Pickup Trucks for Sale inWinchester, VA

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27,129 vehicles found

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Year:
2025
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
401 hp 6.6L V8
Exterior color:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
20,977
Stock #:
MG60202S
VIN:
2GC4KME79S1122582
Sterling Gray Metallic 2025 Chevrolet Silverado 2500HD Pickup Truck Four-Wheel Drive Automatic
Fred Beans Buick GMC Mechanicsburg

Sponsored by Fred Beans Buick GMC Mechanicsburg

2025 Chevrolet Silverado 2500HD

Custom Crew Cab 4WD

20,977 mi

Mechanicsburg, PA
97 mi away
Fair Deal

$51,877

Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,300
Stock #:
A13489A
VIN:
3GCPYCEF4KG217748
Shadow Gray Metallic 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,300 mi

Grafton, WV
100 mi away
Great Deal

$21,895

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:
White
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
34,891
Stock #:
36P1382
VIN:
3TMCZ5AN7PM629501
White 2023 Toyota Tacoma Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2023 Toyota Tacoma

TRD Off Road Double Cab 4WD

34,891 mi

Charlottesville, VA
80 mi away
Fair Deal
Manufacturer certified

$40,798

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
5
Stock #:
C15980
VIN:
3GCUKFEL3TG337022
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $68,980

$57,370

Year:
2026
Make:
GMC
Model:
Sierra 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
470 hp 6.6L V8 Biodiesel
Exterior color:
Coastal Dune
Fuel type:
Biodiesel
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
5
Stock #:
48058
VIN:
1GT4ULEY8TF308041
Coastal Dune 2026 GMC Sierra 2500HD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$2,000

 

2026 GMC Sierra 2500HD

Pro Crew Cab 4WD

Huntingdon, PA
91 mi away

New car

MSRP $72,934

$62,480

$60,480

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
405 hp 6.8L V8 Flex Fuel Vehicle
Exterior color:
Oxford White
Fuel type:
Flex Fuel Vehicle
Interior color:
Med Drk Slate
Transmission:
Automatic
Mileage:
2
Stock #:
MFU60632
VIN:
1FTRF3BA3TEF59448
Oxford White 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

XL Regular Cab LB 4WD

Mechanicsburg, PA
97 mi away

New car

MSRP $70,012

$63,275

Year:
2026
Make:
GMC
Model:
Sierra 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
470 hp 6.6L V8 Biodiesel
Exterior color:
Downpour Metallic
Fuel type:
Biodiesel
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
6
Stock #:
48060
VIN:
1GT4ULEY4TF313785
Downpour Metallic 2026 GMC Sierra 2500HD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$2,000

 

2026 GMC Sierra 2500HD

Pro Crew Cab 4WD

Huntingdon, PA
91 mi away

New car

MSRP $73,759

$62,980

$60,980

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Stock #:
75489
VIN:
1GCUKDEDXTZ443903
Sterling Gray Metallic 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

LT Crew Cab 4WD

Warrenton, VA
37 mi away

New car

MSRP $59,885

$49,450

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10
Stock #:
C16089
VIN:
3GCUKEED0TG422676
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

RST Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $60,695

$47,835

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.7L V8 Biodiesel
Exterior color:
Glacier Gray Metallic TriCoat
Fuel type:
Biodiesel
Interior color:
Black Onyx
Transmission:
Automatic
Mileage:
15
Stock #:
T260647
VIN:
1FT8W3BM6TEF28815
Glacier Gray Metallic TriCoat 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

Lariat Crew Cab 4WD

Laurel, MD
70 mi away

New car

MSRP $100,780

$90,299

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
430 hp 7.3L V8
Exterior color:
Carbonized Gray Metallic
Fuel type:
Gasoline
Interior color:
Medium Dark Slate
Transmission:
Automatic
Mileage:
4
Stock #:
T36070
VIN:
1FT8X3BN1TEF38853
Carbonized Gray Metallic 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

XLT SuperCab 4WD

Front Royal, VA
14 mi away

New car

MSRP $62,030

$53,676

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
430 hp 7.3L V8
Exterior color:
Avalanche
Fuel type:
Gasoline
Interior color:
Medium Dark Slate
Transmission:
Automatic
Mileage:
8
Stock #:
T36082
VIN:
1FT8X3BN3TEF55847
Avalanche 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

XLT SuperCab 4WD

Front Royal, VA
14 mi away

New car

MSRP $62,650

$54,240

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10
Stock #:
C16121C
VIN:
3GCUKCEDXTG379145
Black 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $58,065

$46,505

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
2
Stock #:
Q260799
VIN:
1GCUKEED8TZ519804
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

RST Crew Cab 4WD

Thurmont, MD
51 mi away

New car

MSRP $62,494

$51,932

Year:
2026
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
16
Stock #:
00118525
VIN:
1C6PJTAG0TL176114
Black 2026 Jeep Gladiator Pickup Truck Four-Wheel Drive Automatic

 

2026 Jeep Gladiator

Willys '41 4dr Crew Cab 4WD

Prince Frederick, MD
96 mi away

New car

MSRP $51,535

$46,798

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
8
Stock #:
C16189
VIN:
3GCUKCED3TG522453
Sterling Gray Metallic 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $58,915

$47,355

Year:
2025
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
401 hp 6.6L V8
Exterior color:
Sterling Gray Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
20,977
Stock #:
MG60202S
VIN:
2GC4KME79S1122582
Sterling Gray Metallic 2025 Chevrolet Silverado 2500HD Pickup Truck Four-Wheel Drive Automatic
Fred Beans Buick GMC Mechanicsburg

