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

Diesel Trucks for Sale in Winchester, VA

3,473 results
Winchester, VA
2024 Chevrolet Silverado 3500HD High Country Crew Cab 4WD Buchanan Automotive Inc

2024 Chevrolet Silverado 3500HD

High Country Crew Cab 4WD

23,181 miles

$72,991

Fair Deal
Certified Pre-Owned
Waynesboro, PA
51 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 3500HD
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:
23,181
Stock number:
U17204
VIN:
2GC4YVEY2R1183571

Sponsored

2021 GMC Sierra 1500 SLT Crew Cab 4WD

2021 GMC Sierra 1500

SLT Crew Cab 4WD

76,623 miles

$35,777

Fair Deal
Rockville, MD
58 mi away
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:
Gray (Satin Steel Metallic)
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
76,623
Stock number:
G354271A
VIN:
3GTU9DET7MG291860

Sponsored

2023 GMC Sierra 1500 AT4 Crew Cab 4WD

2023 GMC Sierra 1500

AT4 Crew Cab 4WD

42,322 miles

$47,400

Good Deal
Prince Frederick, MD
94 mi away
Year:
2023
Make:
GMC
Model:
Sierra 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
3L I6 Diesel
Exterior color:
Summit White
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Atmosphere/Brownstone
Transmission:
Automatic
Mileage:
42,322
Stock number:
PG180285
VIN:
3GTUUEE88PG180285

Sponsored

2014 GMC Sierra 2500HD Work Truck Crew Cab SB 4WD

2014 GMC Sierra 2500HD

Work Truck Crew Cab SB 4WD

148,764 miles

$20,188

Fair Deal
Windber, PA
80 mi away
Year:
2014
Make:
GMC
Model:
Sierra 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
397 hp 6.6L V8 Diesel
Exterior color:
Summit White
Fuel type:
Diesel
Interior color:
Gray (Dark Titanium)
Transmission:
6-Speed Automatic
Mileage:
148,764
Stock number:
5781B
VIN:
1GT12ZC82EF158185

2021 Jeep Gladiator Rubicon Crew Cab 4WD

2021 Jeep Gladiator

Rubicon Crew Cab 4WD

140,688 miles

$22,500

Great Deal
Warrenton, VA
37 mi away
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:
Bright White Clearcoat
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
140,688
Stock number:
W260004A
VIN:
1C6JJTBM4ML588001

2025 RAM 2500 Laramie Crew Cab 4WD

2025 RAM 2500

Laramie Crew Cab 4WD

12,399 miles

$60,000

Good Deal
Woodbridge, VA
61 mi away
Year:
2025
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.7L I6 Diesel
Exterior color:
Bright White Clearcoat
Fuel type:
Diesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
12,399
Stock number:
A514605
VIN:
3C6UR5FL0SG514605

Preparing for a close up...

Photos coming soon

2014 Ford F-350 Super Duty

XLT Crew Cab 4WD

174,095 miles

$19,919

Good Deal
Manchester, PA
98 mi away
Year:
2014
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 6.7L V8 Biodiesel
Exterior color:
Ingot Silver Metallic - UX
Fuel type:
Biodiesel
Interior color:
Gray (Steel - 3S)
Transmission:
Automatic
Mileage:
174,095
Stock number:
A24777
VIN:
1FT8W3BTXEEA24777

Preparing for a close up...

Photos coming soon

2025 Chevrolet Silverado 2500HD

LTZ Crew Cab 4WD

18,088 miles

$68,000

Good Deal
Prince Frederick, MD
96 mi away
Year:
2025
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:
White
Fuel type:
Biodiesel
Transmission:
Automatic
Mileage:
18,088
Stock number:
P5976A
VIN:
2GC4KPEY6S1130701

Preparing for a close up...

Photos coming soon

2016 Ford F-250 Super Duty

Lariat Crew Cab 4WD

130,468 miles

$29,975

Great Deal
Culpeper, VA
47 mi away
Year:
2016
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
440 hp 6.7L V8 Biodiesel
Exterior color:
Blue
Fuel type:
Biodiesel
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
130,468
VIN:
1FT7W2BT5GEA87035

Preparing for a close up...

