Best Pickup Trucks For Sale inChestertown, MD
959 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2022
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 2 doors
- Drivetrain:
- 4X2
- Engine:
- 3.3L V6 Flex Fuel Vehicle
- Exterior color:
- Race Red
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black w/Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 109,245
- Stock #:
- P3526
- VIN:
- 1FTMF1CB8NKE23018
New arrival
Sponsored by Elkton Ford
2022 Ford F-150
XL RWD
109,245 mi
Elkton, MD
30 mi away
Good Deal
$19,299
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- Black Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Dark Slate 40consle
- Transmission:
- Automatic
- Mileage:
- 36,623
- Stock #:
- C1878N
- VIN:
- 1FTFW1E85PKD97118
Sponsored Listing
2023 Ford F-150
XLT SuperCrew 4WD
36,623 mi
Glen Burnie, MD
30 mi away
Good Deal
$38,297
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,674
- Stock #:
- 1261946A
- VIN:
- 1GCPYBEK8NZ179355
Sponsored Listing
2022 Chevrolet Silverado 1500
Custom Crew Cab 4WD
38,674 mi
Milford, DE
39 mi away
Fair Deal
$35,711
- Year:
- 2021
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 325 hp 2.7L V6
- Exterior color:
- Blue Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black/Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 86,081
- Stock #:
- 260690A
- VIN:
- 1FTEW1EP2MFA05025
2021 Ford F-150
Lariat SuperCrew 4WD
86,081 mi
Newark, DE
37 mi away
Good Deal
$34,099
- 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:
- Patriot Blue Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,798
- Stock #:
- 7267050A
- VIN:
- 1C6SRFFTXNN235008
New arrival
2022 RAM 1500
Big Horn Crew Cab 4WD
67,798 mi
Milford, DE
39 mi away
Fair Deal
$36,398
- 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:
- Billet Silver Metallic Clearcoat - PSC
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black - X9
- Transmission:
- Automatic
- Mileage:
- 57,828
- Stock #:
- C23689A
- VIN:
- 1C6RRFFG0NN238159
2022 RAM 1500
Big Horn Crew Cab 4WD
57,828 mi
Quarryville, PA
48 mi away
Fair Deal
$31,655
- 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:
- Diamond Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 39,000
- Stock #:
- N267131A
- VIN:
- 1C6SRFBT4MN527824
Price drop
-$1,860
2021 RAM 1500
Big Horn Quad Cab 4WD
39,000 mi
Smyrna, DE
26 mi away
Good Deal
$34,658
$32,798
- Year:
- 2023
- 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:
- Agate Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Flex Fuel Vehicle
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 88,726
- Stock #:
- F260800A
- VIN:
- 1FTFW1E57PFA79760
2023 Ford F-150
XLT SuperCrew 4WD
88,726 mi
Hurlock, MD
37 mi away
Good Deal
$37,799
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Black
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 31,100
- Stock #:
- 226604
- VIN:
- 1GCUYEED5NZ127333
2022 Chevrolet Silverado 1500
RST Crew Cab 4WD
31,100 mi
Milford, DE
39 mi away
Good Deal
$38,969
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- 4X2
- Engine:
- 200 hp 2.5L I4
- Exterior color:
- Summit White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 63,497
- Stock #:
- P128014A
- VIN:
- 1GCHSCEA2N1121758
New arrival
2022 Chevrolet Colorado
LT Extended Cab RWD
63,497 mi
Bridgeton, NJ
48 mi away
Good Deal
$18,947
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 200 hp 2.5L I4
- Exterior color:
- White
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 61,757
- Stock #:
- 116442
- VIN:
- 1GCHTCEA9N1116442
2022 Chevrolet Colorado
LT Extended Cab 4WD
61,757 mi
Dover, DE
29 mi away
Good Deal
$23,245
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Shadow Gray Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,315
- Stock #:
- N267238A
- VIN:
- 1GCPYDEKXMZ362766
Price drop
-$2,000
