Best Pickup Trucks For Sale in Chester, MA

2023 Ford F-250 Super Duty

XL Crew Cab 4WD

14,300 miles

$48,350

Good Deal

Wilbraham, MA

27 mi away

Year:: 2023
Make:: Ford
Model:: F-250 Super Duty
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 6.8L V8
Exterior color:: Oxford White
Fuel type:: Gasoline
Interior color:: Medium Dark Slate
Transmission:: Automatic
Mileage:: 14,300
Stock number:: F82476A
VIN:: 1FT8W2BA7PEC53235

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2021 GMC Sierra 1500

Elevation Crew Cab 4WD

88,584 miles

$29,114

Great Deal

Certified Pre-Owned

Glastonbury, CT

44 mi away

Year:: 2021
Make:: GMC
Model:: Sierra 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 277 hp 3L I6 Diesel
Exterior color:: Summit White
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 88,584
Stock number:: 21UC8942
VIN:: 3GTU9CET9MG183296

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2023 Toyota Tacoma

TRD Pro Double Cab 4WD

57,087 miles

$41,800

Fair Deal

Bristol, CT

40 mi away

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:: Black
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic
Mileage:: 57,087
Stock number:: UA38075A
VIN:: 3TYCZ5AN3PT167216

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2021 GMC Sierra 1500

Elevation Crew Cab 4WD

41,653 miles

$34,995

Good Deal

Holyoke, MA

19 mi away

Year:: 2021
Make:: GMC
Model:: Sierra 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 277 hp 3L I6 Diesel
Exterior color:: Gray (Satin Steel Metallic)
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 41,653
Stock number:: AT10481A
VIN:: 3GTU9CET1MG307528

2021 RAM 1500

Big Horn Quad Cab 4WD

89,791 miles

$25,997

Fair Deal

Bennington, VT

45 mi away

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
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 89,791
Stock number:: UV4393
VIN:: 1C6SRFBT9MN726979

2021 GMC Sierra 1500

Elevation Crew Cab 4WD

88,584 miles

$29,114

Great Deal

Certified Pre-Owned

Glastonbury, CT

44 mi away

Year:: 2021
Make:: GMC
Model:: Sierra 1500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 277 hp 3L I6 Diesel
Exterior color:: Summit White
Combined gas mileage:: 24 MPG
Fuel type:: Diesel
Interior color:: Black
Transmission:: Automatic
Mileage:: 88,584
Stock number:: 21UC8942
VIN:: 3GTU9CET9MG183296

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2023 Ford Maverick

XLT SuperCrew AWD

45,677 miles

$23,568

Great Deal

New Britain, CT

44 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 RAM 1500

Big Horn Crew Cab 4WD

17,981 miles

$33,995

Good Deal

Certified Pre-Owned

Cheshire, MA

22 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:: White
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: Automatic
Mileage:: 17,981
Stock number:: R23-3338L
VIN:: 1C6RRFFG5PN519957

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2022 Toyota Tacoma

SR5 I4 Double Cab RWD

26,928 miles

$25,619

Great Deal

Bristol, CT

41 mi away

Year:: 2022
Make:: Toyota
Model:: Tacoma
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: 4X2
Engine:: 159 hp 2.7L I4
Exterior color:: Blue
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Black/Gun Metal
Transmission:: 6-Speed Automatic
Mileage:: 26,928
Stock number:: CC2943
VIN:: 3TYAX5GN6NT046407

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

73,086 miles

$29,838

Great Deal

Hudson, NY

38 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:: Shadow Gray Metallic
Combined gas mileage:: 15 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 6-Speed Automatic Overdrive
Mileage:: 73,086
Stock number:: 2200P
VIN:: 1GCPYCEF7MZ408339

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2021 Toyota Tacoma

SR5 V6 Double Cab 4WD

12,678 miles

$32,282

Great Deal

Brattleboro, VT

47 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:: Gray
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Transmission:: 6-Speed Automatic
Mileage:: 12,678
Stock number:: G26114A
VIN:: 3TMCZ5AN4MM446231

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2022 Honda Ridgeline

RTL-E AWD

42,737 miles

$29,957

Good Deal

Certified Pre-Owned

Cheshire, MA

22 mi away

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:: Black
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 42,737
Stock number:: H25639AL
VIN:: 5FPYK3F77NB031152