Photos coming soon

2021 RAM 1500

Limited Crew Cab 4WD

56,123 miles

$41,500

Fair Deal
Certified Pre-Owned
Woodbridge, VA
61 mi away
Year:
2021
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
260 hp 3L V6 Biodiesel
Exterior color:
Diamond Black Crystal Pearlcoat
Combined gas mileage:
25 MPG
Fuel type:
Biodiesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
56,123
Stock number:
A809829
VIN:
1C6SRFHM0MN809829

Preparing for a close up...

Photos coming soon

2024 RAM 3500

Big Horn Crew Cab LB 4WD

70,794 miles

$49,994

Good Deal
Certified Pre-Owned
Culpeper, VA
49 mi away
Year:
2024
Make:
RAM
Model:
3500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Delmonico Red Pearlcoat
Fuel type:
Diesel
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
70,794
Stock number:
23012A
VIN:
3C63R3HL1RG122711

Preparing for a close up...

Photos coming soon

2018 RAM 2500

Laramie Crew Cab 4WD

119,961 miles

$34,949

Great Deal
Front Royal, VA
14 mi away
Year:
2018
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
350 hp 6.7L I6 Diesel
Exterior color:
Brilliant Black Crystal Pearlcoat
Fuel type:
Diesel
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
119,961
Stock number:
V25370A
VIN:
3C6UR5FL7JG216759

Preparing for a close up...

Photos coming soon

2023 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

18,921 miles

$43,000

Great Deal
Chantilly, VA
42 mi away
Year:
2023
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:
24 MPG
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
18,921
Stock number:
7260175A
VIN:
3GCUDFE8XPG270740

Preparing for a close up...

Photos coming soon

2014 Chevrolet Silverado 2500HD

LTZ Crew Cab 4WD

165,840 miles

$27,900

Fair Deal
Waynesboro, PA
51 mi away
Year:
2014
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
397 hp 6.6L V8 Diesel
Exterior color:
Red (Maroon)
Fuel type:
Diesel
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
165,840
Stock number:
R01001
VIN:
1GC1KYE87EF111886

Preparing for a close up...

Photos coming soon

2014 RAM 2500

Tradesman Crew Cab 4WD

155,863 miles

$25,000

Fair Deal
Mechanicsburg, PA
95 mi away
Year:
2014
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
350 hp 6.7L I6 Diesel
Exterior color:
Gray
Fuel type:
Diesel
Interior color:
Black
Transmission:
Automatic
Mileage:
155,863
Stock number:
EG106842
VIN:
3C6UR5CL0EG106842

Preparing for a close up...

Photos coming soon

2022 Chevrolet Colorado

ZR2 Crew Cab 4WD

74,816 miles

$32,000

Good Deal
Woodbridge, VA
61 mi away
Year:
2022
Make:
Chevrolet
Model:
Colorado
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
181 hp 2.8L I4 Diesel
Exterior color:
Black
Combined gas mileage:
20 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
6-Speed Automatic
Mileage:
74,816
Stock number:
T122205
VIN:
1GCPTEE14N1122205

Preparing for a close up...

Photos coming soon

2015 RAM 1500

Laramie Crew Cab 4WD

106,278 miles

$18,990

Fair Deal
Chantilly, VA
42 mi away
Year:
2015
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
240 hp 3L V6 Biodiesel
Exterior color:
Brilliant Black Crystal Pearlcoat
Combined gas mileage:
23 MPG
Fuel type:
Biodiesel
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
106,278
Stock number:
1073106A
VIN:
1C6RR7NM1FS719344

Preparing for a close up...

Photos coming soon

2020 RAM 3500

Big Horn Crew Cab LB 4WD

92,230 miles

$41,800

Fair Deal
Harrisonburg, VA
67 mi away
Year:
2020
Make:
RAM
Model:
3500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Blue
Fuel type:
Diesel
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
92,230
VIN:
3C63R3HL9LG237838

Preparing for a close up...

