Best Pickup Trucks For Sale inChestertown, MD
921 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,057
- Stock #:
- BC1104
- VIN:
- 1C6RRFFG7PN568898
Sponsored by Ourisman Chrysler Dodge Jeep RAM of Clarksville
2023 RAM 1500
Big Horn Crew Cab 4WD
29,057 mi
Clarksville, MD
47 mi away
Fair Deal
$33,500
- 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:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cement
- Transmission:
- 6-Speed Automatic
- Mileage:
- 48,866
- Stock #:
- 0606A
- VIN:
- 3TMCZ5AN0NM505521
Price drop
-$1,000
Sponsored Listing
2022 Toyota Tacoma
SR5 V6 Double Cab 4WD
48,866 mi
Edgewood, MD
21 mi away
Good Deal
$35,000
$34,000
- 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:
- Silver
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 38,393
- Stock #:
- RGS359968
- VIN:
- 1C6RRFFG2NN359968
New arrival
Sponsored Listing
2022 RAM 1500
Big Horn Crew Cab 4WD
38,393 mi
Hampstead, MD
50 mi away
Good Deal
$30,784
- Year:
- 2023
- Make:
- GMC
- Model:
- Sierra 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
- Transmission:
- Automatic
- Mileage:
- 25,871
- Stock #:
- 15991WP
- VIN:
- 1GTRUJEK3PZ321662
New arrival
2023 GMC Sierra 1500
Elevation Standard Double Cab 4WD
25,871 mi
Penns Grove, NJ
48 mi away
Great Deal
$33,798
- 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:
- Gray (Steel Metallic)
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,052
- Stock #:
- NP277072
- VIN:
- 1GCGTCEN8N1277072
2022 Chevrolet Colorado
LT Crew Cab 4WD
41,052 mi
Towson, MD
32 mi away
Great Deal
$27,200
- 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:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,112
- Stock #:
- NP26615
- VIN:
- 1C6HJTAG5ML613773
2021 Jeep Gladiator
Willys Crew Cab 4WD
62,112 mi
Smyrna, DE
26 mi away
Fair Deal
$28,398
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 2 doors
- Drivetrain:
- 4X2
- Engine:
- 3.3L V6 Flex Fuel Vehicle
- Exterior color:
- Silver Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black W/Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 20,982
- Stock #:
- 174697
- VIN:
- 1FTMF1CB2PKE59063
Price drop
-$1,425
2023 Ford F-150
XL Regular Cab RWD
20,982 mi
Millersville, MD
31 mi away
Great Deal
$27,750
$26,325
- 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:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 46,003
- Stock #:
- G3678A
- VIN:
- 3GCUDEE86PG116746
2023 Chevrolet Silverado 1500
RST Crew Cab 4WD
46,003 mi
Penns Grove, NJ
48 mi away
Good Deal
$38,498
- 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:
- Summit White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 65,793
- Stock #:
- 270001B
- VIN:
- 1GCGTDEN6N1213246
2022 Chevrolet Colorado
Z71 Crew Cab 4WD
65,793 mi
Milford, DE
38 mi away
Great Deal
$28,720
- Year:
- 2023
- Make:
- Nissan
- Model:
- Frontier
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 3.8L V6
- Exterior color:
- Baja Storm
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Steel)
- Transmission:
- 9-Speed Automatic
- Mileage:
- 47,470
- Stock #:
- 602892P
- VIN:
- 1N6ED1EK8PN602892
Price drop
-$900
2023 Nissan Frontier
PRO-4X Crew Cab 4WD
47,470 mi
Pasadena, MD
29 mi away
Good Deal
$33,796
$32,896
- 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:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 50,366
- Stock #:
- P1166303
- VIN:
- 1GCPTDEK7P1166303
Price drop
-$900
2023 Chevrolet Colorado
Z71 Crew Cab 4WD
50,366 mi
Annapolis, MD
30 mi away
Great Deal
$31,600
$30,700
- 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:
- Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,451
- Stock #:
- V1016A
- VIN:
- 1GCGTCEN5N1239329
Price drop
-$1,095
2022 Chevrolet Colorado
LT Crew Cab 4WD
35,451 mi
Bel Air, MD
25 mi away
Good Deal
$29,794
$28,699
- Year:
- 2023
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 26,847
- Stock #:
- 26241A
- VIN:
- 1GTRUAEK9PZ223073
2023 GMC Sierra 1500
Pro Double Cab 4WD
26,847 mi
Glen Burnie, MD
30 mi away
Great Deal
$30,699
- 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:
- Diamond Black
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,213
- Stock #:
- 4647
- VIN:
- 1C6RRFFG0NN426549
2022 RAM 1500
Big Horn Crew Cab 4WD
57,213 mi
Cockeysville, MD
36 mi away
Fair Deal
$31,192
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Silver Ice Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,749
- Stock #:
- AC1887A
- VIN:
- 1GCPYBEK5NZ125639
New arrival
2022 Chevrolet Silverado 1500
Custom Crew Cab 4WD
62,749 mi
Aberdeen, MD
22 mi away
Good Deal
$27,781
- 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:
- 48,413
- Stock #:
- 261309A
- VIN:
- 1GCPDBEK2PZ199082
2023 Chevrolet Silverado 1500
Custom Crew Cab 4WD
48,413 mi
Smyrna, DE
28 mi away
Good Deal
$32,791
- 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:
- Velocity Blue Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 50,102
- Stock #:
- MFB32873
- VIN:
- 1FTFW1E57MFB32873
2021 Ford F-150
XLT SuperCrew 4WD
50,102 mi
Cockeysville, MD
36 mi away
Fair Deal
$36,917
- Year:
- 2023
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 285 hp 3.6L V6
- Exterior color:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 33,902
- Stock #:
- 1261991A
- VIN:
- 1C6HJTFG1PL577352
2023 Jeep Gladiator
Overland Crew Cab 4WD
33,902 mi
Milford, DE
39 mi away
Fair Deal
$34,661
- 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:
- 65,751
- Stock #:
- C1937N
- VIN:
- 3GCPDKEK0PG129015
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
65,751 mi
Glen Burnie, MD
30 mi away
Good Deal
$30,297
- 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:
- Sterling Gray Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 71,370
- Stock #:
- H264643A
- VIN:
- 3GCPDKEK0PG265905
Price drop
-$775
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
71,370 mi
Newark, DE
37 mi away
Great Deal
$30,652
$29,877
- 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:
- 22,944
- Stock #:
- P3621
- VIN:
- 1GCPDKEK9PZ322294
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
22,944 mi
Sykesville, MD
49 mi away
Fair Deal
$34,799
- Year:
- 2022
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- Carbonized Gray Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 72,774
- Stock #:
- 40283A
- VIN:
- 1FTFW1E80NFA42931
2022 Ford F-150
XLT SuperCrew 4WD
72,774 mi
Baltimore, MD
29 mi away
Fair Deal
$34,300
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,186
- Stock #:
- 20139
- VIN:
- 1C6RRFFG0PN676358
2023 RAM 1500
Big Horn Crew Cab 4WD
29,186 mi
Bel Air, MD
27 mi away
Good Deal
$34,900
- 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:
- Black (Obsidian Blue Pearl)
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 90,340
- Stock #:
- F261852A
- VIN:
- 5FPYK3F55MB011012
Sponsored Listing
2021 Honda Ridgeline
RTL AWD
90,340 mi
Hurlock, MD
37 mi away
Good Deal
$26,300
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