Best Pickup Trucks For Sale inWindsor, MA
3,623 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 40,131
- Stock #:
- 9763
- VIN:
- 1GCPDBEK7PZ178664
Sponsored by Terryville Chevrolet
2023 Chevrolet Silverado 1500
Custom Crew Cab 4WD
40,131 mi
Terryville, CT
58 mi away
Fair Deal
$36,128
- 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:
- Red Alert
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Sandstone
- Transmission:
- 9-Speed Automatic
- Mileage:
- 31,522
- Stock #:
- 9411U
- VIN:
- 1N6ED1EK7PN604536
Sponsored Listing
2023 Nissan Frontier
SV Crew Cab 4WD
31,522 mi
Fairfield, CT
93 mi away
Fair Deal
$32,708
- 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:
- Cardinal Red
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black With Kalahari Accents
- Transmission:
- Automatic
- Mileage:
- 72,236
- Stock #:
- 26-612A
- VIN:
- 1GTP9EED8MZ236040
Sponsored Listing
2021 GMC Sierra 1500
AT4 Crew Cab 4WD
72,236 mi
Torrington, CT
48 mi away
Fair Deal
$37,976
- 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:
- 1cx
- Transmission:
- 8-Speed Automatic
- Mileage:
- 19,451
- Stock #:
- C2975
- VIN:
- 1GCRDBEK6NZ612403
New arrival
2022 Chevrolet Silverado 1500
Custom Double Cab 4WD
19,451 mi
Danbury, CT
78 mi away
Fair Deal
$32,894
- Year:
- 2023
- 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:
- 84,106
- Stock #:
- C89573CT
- VIN:
- 3C6UR5DL6PG589982
Price drop
-$4,000
2023 RAM 2500
Big Horn Crew Cab 4WD
84,106 mi
Hooksett, NH
90 mi away
Fair Deal
$39,772
$35,772
- 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:
- Firecracker Red Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 45,935
- Stock #:
- TR065115A
- VIN:
- 1C6HJTAG8ML533304
2021 Jeep Gladiator
Willys Crew Cab 4WD
45,935 mi
Claremont, NH
67 mi away
Great Deal
$26,981
- Year:
- 2021
- 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:
- Blue Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Hybrid
- Interior color:
- Black/Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 64,906
- Stock #:
- N160A
- VIN:
- 1FTFW1ED4MFC90479
New arrival
2021 Ford F-150
XLT SuperCrew 4WD
64,906 mi
East Providence, RI
99 mi away
Fair Deal
$35,398
- Year:
- 2021
- Make:
- Nissan
- Model:
- Frontier
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 3.8L V6
- Exterior color:
- Arctic Blue Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Pro-4x
- Transmission:
- 9-Speed Automatic
- Mileage:
- 19,834
- Stock #:
- N1818A
- VIN:
- 1N6ED0EB1MN711135
2021 Nissan Frontier
PRO-4X Crew Cab 4WD
19,834 mi
Bennington, VT
27 mi away
Great Deal
$29,498
- 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
83 mi away
Good Deal
$37,546
- 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:
- Blue
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 45,573
- Stock #:
- CT2898
- VIN:
- 1C6SRFLT5NN179581
2022 RAM 1500
Rebel Crew Cab 4WD
45,573 mi
Colchester, CT
75 mi away
Good Deal
$40,349
- 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:
- Gray
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 11,649
- Stock #:
- PM607835
- VIN:
- 3TMCZ5AN3PM607835
2023 Toyota Tacoma
TRD Off Road Double Cab 4WD
11,649 mi
Kingston, NY
62 mi away
Fair Deal
$41,063
- Year:
- 2023
- Make:
- Ford
- Model:
- F-150
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 450 hp 3.5L V6
- Exterior color:
- White Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 34,449
- Stock #:
- C26081B
- VIN:
- 1FTEW1E80PFB15813
2023 Ford F-150
Tremor SuperCrew 4WD
34,449 mi
Brattleboro, VT
35 mi away
Good Deal
$50,289
- 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:
- Delmonico Red Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,775
- Stock #:
- 26Z134
- VIN:
- 1C6SRFFT2MN693463
2021 RAM 1500
Big Horn Crew Cab 4WD
38,775 mi
Granville, NY
61 mi away
Good Deal
$33,896
- 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:
- 68,460
- Stock #:
- 6849PRC
- VIN:
- 1GCPYBEK8NZ117390
2022 Chevrolet Silverado 1500
Custom Crew Cab 4WD
68,460 mi
Warrensburg, NY
78 mi away
Good Deal
$28,804
- Year:
- 2022
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 395 hp 5.7L V8
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,929
- Stock #:
- 26-313
- VIN:
- 1C6SRFVT8NN359490
2022 RAM 1500
Sport Crew Cab 4WD
61,929 mi
Lowell, MA
87 mi away
Good Deal
$36,893
- Year:
- 2023
- Make:
- Ford
- Model:
- F-250 Super Duty
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 6.7L V8 Biodiesel
- Exterior color:
- Agate Black Metallic
- Fuel type:
- Biodiesel
- Interior color:
- Black Onyx/Carmelo
- Transmission:
- Automatic
- Mileage:
- 32,144
- Stock #:
- U0678
- VIN:
- 1FT7W2BT5PED90686
2023 Ford F-250 Super Duty
Platinum Crew Cab 4WD
32,144 mi
Amsterdam, NY
66 mi away
Good Deal
$69,675
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,383
- Stock #:
- 9458
- VIN:
- 1GCPYJEK8MZ444185
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
22,383 mi
Terryville, CT
58 mi away
Fair Deal
$33,721
- Year:
- 2021
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Onyx Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,199
- Stock #:
- G26033A
- VIN:
- 3GTP9CEKXMG426988
2021 GMC Sierra 1500
Elevation Crew Cab 4WD
82,199 mi
Haverhill, MA
100 mi away
Good Deal
$30,387
- 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:
- Automatic
- Mileage:
- 25,595
- Stock #:
- GB0401
- VIN:
- 3GCPDCEK8PG340310
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
25,595 mi
Carmel, NY
82 mi away
Good Deal
$37,766
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,500
- Stock #:
- CU629390A
- VIN:
- 1C6SRFFT8MN570010
2021 RAM 1500
Big Horn Crew Cab 4WD
36,500 mi
Middletown, CT
70 mi away
Fair Deal
$34,989
- 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:
- Black
- Fuel type:
- Gasoline
- Interior color:
- Black
- Mileage:
- 71,313
- Stock #:
- 547928
- VIN:
- 1C6SRFLT8MN547928
2021 RAM 1500
Rebel Crew Cab 4WD
71,313 mi
Middletown, CT
67 mi away
Good Deal
$36,789
- 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 Clearcoat
- Fuel type:
- Gasoline
- Mileage:
- 39,208
- Stock #:
- 515569
- VIN:
- 1C6HJTAG4NL163633
2022 Jeep Gladiator
Sport S Crew Cab 4WD
39,208 mi
Northampton, MA
24 mi away
Great Deal
$29,588
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 77,304
- Stock #:
- CW60763B
- VIN:
- 1GCPYJEKXMZ413214
Price drop
-$1,000
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
77,304 mi
Warwick, RI
99 mi away
Good Deal
$29,377
$28,377
- 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:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black (Charcoal)
- Transmission:
- Automatic
- Mileage:
- 103,314
- Stock #:
- AM4001
- VIN:
- 1GCUYEED9MZ420537
Sponsored Listing
2021 Chevrolet Silverado 1500
RST Crew Cab 4WD
103,314 mi
Derry, NH
94 mi away
Fair Deal
$29,900
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