Used Pickup Trucks for Sale nearChestertown, MD
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Silver Ice Metallic
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 9,752
- Stock #:
- 61612A
- VIN:
- 3GCPYFED5NG184599


Sponsored by JBA Chevrolet
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
9,752 mi
$41,797
- 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:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 42,137
- Stock #:
- FGLB29716
- VIN:
- 1FTEW1EP7PFB29716

-$800
Sponsored Listing
2023 Ford F-150
XL SuperCrew 4WD
42,137 mi
$33,598
$32,798
- Year:
- 2021
- 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:
- 8-Speed Automatic
- Mileage:
- 109,732
- Stock #:
- S1588A
- VIN:
- 3GCUYEED9MG252088

-$690
Sponsored Listing
2021 Chevrolet Silverado 1500
RST Crew Cab 4WD
109,732 mi
$27,390
$26,700
- Year:
- 2021
- Make:
- Honda
- Model:
- Ridgeline
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 280 hp 3.5L V6
- Exterior color:
- White
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- 9-Speed Automatic
- Mileage:
- 63,445
- Stock #:
- 613001A
- VIN:
- 5FPYK3F15MB003134

-$2,000
2021 Honda Ridgeline
Sport AWD
63,445 mi
$26,670
$24,670
- Year:
- 2021
- 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, Leather-Appointed Front Seat Trim
- Transmission:
- Automatic
- Mileage:
- 29,674
- Stock #:
- G3782A
- VIN:
- 1GCUYEED0MZ357697

-$1,001
2021 Chevrolet Silverado 1500
RST Crew Cab 4WD
29,674 mi
$36,934
$35,933
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,571
- Stock #:
- N267089A
- VIN:
- 1C6SRFBT2MN783685

2021 RAM 1500
Big Horn Quad Cab 4WD
96,571 mi
$24,794
- Year:
- 2024
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 305 hp 3.6L V6
- Exterior color:
- Crystal Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 44,337
- Stock #:
- NP26064
- VIN:
- 1C6RR7GG8RS148222

2024 RAM 1500
Classic SLT Quad Cab 4WD
44,337 mi
$27,794
- Year:
- 2022
- Make:
- RAM
- Model:
- 3500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 91,671
- Stock #:
- 25368A
- VIN:
- 3C63RRJL5NG153211

2022 RAM 3500
Laramie Crew Cab LB DRW 4WD
91,671 mi
$49,306
- 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
$29,201
- 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
$21,775
- 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:
- Red Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,268
- Stock #:
- 826617
- VIN:
- 1C6HJTFG9ML588496

2021 Jeep Gladiator
Overland Crew Cab 4WD
43,268 mi
$30,512
- Year:
- 2022
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Delmonico Red Pearlcoat - PRV
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black - X9
- Transmission:
- Automatic
- Mileage:
- 7,326
- Stock #:
- P4514
- VIN:
- 1C6SRFJT3NN344658

-$3,537
2022 RAM 1500
Laramie Crew Cab 4WD
7,326 mi
$45,298
$41,761
- Year:
- 2019
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 375 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 108,977
- Stock #:
- G3759A
- VIN:
- 1FTFW1E4XKFD39729

-$1,820
2019 Ford F-150
XLT SuperCrew LB 4WD
108,977 mi
$22,720
$20,900
Popular Pickup Truck reviews
- Year:
- 2020
- Make:
- GMC
- Model:
- Canyon
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 308 hp 3.6L V6
- Exterior color:
- Summit White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 36,910
- Stock #:
- R8896A
- VIN:
- 1GTG6EEN0L1242252

2020 GMC Canyon
Denali Crew Cab 4WD
36,910 mi
$30,710
- 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
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,596
- Stock #:
- 226109
- VIN:
- 1GCGTDEN0N1155103

-$1,073
2022 Chevrolet Colorado
Z71 Crew Cab 4WD
34,596 mi
$32,139
$31,066
- Year:
- 2024
- Make:
- GMC
- Model:
- Sierra 2500HD
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 401 hp 6.6L V8
- Exterior color:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Brown
- Transmission:
- Automatic
- Mileage:
- 80,430
- Stock #:
- 28719435
- VIN:
- 1GT49RE70RF293636

2024 GMC Sierra 2500HD
Denali Crew Cab 4WD
80,430 mi
$56,998
- 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:
- Blue Pearl
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,828
- Stock #:
- LP116978
- VIN:
- 1C6HJTAG1NL116978

2022 Jeep Gladiator
Sport Crew Cab 4WD
55,828 mi
$27,600
- Year:
- 2016
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- True Blue Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,854
- Stock #:
- W6285A
- VIN:
- 1C6RR7LT1GS366437

2016 RAM 1500
Big Horn Crew Cab 4WD
29,854 mi
$20,499
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Glacier Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,816
- Stock #:
- 7267254A
- VIN:
- 1GCPTEEK0P1221518

2023 Chevrolet Colorado
Trail Boss Crew Cab 4WD
57,816 mi
$31,699
- Year:
- 2025
- Make:
- Toyota
- Model:
- Tacoma
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 278 hp 2.4L I4
- Exterior color:
- Celestial Silver Metallic
- Fuel type:
- Gasoline
- Interior color:
- Boulder
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,257
- Stock #:
- T261671A
- VIN:
- 3TMLB5JN1SM088510

2025 Toyota Tacoma
Limited Double Cab 4WD
10,257 mi
$45,799
- Year:
- 2021
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Onyx Black
- Fuel type:
- Gasoline
- Interior color:
- Jet Black, Cloth Seat Trim
- Transmission:
- Automatic
- Mileage:
- 35,750
- Stock #:
- G3779B
- VIN:
- 3GTU9BED1MG188348

2021 GMC Sierra 1500
SLE Crew Cab 4WD
35,750 mi
$32,930
- Year:
- 2019
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3.3L V6 Flex Fuel Vehicle
- Exterior color:
- Oxford White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Medium Earth Gray
- Transmission:
- 6-Speed Automatic
- Mileage:
- 128,415
- Stock #:
- 260193A
- VIN:
- 1FTEX1EB4KFA41801

2019 Ford F-150
XLT SuperCab 4WD
128,415 mi
$18,923
- Year:
- 2020
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Agate Black Metallic
- Interior color:
- Medium Earth Gray
- Transmission:
- Automatic
- Mileage:
- 80,343
- Stock #:
- P10172A
- VIN:
- 1FTEW1E49LFC71694

-$1,208
Sponsored Listing
2020 Ford F-150
XLT SuperCrew 4WD
80,343 mi
$30,554
$29,346
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.
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
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
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.