Photos coming soon

2011 Ford F-250 Super Duty

Lariat Crew Cab 4WD

154,234 miles

$23,495

Good Deal
Staunton, VA
86 mi away
Year:
2011
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 6.7L V8 Biodiesel
Exterior color:
White
Fuel type:
Biodiesel
Interior color:
Brown (Tan)
Transmission:
6-Speed Automatic
Mileage:
154,234
Stock number:
0825SAG
VIN:
1FT7W2BT2BEA04069

Preparing for a close up...

Photos coming soon

2017 RAM 2500

96,868 miles

$43,000

Fair Deal
Waynesboro, PA
52 mi away
Year:
2017
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Gray (Maximum Steel Metallic Clearcoat)
Fuel type:
Diesel
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
96,868
Stock number:
B34509
VIN:
3C6UR5GL5HG508399

Preparing for a close up...

Photos coming soon

2024 RAM 2500

Laramie Crew Cab 4WD

39,970 miles

$49,997

Good Deal
Sterling, VA
41 mi away
Year:
2024
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Bright White Clearcoat
Fuel type:
Diesel
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
39,970
Stock number:
VP15497
VIN:
3C6UR5FL8RG341135

Preparing for a close up...

Photos coming soon

2016 RAM 2500

Big Horn Crew Cab 4WD

197,400 miles

$19,900

Great Deal
Chambersburg, PA
57 mi away
Year:
2016
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
350 hp 6.7L I6 Diesel
Exterior color:
Brilliant Black Crystal Pearlcoat
Fuel type:
Diesel
Interior color:
Diesel Gray/Black
Transmission:
6-Speed Automatic
Mileage:
197,400
Stock number:
25570
VIN:
3C6UR5DL8GG247708

Preparing for a close up...

Photos coming soon

2020 Chevrolet Silverado 1500

RST Crew Cab 4WD

54,760 miles

$30,888

Great Deal
Cockeysville, MD
84 mi away
Year:
2020
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
277 hp 3L I6 Diesel
Exterior color:
Black
Combined gas mileage:
26 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
54,760
Stock number:
TZ233146A
VIN:
3GCUYEET0LG410954

Preparing for a close up...

Photos coming soon

2024 RAM 2500

Big Horn Crew Cab 4WD

52,822 miles

$44,375

Good Deal
Moorefield, WV
43 mi away
Year:
2024
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
370 hp 6.7L I6 Diesel
Exterior color:
Bright White Clearcoat
Fuel type:
Diesel
Interior color:
Diesel Gray/Black
Transmission:
6-Speed Automatic
Mileage:
52,822
Stock number:
FP3970
VIN:
3C6UR5DL8RG313970

Sponsored

  • Cheap Trucks for Sale in Winchester VA

  • AWD cars for Sale in Winchester VA

  • Cheap SUVs for Sale in Winchester VA

  • Fuel Efficient Cars for Sale in Winchester VA

  • Reliable Cars for Sale in Winchester VA

  • 4X4 trucks for Sale in Winchester VA

  • Ford Trucks for Sale in Winchester VA

  • Chevrolet Trucks For Sale in Winchester VA

  • Dodge Trucks For Sale in Winchester VA

  • Hybrid Cars For Sale in Winchester VA

  • Cars with Online Financing For Sale in Winchester VA

  • Third Row SUVs For Sale in Winchester VA

  • Diesel Trucks for Sale in Hagerstown MD

  • Diesel Trucks for Sale in Cumberland MD

  • Diesel Trucks for Sale in Manassas VA

  • Diesel Trucks for Sale in Harrisonburg VA

  • Diesel Trucks for Sale in Washington DC

  • Diesel Trucks for Sale in Fredericksburg VA

  • Diesel Trucks for Sale in Hanover PA

  • Diesel Trucks for Sale in Charlottesville VA

  • Diesel Trucks for Sale in Baltimore MD

  • 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

  • Kingstowne Motorcars

  • Country Chevrolet, Inc.

  • Lindsay Chrysler Dodge Jeep Ram

  • Car Vault

  • Nine Stars Auto Group

  • AutoNation Honda Dulles

  • Dulles Kia

  • Koons Sterling Ford

  • AutoNation Toyota Leesburg

  • Auto Expo, Inc

  • Auto Galleria LLC

  • Joyce Koons Honda Buick GMC

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.