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2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

20,032 miles

$47,787

Good Deal

Vernon Rockville, CT

38 mi away

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:: Black
Fuel type:: Gasoline
Interior color:: Jet Black/Umber
Transmission:: Automatic
Mileage:: 20,032
Stock number:: ST9380A
VIN:: 2GCUDJED6P1144707

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2022 Jeep Gladiator

Willys Crew Cab 4WD

3,603 miles

$35,995

Fair Deal

Certified Pre-Owned

Cheshire, MA

22 mi away

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:: Gray
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 3,603
Stock number:: CT-6269AL
VIN:: 1C6HJTAGXNL155925

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2021 RAM 1500

Big Horn Quad Cab 4WD

56,310 miles

$28,271

Good Deal

Lenox, MA

17 mi away

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:: Billet Silver Metallic Clearcoat
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 56,310
Stock number:: M3810
VIN:: 1C6SRFBTXMN831496

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2021 Jeep Gladiator

Overland Crew Cab 4WD

87,399 miles

$24,995

Good Deal

Ware, MA

39 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:: Blue
Fuel type:: Gasoline
Mileage:: 87,399
Stock number:: 0390UJG
VIN:: 1C6HJTFG5ML520390

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2023 RAM 1500

Big Horn Crew Cab 4WD

43,001 miles

$32,179

Good Deal

Hudson, NY

38 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:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 21 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 43,001
Stock number:: 2225P
VIN:: 1C6RRFFG9PN666668

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2021 RAM 1500

Big Horn Crew Cab 4WD

56,610 miles

$29,500

Good Deal

Berlin, CT

46 mi away

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:: 56,610
Stock number:: G12762A
VIN:: 1C6SRFFT4MN696283

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2023 GMC Sierra 1500

Elevation Standard Crew Cab 4WD

50,360 miles

$35,412

Good Deal

Certified Pre-Owned

Springfield, MA

24 mi away

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:: Dynamic Blue Metallic
Combined gas mileage:: 19 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 50,360
Stock number:: C50748A
VIN:: 1GTPUJEK1PZ143659

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2021 RAM 2500

Big Horn Crew Cab 4WD

97,802 miles

$31,877

Fair Deal

Palmer, MA

34 mi away

Year:: 2021
Make:: RAM
Model:: 2500
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 410 hp 6.4L V8
Exterior color:: Billet Silver Metallic Clearcoat
Fuel type:: Gasoline
Transmission:: 8-Speed Automatic
Mileage:: 97,802
Stock number:: V16122A
VIN:: 3C6UR5DJ2MG555791

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2021 RAM 1500

Laramie Crew Cab 4WD

60,625 miles

$34,400

Fair Deal

Certified Pre-Owned

Watertown, CT

49 mi away

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:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 60,625
Stock number:: F1579571M
VIN:: 1C6SRFJT4MN621428

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2022 Toyota Tacoma

TRD Off Road Double Cab LB 4WD

46,701 miles

$35,303

Good Deal

Greenfield, MA

29 mi away

Year:: 2022
Make:: Toyota
Model:: Tacoma
Body type:: Pickup Truck
Doors:: 4 doors
Drivetrain:: Four-Wheel Drive
Engine:: 278 hp 3.5L V6
Exterior color:: Army Green
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black/Gun Metal
Transmission:: 6-Speed Automatic
Mileage:: 46,701
Stock number:: T2272AA
VIN:: 3TMDZ5BN7NM126101

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2023 Ford F-150

XLT SuperCrew 4WD

23,934 miles

$37,980

Great Deal

West Sand Lake, NY

41 mi away

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:: Gray (Carbonized Grey Metallic)
Combined gas mileage:: 20 MPG
Fuel type:: Gasoline
Interior color:: Black w/Medium Dark Slate
Transmission:: Automatic
Mileage:: 23,934
Stock number:: 9376
VIN:: 1FTFW1E88PKF02718

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2022 RAM 1500

Limited Crew Cab 4WD

21,321 miles

$46,987

Fair Deal

Chicopee, MA

21 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:: Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:: 18 MPG
Fuel type:: Gasoline
Interior color:: Blue (Indigo/Sea Salt)
Transmission:: 8-Speed Automatic
Mileage:: 21,321
Stock number:: P8251
VIN:: 1C6SRFHT3NN290512

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