Used Pickup Trucks for Sale nearWinchester, VA
10,767 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 2500HD
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 401 hp 6.6L V8
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 118,022
- Stock #:
- M257395
- VIN:
- 1GC1YLE76MF257395
Sponsored by True Gear Motors
2021 Chevrolet Silverado 2500HD
Work Truck Crew Cab 4WD
118,022 mi
Falls Church, VA
57 mi away
Good Deal
$27,890
- Year:
- 2025
- Make:
- Ford
- Model:
- Maverick
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 238 hp 2L I4
- Exterior color:
- Oxford White
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black Onyx
- Transmission:
- 7-Speed Automatic
- Mileage:
- 37,730
- Stock #:
- 23368A
- VIN:
- 3FTCW8PAXSRA80595
Sponsored Listing
2025 Ford Maverick
Lobo SuperCrew AWD
37,730 mi
Madison, VA
57 mi away
Fair Deal
$34,724
- Year:
- 2021
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Billet Silver Metallic Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 74,605
- Stock #:
- 805059
- VIN:
- 1C6SRFJTXMN805059
Sponsored Listing
2021 RAM 1500
Laramie Crew Cab 4WD
74,605 mi
Ebensburg, PA
95 mi away
Fair Deal
$33,968
- Year:
- 2021
- Make:
- RAM
- Model:
- 2500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 410 hp 6.4L V8
- Exterior color:
- Delmonico Red Pearlcoat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 120,340
- Stock #:
- TG365016A
- VIN:
- 3C6UR5SJ0MG579381
New arrival
2021 RAM 2500
Limited Crew Cab 4WD
120,340 mi
Shippensburg, PA
70 mi away
Good Deal
$39,673
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Black
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 23,927
- Stock #:
- B34838
- VIN:
- 1GCUDEE8XRZ176614
Price drop
-$2,452
2024 Chevrolet Silverado 1500
RST Crew Cab 4WD
23,927 mi
Waynesboro, PA
52 mi away
Good Deal
$45,728
$43,276
- Year:
- 2020
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5L V8 Flex Fuel Vehicle
- Exterior color:
- Star White Metallic Tri-Coat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 37,889
- Stock #:
- UAA69261
- VIN:
- 1FTEW1E58LFA69261
New arrival
2020 Ford F-150
Platinum SuperCrew 4WD
37,889 mi
Windber, PA
82 mi away
Great Deal
$40,486
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 2500HD
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 470 hp 6.6L V8 Biodiesel
- Exterior color:
- Black
- Fuel type:
- Biodiesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 9,747
- Stock #:
- UF173298
- VIN:
- 1GC1YREY0RF173298
2024 Chevrolet Silverado 2500HD
High Country Crew Cab 4WD
9,747 mi
Oakland, MD
68 mi away
Great Deal
$64,790
- Year:
- 2022
- Make:
- Hyundai
- Model:
- Santa Cruz
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 191 hp 2.5L I4
- Exterior color:
- Blue Stone
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,771
- Stock #:
- V199166A
- VIN:
- 5NTJBDAE4NH024846
2022 Hyundai Santa Cruz
SEL Crew Cab AWD
43,771 mi
Glen Burnie, MD
83 mi away
Great Deal
$21,477
- Year:
- 2020
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Patriot Blue Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 81,878
- Stock #:
- U-06168
- VIN:
- 1C6SRFJT4LN193889
2020 RAM 1500
Laramie Crew Cab 4WD
81,878 mi
Harrisonburg, VA
64 mi away
Great Deal
$28,244
- Year:
- 2017
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 325 hp 2.7L V6
- Exterior color:
- Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 78,215
- Stock #:
- E32500
- VIN:
- 1FTEX1EP1HKE32500
2017 Ford F-150
XL SuperCab 4WD
78,215 mi
Duncansville, PA
89 mi away
Good Deal
$20,190
- Year:
- 2026
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3,254
- Stock #:
- XL1442
- VIN:
- 1GCPTEEK6T1117237
2026 Chevrolet Colorado
Trail Boss Crew Cab 4WD
3,254 mi
Thurmont, MD
51 mi away
Great Deal
$37,967
- Year:
- 2021
- Make:
- RAM
- Model:
- 3500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 410 hp 6.4L V8
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 89,033
- Stock #:
- PC2878
- VIN:
- 3C63R3RJ5MG529369
2021 RAM 3500
Limited Crew Cab LB 4WD
89,033 mi
Staunton, VA
87 mi away
Fair Deal
$49,719
