Best Pickup Trucks For Sale inWinchester, MA
1,963 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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 Crystal Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black/New Saddle
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,040
- Stock #:
- N40982A
- VIN:
- 1C6SRFKT8MN563757
Sponsored by Woburn Toyota
2021 RAM 1500
Limited Longhorn Crew Cab 4WD
61,040 mi
Woburn, MA
4 mi away
Fair Deal
$39,272
- 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:
- 8-Speed Automatic
- Mileage:
- 39,284
- Stock #:
- 91014L
- VIN:
- 3GCPDBEK8PG195084
New arrival
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Crew Cab 4WD
39,284 mi
Hooksett, NH
44 mi away
Fair Deal
$32,870
- 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:
- Delmonico Red Pearlcoat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- Automatic
- Mileage:
- 32,719
- Stock #:
- P3017L
- VIN:
- 1C6RRFFG6PN548853
Sponsored Listing
2023 RAM 1500
Big Horn Crew Cab 4WD
32,719 mi
South Weymouth, MA
20 mi away
Fair Deal
$34,988
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 308 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 77,554
- Stock #:
- C6160
- VIN:
- 1GCGTDEN2M1289402
New arrival
2021 Chevrolet Colorado
Z71 Crew Cab 4WD
77,554 mi
Fitchburg, MA
33 mi away
Good Deal
$26,395
- 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:
- 8-Speed Automatic
- Mileage:
- 86,285
- Stock #:
- PNH1177A
- VIN:
- 3GCPDKEK4PG270430
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
86,285 mi
Portsmouth, NH
44 mi away
Great Deal
$25,494
- 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:
- 27,085
- Stock #:
- UP4469
- VIN:
- 1C6HJTAG1PL519555
2023 Jeep Gladiator
Sport S Crew Cab 4WD
27,085 mi
Haverhill, MA
22 mi away
Fair Deal
$31,461
- Year:
- 2023
- Make:
- Ford
- Model:
- F-250 Super Duty
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 430 hp 7.3L V8
- Exterior color:
- Stone Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 35,381
- Stock #:
- 14578A
- VIN:
- 1FT8X2BN1PED81924
2023 Ford F-250 Super Duty
XLT SuperCab 4WD
35,381 mi
Exeter, NH
39 mi away
Good Deal
$45,586
- Year:
- 2021
- 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
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 136,423
- Stock #:
- 725860
- VIN:
- 1C6RRFBGXMN725860
2021 RAM 1500
Big Horn Quad Cab 4WD
136,423 mi
Rowley, MA
21 mi away
Good Deal
$17,995
- 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:
- 32,060
- Stock #:
- PA3563
- VIN:
- 1GCRDKEK5PZ242466
2023 Chevrolet Silverado 1500
LT Double Cab 4WD
32,060 mi
Amesbury, MA
30 mi away
Good Deal
$32,444
- 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:
- Ivory White Tri-Coat Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 94,809
- Stock #:
- MRT0270
- VIN:
- 1C6SRFJT9NN102425
Price drop
-$1,008
2022 RAM 1500
Laramie Crew Cab 4WD
94,809 mi
Methuen, MA
20 mi away
Fair Deal
$32,407
$31,399
- 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 Crystal Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 76,979
- Stock #:
- JJ11396A
- VIN:
- 1C6SRFFTXMN649226
New arrival
2021 RAM 1500
Big Horn Crew Cab 4WD
76,979 mi
Portsmouth, NH
46 mi away
Good Deal
$29,150
- Year:
- 2022
- 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
- Interior color:
- Unk
- Transmission:
- 9-Speed Automatic
- Mileage:
- 50,351
- Stock #:
- HLP3392A
- VIN:
- 5FPYK3F51NB038290
Price drop
-$551
2022 Honda Ridgeline
RTL AWD
50,351 mi
North Attleboro, MA
36 mi away
Great Deal
$27,779
$27,228
- 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:
- 12,061
- Stock #:
- CC664
- VIN:
- 3GCPDCEK2PG299768
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
12,061 mi
Plymouth, MA
42 mi away
Fair Deal
$40,216
- 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
- Transmission:
- Automatic
- Mileage:
- 79,903
- Stock #:
- 551654
- VIN:
- 1GCPDBEK0NZ551654
2022 Chevrolet Silverado 1500
Custom Crew Cab 4WD
79,903 mi
Peabody, MA
10 mi away
Good Deal
$25,995
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,046
- Stock #:
- 90409
- VIN:
- 3GCUYDED1MG194455
Price drop
-$1,422
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
52,046 mi
Hooksett, NH
44 mi away
Good Deal
$32,289
$30,867
- 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:
- Diamond Black Crystal Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,728
- Stock #:
- 4153A
- VIN:
- 1C6SRFJT0PN580557
2023 RAM 1500
Laramie Crew Cab 4WD
48,728 mi
Portsmouth, NH
46 mi away
Great Deal
$36,792
- 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:
- 49,933
- Stock #:
- P19332A
- VIN:
- 3GCPDFEK8NG510132
New arrival
2022 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
49,933 mi
Mendon, MA
32 mi away
Good Deal
$35,467
- 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:
- White
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic
- Mileage:
- 29,760
- Stock #:
- D71290
- VIN:
- 1FTEX1EP3MKD71290
2021 Ford F-150
XLT SuperCab 4WD
29,760 mi
Framingham, MA
18 mi away
Great Deal
$30,394
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,312
- Stock #:
- 16046A
- VIN:
- 1C6HJTFG5NL108648
Price drop
-$908
2022 Jeep Gladiator
Overland Crew Cab 4WD
59,312 mi
Exeter, NH
39 mi away
Good Deal
$29,405
$28,497
- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,289
- Stock #:
- F78041B
- VIN:
- 3GCPYCEKXNG174177
Price drop
-$1,200
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
88,289 mi
East Providence, RI
45 mi away
Good Deal
$27,415
$26,215
- 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:
- 111,897
- Stock #:
- 26523A
- VIN:
- 1GCPYFED4MZ259257
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
111,897 mi
Londonderry, NH
30 mi away
Good Deal
$27,995
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Fuel type:
- Gasoline
- Transmission:
- 8-Speed Automatic Overdrive
- Mileage:
- 105,135
- Stock #:
- 234539
- VIN:
- 3GCPYBEK0MG234539
2021 Chevrolet Silverado 1500
Custom Crew Cab 4WD
105,135 mi
Nashua, NH
26 mi away
Good Deal
$20,900
- 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:
- Shadow Gray Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,394
- Stock #:
- U9831A
- VIN:
- 1GCUYDED7MZ153005
Price drop
-$674
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
60,394 mi
Brockton, MA
27 mi away
Great Deal
$27,673
$26,999
- 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:
- 8-Speed Automatic
- Mileage:
- 26,662
- Stock #:
- H1422
- VIN:
- 3GCPDKEKXPG342926
Price drop
-$1,595
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
26,662 mi
Hudson, MA
22 mi away
Good Deal
$35,594
$34,594
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