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
82,315 mi
Smyrna, DE
26 mi away
Good Deal
$30,398
$28,398
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- 4X2
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,081
- Stock #:
- 260123A
- VIN:
- 1C6RREGT8PN564879
2023 RAM 1500
Tradesman Crew Cab RWD
56,081 mi
Smyrna, DE
28 mi away
Good Deal
$28,159
- Year:
- 2022
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 450 hp 3.5L V6
- Exterior color:
- Silver Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 29,033
- Stock #:
- 826604
- VIN:
- 1FTEW1E86NFC12897
Price drop
-$1,996
2022 Ford F-150
Tremor SuperCrew 4WD
29,033 mi
Milford, DE
39 mi away
Great Deal
$46,793
$44,797
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- Antimatter Blue
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 27,314
- Stock #:
- C260004A
- VIN:
- 1FTFW1E82PFA50273
New arrival
2023 Ford F-150
Platinum SuperCrew 4WD
27,314 mi
Hurlock, MD
37 mi away
Fair Deal
$56,799
- 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:
- Hydro Blue Pearlcoat - PBJ
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black - X9
- Transmission:
- Automatic
- Mileage:
- 85,725
- Stock #:
- C23672A
- VIN:
- 1C6SRFFT1MN786104
Price drop
-$2,503
2021 RAM 1500
Big Horn Crew Cab 4WD
85,725 mi
Quarryville, PA
48 mi away
Good Deal
$30,464
$27,961
- Year:
- 2022
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Diamond Black Crystal Pearlcoat
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 36,187
- Stock #:
- R1727
- VIN:
- 1C6SRFJT4NN457194
Price drop
-$1,000
2022 RAM 1500
Laramie Crew Cab 4WD
36,187 mi
Newark, DE
37 mi away
Good Deal
$40,776
$39,776
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Harvest Bronze Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- Automatic
- Mileage:
- 28,269
- Stock #:
- H8680B2
- VIN:
- 1GCUDGEDXPZ208029
2023 Chevrolet Silverado 1500
LTZ Crew Cab 4WD
28,269 mi
Dover, DE
30 mi away
Good Deal
$44,948
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Bright White Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,772
- Stock #:
- 826132A
- VIN:
- 1C6SRFRT7PN666999
Price drop
-$1,515
2023 RAM 1500
Laramie Crew Cab 4WD
15,772 mi
Milford, DE
39 mi away
Good Deal
$48,311
$46,796
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 260 hp 3L V6 Biodiesel
- Exterior color:
- Patriot Blue Pearlcoat
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Biodiesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 39,330
- Stock #:
- M6937
- VIN:
- 1C6SRFFM8PN539398
2023 RAM 1500
Big Horn Crew Cab 4WD
39,330 mi
Bowie, MD
39 mi away
Good Deal
$36,525
- Year:
- 2023
- Make:
- Toyota
- Model:
- Tacoma
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- 4X2
- Engine:
- 159 hp 2.7L I4
- Exterior color:
- Ice Cap
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cement Gray
- Transmission:
- 6-Speed Automatic
- Mileage:
- 33,289
- Stock #:
- F261143B
- VIN:
- 3TYRX5GN7PT077994
2023 Toyota Tacoma
SR I4 Access Cab RWD
33,289 mi
Hurlock, MD
37 mi away
Great Deal
$27,799
- 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:
- 69,490
- Stock #:
- 226623
- VIN:
- 1GCUDEE84PZ281923
Price drop
-$1,823
2023 Chevrolet Silverado 1500
RST Crew Cab 4WD
69,490 mi
Milford, DE
39 mi away
Great Deal
$39,574
$37,751
- 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
Milford, DE
39 mi away
Good Deal
$32,699
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 3.5L V6 Hybrid
- Exterior color:
- White Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Hybrid
- Interior color:
- Java
- Transmission:
- Automatic
- Mileage:
- 48,173
- Stock #:
- 6B3005A
- VIN:
- 1FTFW1ED7PFB51189
Sponsored Listing
2023 Ford F-150
King Ranch SuperCrew 4WD
48,173 mi
Lanham, MD
46 mi away
Good Deal
$50,448
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