Best Pickup Trucks For Sale in Winchendon, MA

2023 Jeep Gladiator

High Altitude Crew Cab 4WD

46,825 miles

$31,000

Good Deal

Framingham, MA

40 mi away

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:: 8-Speed Automatic
Mileage:: 46,825
Stock number:: 564106T
VIN:: 1C6HJTFG9PL564106

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2021 Jeep Gladiator

Overland Crew Cab 4WD

37,764 miles

$28,394

Great Deal

Abington, MA

68 mi away

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:: 37,764
Stock number:: 29704
VIN:: 1C6HJTFG2ML547885

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2022 Chevrolet Silverado 1500

RST Crew Cab 4WD

52,916 miles

$39,883

Fair Deal

Certified Pre-Owned

Norwich, CT

80 mi away

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 277 hp 3L I6 Diesel
Exterior color:: Dark Ash Metallic
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Jet Black
Transmission:: Automatic
Mileage:: 52,916
Stock number:: 13581
VIN:: 1GCUDEET2NZ584426

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2021 Jeep Gladiator

Willys Crew Cab 4WD

35,303 miles

$28,999

Good Deal

Rochester, NH

70 mi away

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:: 35,303
Stock number:: JJ10811
VIN:: 1C6HJTAG0ML576258

2021 GMC Sierra 1500

SLT Crew Cab 4WD

106,388 miles

$28,700

Great Deal

Certified Pre-Owned

Arundel, ME

93 mi away

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:: Summit White
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 106,388
Stock number:: G25182D
VIN:: 1GTU9DED2MZ217559

2023 RAM 1500

Big Horn Crew Cab 4WD

51,623 miles

$32,000

Great Deal

Certified Pre-Owned

Clifton Park, NY

89 mi away

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:: Hydro Blue Pearlcoat
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Diesel Gray/Black
Transmission:: 8-Speed Automatic
Mileage:: 51,623
Stock number:: 12UPN566511
VIN:: 1C6SRFFT4PN566511

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2023 RAM 1500

Big Horn Crew Cab 4WD

49,863 miles

$28,495

Great Deal

White River Junction, VT

70 mi away

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:: Bright White Clearcoat
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 49,863
Stock number:: K7904
VIN:: 1C6RRFFG0PN540280

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2022 GMC Sierra 1500

Elevation Crew Cab 4WD

25,805 miles

$42,553

Good Deal

Greenwich, NY

80 mi away

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:: Dynamic Blue Metallic
Combined gas mileage:: 17 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 25,805
Stock number:: GP1046
VIN:: 1GTUUCED6NZ607123

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2022 RAM 1500

Big Horn Crew Cab 4WD

32,818 miles

$34,900

Great Deal

Clifton Park, NY

89 mi away

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:: Diamond Black Crystal Pearlcoat
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 32,818
Stock number:: 12UNN477637
VIN:: 1C6SRFFT1NN477637

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2021 Ford F-150

Platinum SuperCrew 4WD

50,972 miles

$44,650

Fair Deal

Norwood, MA

54 mi away

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:: Star White Metallic Tri-Coat
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 50,972
Stock number:: G260110A
VIN:: 1FTFW1E8XMFA55541

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2022 RAM 1500

Laramie Crew Cab 4WD

41,680 miles

$35,495

Great Deal

Rochester, NH

70 mi away

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:: Bright White Clearcoat
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 41,680
Stock number:: RC21828A
VIN:: 1C6SRFJT3NN474133

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2021 Chevrolet Silverado 1500

Custom Crew Cab 4WD

59,817 miles

$24,999

Great Deal

Glens Falls, NY

92 mi away

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, Cloth Seat Trim
Transmission:: Automatic
Mileage:: 59,817
Stock number:: TR25299
VIN:: 3GCPYBEK7MG331947

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2022 GMC Sierra 1500

AT4 Crew Cab 4WD

56,994 miles

$45,500

Fair Deal

Norwood, MA

54 mi away

Year:: 2022
Make:: GMC
Model:: Sierra 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 420 hp 6.2L V8
Exterior color:: Onyx Black
Combined gas mileage:: 16 MPG
Fuel type:: Gasoline
Interior color:: Jet Black with Kalahari accents
Transmission:: Automatic
Mileage:: 56,994
Stock number:: G260103A
VIN:: 1GTPUEEL4NZ644218