- 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:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black (Obsidian Rush)
- Transmission:
- Automatic
- Mileage:
- 7,591
- Stock #:
- 26GT443A
- VIN:
- 3GTUUFEL7PG207809
New arrival
2023 GMC Sierra 1500
AT4X Crew Cab 4WD
7,591 mi
Altoona, PA
91 mi away
Good Deal
$59,487
Popular Pickup Truck reviews
4.5 Overall rating(10221 reviews)
Jun 6, 2026
2012 Chevrolet LT Crew Cab 4WD
Before purchasing a used Silverado 2500HD, I would strongly recommend checking the overall condition of the truck with special attention to rust, the transmission, suspension, and maintenance history. Look closely at the rocker panels, cab corners, wheel wells, frame rails, brake lines, and fuel lines for excessive rust, flaking metal, or holes. During the test drive, make sure the transmission shifts smoothly without slipping, shuddering, hard shifts, or delayed engagement into drive or reverse, and ask whether it is the original transmission or if it has ever been rebuilt or replaced. Check the engine for oil leaks, coolant leaks, unusual noises, excessive exhaust smoke, or warning lights, and ask if major components such as the water pump, radiator, or thermostat have been replaced. Pay close attention to the steering and suspension by listening for clunks, checking for loose steering, and looking for uneven tire wear that could indicate worn ball joints, tie rods, wheel bearings, or other front-end components. Also inspect the brakes for pulsation, soft pedal feel, or rusted lines, and examine the tires for uneven wear, dry rot, or signs that an alignment or suspension issue may be present. Most importantly, ask for maintenance records and receipts for major repairs, as a well-documented truck is generally a much safer purchase than one with an unknown service history. For a high-mileage Silverado 2500HD, rust, transmission condition, front-end wear, four-wheel-drive operation, and cooling system maintenance are the areas most likely to lead to expensive repairs if they have been neglected.
Apr 23, 2026
2020 Ford XLT Crew Cab 4WD
Great condition really nice interior, really good priced drives and runs great
Jan 23, 2026
2022 Hyundai SEL Premium Crew Cab AWD
The car comes with incredible features I wasn’t even prepared for. Everything is thoughtfully crafted and they make use of every inch of space with hidden storage compartments. I love it so far
Dec 6, 2025
2019 Ford XLT SuperCrew RWD
Great vehicle! Has everything I need in a strong durable truck! Will definitely buy Ford again.
Oct 17, 2025
2022 GMC Denali Ultimate Crew Cab 4WD
Love this truck! Love the inline 6 diesel! And my fiance loves the massaging seats!
- Year:
- 2022
- Make:
- GMC
- Model:
- Sierra 1500 Limited
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Onyx Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,556
- Stock #:
- PV12270
- VIN:
- 1GTR9CEK3NZ227615
2022 GMC Sierra 1500 Limited
Elevation Double Cab 4WD
59,556 mi
Rockville, MD
56 mi away
Good Deal
$29,800
- Year:
- 2018
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Brilliant Black Crystal Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 75,124
- Stock #:
- S5364A
- VIN:
- 1C6RR7MT7JS209565
2018 RAM 1500
Night Crew Cab 4WD
75,124 mi
Somerset, PA
78 mi away
Fair Deal
$28,478
- Year:
- 2024
- 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:
- 43,276
- Stock #:
- MF604951
- VIN:
- 1C6HJTAG4RL111926
2024 Jeep Gladiator
Willys Crew Cab 4WD
43,276 mi
Mechanicsburg, PA
97 mi away
Good Deal
$33,282
- Year:
- 2020
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,637
- Stock #:
- 3082342B
- VIN:
- 1C6JJTBG1LL136600
2020 Jeep Gladiator
Rubicon Crew Cab 4WD
62,637 mi
Glen Burnie, MD
83 mi away
Great Deal
$28,799
- 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:
- White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 112,665
- Stock #:
- 1097A
- VIN:
- 1C6HJTAG9ML508315
2021 Jeep Gladiator
Sport S Crew Cab 4WD
112,665 mi
Kearneysville, WV
14 mi away
Good Deal
$23,294
- 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:
- 20,562
- Stock #:
- GT6543
- VIN:
- 1GCRDDEK3PZ258645
