Best Pickup Trucks For Sale inWinchester, MA
2,004 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:
- 305 hp 3.6L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 115,307
- Stock #:
- 556916
- VIN:
- 1C6RR7GG9MS556916
Sponsored by Auto Factory
2021 RAM 1500
Classic Warlock Quad Cab 4WD
115,307 mi
Peabody, MA
10 mi away
Good Deal
$20,900
- 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:
- Avalanche
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 37,447
- Stock #:
- MP8193
- VIN:
- 1FTEW1EP3PKD49832
Sponsored Listing
2023 Ford F-150
XLT SuperCrew 4WD
37,447 mi
Exeter, NH
39 mi away
Good Deal
$39,830
- 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:
- Oxford White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 20,042
- Stock #:
- PT3802
- VIN:
- 1FTFW1E84PFA71223
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Sponsored Listing
2023 Ford F-150
XLT SuperCrew 4WD
20,042 mi
Foxboro, MA
25 mi away
Fair Deal
$46,797
- Year:
- 2022
- Make:
- GMC
- Model:
- Sierra 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:
- Gray
- Transmission:
- Automatic
- Mileage:
- 51,418
- Stock #:
- 14843
- VIN:
- 3GTUUGED2NG672154
2022 GMC Sierra 1500
Denali Crew Cab 4WD
51,418 mi
North Smithfield, RI
38 mi away
Good Deal
$46,409
- 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:
- White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 43,831
- Stock #:
- 25P044
- VIN:
- 1FTFW1E85NFB01164
2022 Ford F-150
Limited SuperCrew 4WD
43,831 mi
Townsend, MA
33 mi away
Good Deal
$49,117
- 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:
- Black
- Fuel type:
- Biodiesel
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 26,500
- Stock #:
- C19292
- VIN:
- 1FT7W2BT2PED79788
2023 Ford F-250 Super Duty
XLT Crew Cab 4WD
26,500 mi
Mendon, MA
32 mi away
Fair Deal
$58,967
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 29,777
- Stock #:
- D16086
- VIN:
- 1C6HJTAG5ML616821
2021 Jeep Gladiator
Willys Crew Cab 4WD
29,777 mi
Mendon, MA
32 mi away
Good Deal
$29,967
- Year:
- 2023
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- 4X2
- Exterior color:
- Bright White Clearcoat
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 114,504
- Stock #:
- B8262
- VIN:
- 1C6RREGT4PN534715
2023 RAM 1500
Tradesman Crew Cab RWD
114,504 mi
Danvers, MA
12 mi away
Good Deal
$20,896
- 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:
- Bright White Clearcoat
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 53,519
- Stock #:
- JJ11400
- VIN:
- 1C6RRFCG8NN212297
Price drop
-$1,000
2022 RAM 1500
Tradesman Quad Cab 4WD
53,519 mi
Portsmouth, NH
46 mi away
Great Deal
$26,898
$25,898
- 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:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,711
- Stock #:
- J26215A
- VIN:
- 1C6RR7GG0NS190801
New arrival
2022 RAM 1500
Classic Warlock Quad Cab 4WD
10,711 mi
Lowell, MA
14 mi away
Fair Deal
$34,588
- 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:
- Oxford White
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black W/Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 61,099
- Stock #:
- C88783L
- VIN:
- 1FTEW1EP0PKE95749
Price drop
-$1,900
2023 Ford F-150
Lariat SuperCrew 4WD
61,099 mi
Hooksett, NH
44 mi away
Great Deal
$38,672
$36,772
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Northsky Blue Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 67,785
- Stock #:
- 88162L
- VIN:
- 1GCUYEET6MZ355847
Price drop
-$1,400
2021 Chevrolet Silverado 1500
RST Crew Cab 4WD
67,785 mi
Hooksett, NH
44 mi away
Great Deal
$32,172
$30,772
- 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:
- Black
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown
- Transmission:
- 8-Speed Automatic
- Mileage:
- 68,230
- Stock #:
- 227111
- VIN:
- 1C6RRFGG7NN227111
2022 RAM 1500
Tradesman Crew Cab 4WD
68,230 mi
Middleboro, MA
42 mi away
Fair Deal
$26,935
- 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:
- 46,490
- Stock #:
- L477923
- VIN:
- 1C6SRFFT2NN477923
2022 RAM 1500
Big Horn Crew Cab 4WD
46,490 mi
Auburn, MA
39 mi away
Good Deal
$34,078
- 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:
- Black
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black X9
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,584
- Stock #:
- MN776313
- VIN:
- 1C6RRFFG2MN776313
2021 RAM 1500
Big Horn Crew Cab 4WD
85,584 mi
Methuen, MA
20 mi away
Fair Deal
$27,190
- 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
New arrival
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
60,394 mi
Brockton, MA
27 mi away
Fair Deal
$34,180
- 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:
- Snazzberry Pearlcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,326
- Stock #:
- 16653P
- VIN:
- 1C6HJTAG0ML587230
2021 Jeep Gladiator
Willys Crew Cab 4WD
62,326 mi
Hanover, MA
27 mi away
Good Deal
$27,427
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 420 hp 6.2L V8
- Exterior color:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 109,511
- Stock #:
- 5061
- VIN:
- 3GCPYFEL3MG145581
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
109,511 mi
Seekonk, MA
45 mi away
Good Deal
$31,494
- 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:
- 46,024
- Stock #:
- 48646A
- VIN:
- 3GCPYBEK3NG111805
2022 Chevrolet Silverado 1500
Custom Crew Cab 4WD
46,024 mi
Mendon, MA
28 mi away
Good Deal
$31,467
- 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:
- Gray (Modern Steel Metallic)
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 9-Speed Automatic
- Mileage:
- 47,564
- Stock #:
- PV3168
- VIN:
- 5FPYK3F59MB009618
2021 Honda Ridgeline
RTL AWD
47,564 mi
Natick, MA
15 mi away
Fair Deal
$28,999
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 54,130
- Stock #:
- PS874A
- VIN:
- 1C6SRFBT6MN775010
2021 RAM 1500
Big Horn Quad Cab 4WD
54,130 mi
Salisbury, MA
30 mi away
Good Deal
$29,621
- Year:
- 2023
- 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
- Mileage:
- 20,678
- Stock #:
- N0900780A
- VIN:
- 5FPYK3F54PB035399
2023 Honda Ridgeline
RTL AWD
20,678 mi
Westford, MA
16 mi away
Great Deal
$32,927
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 3L I6 Diesel
- Exterior color:
- Dark Ash Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Jet Black/Nightshift Blue
- Transmission:
- Automatic
- Mileage:
- 81,195
- Stock #:
- PA12007
- VIN:
- 3GCUDJE81PG107848
2023 Chevrolet Silverado 1500
High Country Crew Cab 4WD
81,195 mi
Manchester, NH
38 mi away
Great Deal
$38,854
- 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:
- 30,105
- Stock #:
- VP5872
- VIN:
- 3GCPDBEK1PG222223
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Crew Cab 4WD
30,105 mi
Haverhill, MA
22 mi away
Fair Deal
$35,973
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