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2021 Toyota Tacoma

TRD Sport Double Cab LB 4WD

48,820 miles

$35,500

Fair Deal

Norwood, MA

54 mi away

Year:: 2021
Make:: Toyota
Model:: Tacoma
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 278 hp 3.5L V6
Exterior color:: Barcelona Red Metallic
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black/Gun Metal
Transmission:: 6-Speed Automatic
Mileage:: 48,820
Stock number:: G260141A
VIN:: 3TMDZ5BN4MM114504

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2022 Chevrolet Silverado 1500

LT Crew Cab 4WD

12,634 miles

$32,250

Great Deal

White River Junction, VT

69 mi away

Year:: 2022
Make:: Chevrolet
Model:: Silverado 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Exterior color:: Red Hot
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 12,634
Stock number:: C61982A
VIN:: 3GCPYDEK6NG190480

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2021 Jeep Gladiator

Sport Crew Cab 4WD

55,405 miles

$24,499

Good Deal

Rochester, NH

70 mi away

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:: Billet Silver Metallic Clearcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Manual
Mileage:: 55,405
Stock number:: RC21937A
VIN:: 1C6HJTAGXML506346

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2023 Ford Maverick

XLT SuperCrew AWD

45,677 miles

$23,466

Great Deal

New Britain, CT

79 mi away

Year:: 2023
Make:: Ford
Model:: Maverick
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 250 hp 2L I4
Exterior color:: Oxford White - YZ
Combined gas mileage:: 25 MPG
Fuel type:: Gasoline
Interior color:: Blue (Navy Pier/Medium Slate - 7B)
Transmission:: Automatic
Mileage:: 45,677
Stock number:: H9944A
VIN:: 3FTTW8F91PRA52621

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2023 Chevrolet Colorado

Trail Boss Crew Cab 4WD

44,833 miles

$32,999

Good Deal

Hudson, MA

31 mi away

Year:: 2023
Make:: Chevrolet
Model:: Colorado
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 310 hp 2.7L I4
Exterior color:: Radiant Red Tintcoat
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Jet Black
Transmission:: 8-Speed Automatic
Mileage:: 44,833
Stock number:: H1337
VIN:: 1GCPTEEK8P1138340

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2022 Ford F-150

Lariat SuperCrew 4WD

43,096 miles

$38,998

Good Deal

Weymouth, MA

66 mi away

Year:: 2022
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
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 43,096
Stock number:: SB16039
VIN:: 1FTEW1EP7NFB16039

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2021 Ford F-150

XLT SuperCrew 4WD

79,980 miles

$27,246

Great Deal

Putnam, CT

53 mi away

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:: Iconic Silver Metallic
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Black/Medium Dark Slate
Transmission:: Automatic
Mileage:: 79,980
Stock number:: 4380AT
VIN:: 1FTEW1EP4MKD36809

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2022 RAM 2500

Big Horn Crew Cab 4WD

53,134 miles

$36,687

Good Deal

Columbia, CT

66 mi away

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:: Gray (Granite Crystal Metallic Clearcoat)
Fuel type:: Gasoline
Interior color:: Diesel Gray/Black
Transmission:: 8-Speed Automatic
Mileage:: 53,134
Stock number:: D1198K
VIN:: 3C6UR5DJXNG267227

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2022 Chevrolet Silverado 1500

Custom Crew Cab 4WD

24,643 miles

$32,999

Good Deal

Certified Pre-Owned

Glens Falls, NY

92 mi away

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:: Northsky Blue Metallic
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Jet Black, Cloth Seat Trim
Transmission:: Automatic
Mileage:: 24,643
Stock number:: SP25321
VIN:: 3GCPYBEK0NG218648

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2023 RAM 1500

Big Horn Crew Cab 4WD

28,348 miles

$35,998

Good Deal

Salisbury, MA

60 mi away

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:: Red
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Transmission:: 8-Speed Automatic
Mileage:: 28,348
Stock number:: S7417A
VIN:: 1C6SRFFT0PN648025

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2021 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

86,189 miles

$32,647

Good Deal

Milford, MA

45 mi away

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:: Black
Transmission:: Automatic
Mileage:: 86,189
Stock number:: TP5953A
VIN:: 3GCPYFED1MG175753

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