2023 Chevrolet Silverado 1500
LT Double Cab 4WD
20,562 mi
Altoona, PA
91 mi away
Great Deal
$33,287
- Year:
- 2023
- Make:
- Ford
- Model:
- Maverick
- Body type:
- Pickup Truck
- Engine:
- 250 hp 2L I4
- Exterior color:
- Silver
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Continuously Variable Transmission
- Mileage:
- 12,689
- Stock #:
- 0FB35228
- VIN:
- 3FTTW8E95PRA38321
Price drop
-$1,000
2023 Ford Maverick
12,689 mi
Waldorf, MD
78 mi away
Great Deal
$26,799
$25,799
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 3500HD
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 401 hp 6.6L V8
- Exterior color:
- Summit White
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 17,064
- Stock #:
- 29095
- VIN:
- 1GC4YSE77LF168392
New arrival
2020 Chevrolet Silverado 3500HD
Work Truck Crew Cab 4WD
17,064 mi
Harrisonburg, VA
63 mi away
Fair Deal
$41,998
- Year:
- 2016
- Make:
- GMC
- Model:
- Canyon
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Cyber Gray Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black/Dark Ash
- Transmission:
- 6-Speed Automatic
- Mileage:
- 61,359
- Stock #:
- 19654A
- VIN:
- 1GTH6CE32G1217043
New arrival
2016 GMC Canyon
SLE Ext. Cab LB 4WD
61,359 mi
Harrisonburg, VA
63 mi away
Fair Deal
$22,358
- Year:
- 2022
- Make:
- RAM
- Model:
- 3500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 370 hp 6.7L I6 Diesel
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 69,256
- Stock #:
- R26258B
- VIN:
- 3C63R3EL4NG440689
Sponsored Listing
2022 RAM 3500
Laramie Crew Cab 4WD
69,256 mi
Front Royal, VA
17 mi away
Fair Deal
$54,615
4.5 Overall rating for Pickup Truck
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Britt O
Reviewed a 2012 Chevrolet LT Crew Cab 4WD on Jun 6, 2026
Before purchasing a used Silverado 2500HD, I would strongly recommend checking the overall condition of the truck with special attention to rust, the transmission, suspension, and maintenance history. Look closely at the rocker panels, cab corners, wheel wells, frame rails, brake lines, and fuel lines for excessive rust, flaking metal, or holes. During the test drive, make sure the transmission shifts smoothly without slipping, shuddering, hard shifts, or delayed engagement into drive or reverse, and ask whether it is the original transmission or if it has ever been rebuilt or replaced. Check the engine for oil leaks, coolant leaks, unusual noises, excessive exhaust smoke, or warning lights, and ask if major components such as the water pump, radiator, or thermostat have been replaced. Pay close attention to the steering and suspension by listening for clunks, checking for loose steering, and looking for uneven tire wear that could indicate worn ball joints, tie rods, wheel bearings, or other front-end components. Also inspect the brakes for pulsation, soft pedal feel, or rusted lines, and examine the tires for uneven wear, dry rot, or signs that an alignment or suspension issue may be present. Most importantly, ask for maintenance records and receipts for major repairs, as a well-documented truck is generally a much safer purchase than one with an unknown service history. For a high-mileage Silverado 2500HD, rust, transmission condition, front-end wear, four-wheel-drive operation, and cooling system maintenance are the areas most likely to lead to expensive repairs if they have been neglected.
Is this review helpful?
Josiah L
Reviewed a 2020 Ford XLT Crew Cab 4WD on Apr 23, 2026
Great condition really nice interior, really good priced drives and runs great
Is this review helpful?
Jesse S
Reviewed a 2022 Hyundai SEL Premium Crew Cab AWD on Jan 23, 2026
The car comes with incredible features I wasn’t even prepared for. Everything is thoughtfully crafted and they make use of every inch of space with hidden storage compartments. I love it so far
Is this review helpful?
Dale W
Reviewed a 2019 Ford XLT SuperCrew RWD on Dec 6, 2025
Great vehicle! Has everything I need in a strong durable truck! Will definitely buy Ford again.
Is this review helpful?
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