Sponsored by Fred Beans Buick GMC Mechanicsburg

2025 Chevrolet Silverado 2500HD

Custom Crew Cab 4WD

20,977 mi

Mechanicsburg, PA
97 mi away
Fair Deal

$51,877

Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Shadow Gray Metallic
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
114,300
Stock #:
A13489A
VIN:
3GCPYCEF4KG217748
Shadow Gray Metallic 2019 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive 6-Speed Automatic Overdrive

Sponsored Listing

2019 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

114,300 mi

Grafton, WV
100 mi away
Great Deal

$21,895

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:
White
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
34,891
Stock #:
36P1382
VIN:
3TMCZ5AN7PM629501
White 2023 Toyota Tacoma Pickup Truck Four-Wheel Drive Automatic
New arrival

Sponsored Listing

2023 Toyota Tacoma

TRD Off Road Double Cab 4WD

34,891 mi

Charlottesville, VA
80 mi away
Fair Deal
Manufacturer certified

$40,798

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
5
Stock #:
C15980
VIN:
3GCUKFEL3TG337022
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $68,980

$57,370

Year:
2026
Make:
GMC
Model:
Sierra 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
470 hp 6.6L V8 Biodiesel
Exterior color:
Coastal Dune
Fuel type:
Biodiesel
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
5
Stock #:
48058
VIN:
1GT4ULEY8TF308041
Coastal Dune 2026 GMC Sierra 2500HD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$2,000

 

2026 GMC Sierra 2500HD

Pro Crew Cab 4WD

Huntingdon, PA
91 mi away

New car

MSRP $72,934

$62,480

$60,480

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
405 hp 6.8L V8 Flex Fuel Vehicle
Exterior color:
Oxford White
Fuel type:
Flex Fuel Vehicle
Interior color:
Med Drk Slate
Transmission:
Automatic
Mileage:
2
Stock #:
MFU60632
VIN:
1FTRF3BA3TEF59448
Oxford White 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

XL Regular Cab LB 4WD

Mechanicsburg, PA
97 mi away

New car

MSRP $70,012

$63,275

Year:
2026
Make:
GMC
Model:
Sierra 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
470 hp 6.6L V8 Biodiesel
Exterior color:
Downpour Metallic
Fuel type:
Biodiesel
Interior color:
Jet Black, Cloth Seat Trim
Transmission:
Automatic
Mileage:
6
Stock #:
48060
VIN:
1GT4ULEY4TF313785
Downpour Metallic 2026 GMC Sierra 2500HD Pickup Truck Four-Wheel Drive Automatic
Price drop

-$2,000

 

2026 GMC Sierra 2500HD

Pro Crew Cab 4WD

Huntingdon, PA
91 mi away

New car

MSRP $73,759

$62,980

$60,980

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Stock #:
75489
VIN:
1GCUKDEDXTZ443903
Sterling Gray Metallic 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

LT Crew Cab 4WD

Warrenton, VA
37 mi away

New car

MSRP $59,885

$49,450

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10
Stock #:
C16089
VIN:
3GCUKEED0TG422676
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

RST Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $60,695

$47,835

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.7L V8 Biodiesel
Exterior color:
Glacier Gray Metallic TriCoat
Fuel type:
Biodiesel
Interior color:
Black Onyx
Transmission:
Automatic
Mileage:
15
Stock #:
T260647
VIN:
1FT8W3BM6TEF28815
Glacier Gray Metallic TriCoat 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

Lariat Crew Cab 4WD

Laurel, MD
70 mi away

New car

MSRP $100,780

$90,299

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
430 hp 7.3L V8
Exterior color:
Carbonized Gray Metallic
Fuel type:
Gasoline
Interior color:
Medium Dark Slate
Transmission:
Automatic
Mileage:
4
Stock #:
T36070
VIN:
1FT8X3BN1TEF38853
Carbonized Gray Metallic 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

XLT SuperCab 4WD

Front Royal, VA
14 mi away

New car

MSRP $62,030

$53,676

Year:
2026
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
430 hp 7.3L V8
Exterior color:
Avalanche
Fuel type:
Gasoline
Interior color:
Medium Dark Slate
Transmission:
Automatic
Mileage:
8
Stock #:
T36082
VIN:
1FT8X3BN3TEF55847
Avalanche 2026 Ford F-350 Super Duty Pickup Truck Four-Wheel Drive Automatic

 

2026 Ford F-350 Super Duty

XLT SuperCab 4WD

Front Royal, VA
14 mi away

New car

MSRP $62,650

$54,240

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Black
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
10
Stock #:
C16121C
VIN:
3GCUKCEDXTG379145
Black 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $58,065

$46,505

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
2
Stock #:
Q260799
VIN:
1GCUKEED8TZ519804
Summit White 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

RST Crew Cab 4WD

Thurmont, MD
51 mi away

New car

MSRP $62,494

$51,932

Year:
2026
Make:
Jeep
Model:
Gladiator
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
285 hp 3.6L V6
Exterior color:
Black
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
16
Stock #:
00118525
VIN:
1C6PJTAG0TL176114
Black 2026 Jeep Gladiator Pickup Truck Four-Wheel Drive Automatic

 

2026 Jeep Gladiator

Willys '41 4dr Crew Cab 4WD

Prince Frederick, MD
96 mi away

New car

MSRP $51,535

$46,798

Year:
2026
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Sterling Gray Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
8
Stock #:
C16189
VIN:
3GCUKCED3TG522453
Sterling Gray Metallic 2026 Chevrolet Silverado 1500 Pickup Truck Four-Wheel Drive Automatic

 

2026 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

Waynesboro, PA
51 mi away

New car

MSRP $58,915

$47,355

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