Best Pickup Trucks For Sale inCheshire, MA
3,112 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Titanium
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black With Kalahari Accents
- Transmission:
- Automatic
- Mileage:
- 39,380
- Stock #:
- C48938
- VIN:
- 1GTUUEEL4PZ238980
Sponsored by Imperial Chevrolet
2023 GMC Sierra 1500
AT4 Crew Cab 4WD
39,380 mi
Mendon, MA
88 mi away
Fair Deal
$51,967
- 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:
- Black Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 31,413
- Stock #:
- 7T2153
- VIN:
- 1FTEX1EP8PKD99431
Sponsored Listing
2023 Ford F-150
XL SuperCab 4WD
31,413 mi
Albany, NY
34 mi away
Good Deal
$34,950
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 75,413
- Stock #:
- 390926
- VIN:
- 3GCPYFED7MG390926
Sponsored Listing
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
75,413 mi
Fort Montgomery, NY
95 mi away
Great Deal
$31,170
- 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:
- 79,871
- Stock #:
- H60071A
- VIN:
- 3GCPDDEK2PG144255
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
79,871 mi
Hudson, MA
82 mi away
Great Deal
$29,594
- 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:
- Red Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 64,788
- Stock #:
- 26P097
- VIN:
- 1FTFW1E80PFA71977
2023 Ford F-150
Lariat SuperCrew 4WD
64,788 mi
Townsend, MA
73 mi away
Good Deal
$44,018
- 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:
- 65,676
- Stock #:
- 26184B
- VIN:
- 1C6SRFJT5PN577606
2023 RAM 1500
Laramie Crew Cab 4WD
65,676 mi
Fairfield, CT
98 mi away
Great Deal
$35,796
- 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:
- Sting-Gray Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,588
- Stock #:
- L24826A
- VIN:
- 1C6JJTAG9ML573828
2021 Jeep Gladiator
Sport Crew Cab 4WD
75,588 mi
White River Junction, VT
86 mi away
Good Deal
$26,018
- Year:
- 2022
- Make:
- RAM
- Model:
- 2500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 410 hp 6.4L V8
- Exterior color:
- Diamond Black Crystal Pearlcoat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 128,286
- Stock #:
- U2026
- VIN:
- 3C6UR5DJ8NG240849
2022 RAM 2500
Big Horn Crew Cab 4WD
128,286 mi
Milford, CT
93 mi away
Great Deal
$28,029
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Northsky Blue Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 64,639
- Stock #:
- 6713PRA
- VIN:
- 1GCUYEED7NZ105267
2022 Chevrolet Silverado 1500
RST Crew Cab 4WD
64,639 mi
Warrensburg, NY
72 mi away
Good Deal
$34,802
- 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:
- Agate Black Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 59,515
- Stock #:
- N5624
- VIN:
- 1FTEW1EP9MKE27722
Price drop
-$1,000
2021 Ford F-150
XLT SuperCrew 4WD
59,515 mi
Torrington, CT
51 mi away
Good Deal
$33,186
$32,186
- 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:
- Titanium Rush Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 26,935
- Stock #:
- H1441
- VIN:
- 1GTRUBEK2PZ256146
2023 GMC Sierra 1500
SLE Double Cab 4WD
26,935 mi
Hudson, MA
82 mi away
Good Deal
$36,594
- 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:
- Black
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 93,410
- Stock #:
- ELA49867A
- VIN:
- 1GCPYFED7MZ191021
Price drop
-$1,849
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,410 mi
Watertown, CT
68 mi away
Fair Deal
$33,648
$31,799
- 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:
- Sting-Gray Clear Coat
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 11,004
- Stock #:
- 7565UJG
- VIN:
- 1C6JJTEG1NL177565
2022 Jeep Gladiator
Mojave Crew Cab 4WD
11,004 mi
Ware, MA
51 mi away
Fair Deal
$39,344
- 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:
- 8-Speed Automatic
- Mileage:
- 53,974
- Stock #:
- CU4195A
- VIN:
- 1C6SRFRM7NN247833
New arrival
2022 RAM 1500
Laramie Crew Cab 4WD
53,974 mi
Beacon, NY
84 mi away
Fair Deal
$38,599
- Year:
- 2021
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 400 hp 3.5L V6
- Exterior color:
- Brown
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Java
- Transmission:
- Automatic
- Mileage:
- 93,410
- Stock #:
- P1388A
- VIN:
- 1FTFW1E84MFC01738
2021 Ford F-150
King Ranch SuperCrew 4WD
93,410 mi
Madison, CT
92 mi away
Great Deal
$34,611
- 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:
- Radiant Red Tintcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 44,976
- Stock #:
- N6357A
- VIN:
- 1GCUDDED8PZ206245
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
44,976 mi
Nashua, NH
87 mi away
Good Deal
$36,675
- 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:
- 70,605
- Stock #:
- HH1108M
- VIN:
- 1GCPYBEK7MZ301542
2021 Chevrolet Silverado 1500
Custom Crew Cab 4WD
70,605 mi
Bow, NH
92 mi away
Good Deal
$27,144
- 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:
- Sarge Green Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 43,282
- Stock #:
- E5948
- VIN:
- 1C6HJTAG9PL563898
Price drop
-$1,100
2023 Jeep Gladiator
Sport S Crew Cab 4WD
43,282 mi
Putnam, CT
79 mi away
Great Deal
$29,492
$28,392
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 33,091
- Stock #:
- L26G14A
- VIN:
- 1C6HJTFG7PL534974
2023 Jeep Gladiator
High Altitude Crew Cab 4WD
33,091 mi
Latham, NY
34 mi away
Good Deal
$35,108
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,041
- Stock #:
- U0907
- VIN:
- 1GCRDDEK3NZ518104
New arrival
2022 Chevrolet Silverado 1500
LT Double Cab 4WD
61,041 mi
Amsterdam, NY
61 mi away
Fair Deal
$29,400
- Year:
- 2023
- Make:
- Toyota
- Model:
- Tacoma
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 278 hp 3.5L V6
- Exterior color:
- Lunar Rock
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black/Gun Metal
- Transmission:
- 6-Speed Automatic
- Mileage:
- 47,604
- Stock #:
- 2338556
- VIN:
- 3TMCZ5AN4PM538556
2023 Toyota Tacoma
TRD Sport Double Cab 4WD
47,604 mi
Rutland, VT
72 mi away
Good Deal
$38,646
- 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:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 74,992
- Stock #:
- H1377A
- VIN:
- 1GCRDBEKXPZ253849
2023 Chevrolet Silverado 1500
Custom Double Cab 4WD
74,992 mi
Hudson, MA
82 mi away
Good Deal
$28,594
- 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:
- Ceramic Gray Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 7,228
- Stock #:
- 26Z240
- VIN:
- 1C6SRFLT3PN670900
New arrival
2023 RAM 1500
Rebel Crew Cab 4WD
7,228 mi
Granville, NY
58 mi away
Fair Deal
$52,696
- 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:
- Olive Green Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,815
- Stock #:
- Z4717
- VIN:
- 1C6SRFJT7MN739084
Sponsored Listing
2021 RAM 1500
Laramie Crew Cab 4WD
56,815 mi
Brookfield, CT
77 mi away
Good Deal
$34,986
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