC Sierra 1500

Denali Crew Cab 4WD

38,954 miles

$49,926

Good Deal
Batavia, OH
76 mi away
Year:
2023
Make:
GMC
Model:
Sierra 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
38,954
Stock number:
11T11078
VIN:
1GTUUGEL3PZ274882

Preparing for a close up...

Photos coming soon

2022 Toyota Tacoma

SR V6 Double Cab 4WD

43,215 miles

$30,035

Good Deal
Dry Ridge, KY
53 mi away
Year:
2022
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
278 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
43,215
Stock number:
1267
VIN:
3TYCZ5AN8NT082191

Preparing for a close up...

Photos coming soon

2022 Chevrolet Colorado

LT Crew Cab 4WD

48,685 miles

$26,909

Good Deal
Batavia, OH
76 mi away
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:
Blue
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
48,685
Stock number:
11351875A
VIN:
1GCGTCEN0N1304281

Preparing for a close up...

Photos coming soon

2022 Ford F-150

Lariat SuperCrew 4WD

78,832 miles

$34,349

Great Deal
Mount Sterling, KY
13 mi away
Year:
2022
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 3.5L V6 Hybrid
Exterior color:
Smoked Quartz Metallic Tinted Clearcoat
Combined gas mileage:
23 MPG
Fuel type:
Hybrid
Interior color:
Brown (Baja Tan)
Transmission:
Automatic
Mileage:
78,832
Stock number:
QA64907
VIN:
1FTFW1ED7NFA64907

Preparing for a close up...

Photos coming soon

2023 Toyota Tacoma

SR V6 Double Cab 4WD

25,784 miles

$32,705

Great Deal
Dry Ridge, KY
53 mi away
Year:
2023
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
278 hp 3.5L V6
Exterior color:
Black
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
25,784
Stock number:
1332
VIN:
3TMCZ5AN5PM537951

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Crew Cab 4WD

24,066 miles

$32,719

Good Deal
Ivel, KY
88 mi away
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:
Ash
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
24,066
Stock number:
H3847
VIN:
1GCPDBEK5PZ114171

Preparing for a close up...

Photos coming soon

2022 RAM 1500

Big Horn Quad Cab 4WD

44,146 miles

$26,699

Good Deal
Greendale, IN
86 mi away
Year:
2022
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
305 hp 3.6L V6
Exterior color:
Bright White Clearcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Diesel Gray/Black
Transmission:
8-Speed Automatic
Mileage:
44,146
Stock number:
C6147JR
VIN:
1C6RRFBG0NN435208

Preparing for a close up...

Photos coming soon

2023 RAM 1500

Big Horn Quad Cab 4WD

43,929 miles

$28,151

Good Deal
Ivel, KY
88 mi away
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:
Billet Silver Metallic Clearcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
43,929
Stock number:
H3971
VIN:
1C6RRFBG1PN571138

Preparing for a close up...

Photos coming soon

2023 Ford F-150

XLT SuperCrew 4WD

26,361 miles

$38,990

Good Deal
Pikeville, KY
93 mi away
Year:
2023
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
26,361
Stock number:
MST190A
VIN:
1FTFW1E81PFC06531

Preparing for a close up...

Photos coming soon

2021 Ford F-150

XL SuperCrew LB 4WD

146,465 miles

$21,995

Good Deal
Louisville, KY
81 mi away
Year:
2021
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 5L V8 Flex Fuel Vehicle
Exterior color:
Black
Combined gas mileage:
19 MPG
Fuel type:
Flex Fuel Vehicle
Transmission:
Automatic
Mileage:
146,465
Stock number:
12229
VIN:
1FTFW1E55MKD12229

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

Custom Crew Cab 4WD

28,516 miles

$34,543

Fair Deal
Ivel, KY
88 mi away
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:
28,516
Stock number:
H3998
VIN:
1GCPDBEKXPZ327360

Sponsored

  • Best Pickup Trucks For Sale in Lexington KY

  • Best Pickup Trucks For Sale in London KY

  • Best Pickup Trucks For Sale in Cincinnati OH

  • Best Pickup Trucks For Sale in Louisville KY

  • Best Pickup Trucks For Sale in Huntington WV

  • Best Pickup Trucks For Sale in Dayton OH

  • Best Pickup Trucks For Sale in Columbus IN

  • Best Pickup Trucks For Sale in Morristown TN

  • Best Pickup Trucks For Sale in Knoxville TN

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Dan Cummins Chevrolet Buick

  • Dan Cummins Georgetown

  • Dan Cummins Chrysler Dodge Jeep Ram

  • Freedom Chrysler Dodge Jeep RAM of Lexington

  • Dan Cummins Ford Lincoln

  • McFarland Chevrolet Buick

  • Adam's Auto Sales

  • Tim Short Chrysler Dodge Jeep RAM of Morehead

  • Don Franklin Auto Mall Lexington

  • Drive In Motors

  • Paradise Motorsports I

  • Dutch's Chevrolet

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.