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Best Pickup Trucks For Sale in Windsor, MA

3,281 results
Windsor, MA
2021 Chevrolet Silverado 1500 Custom Crew Cab 4WD Acton Toyota of Littleton

2021 Chevrolet Silverado 1500

Custom Crew Cab 4WD

58,567 miles

$27,655

Good Deal
Littleton, MA
80 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:
Black
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
58,567
Stock number:
S267436C
VIN:
1GCPYBEK9MZ329164

Sponsored

2023 Chevrolet Silverado 1500 LT Crew Cab 4WD

2023 Chevrolet Silverado 1500

LT Crew Cab 4WD

28,409 miles

$37,987

Fair Deal
Certified Pre-Owned
Concord, NH
91 mi away
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:
28,409
Stock number:
T29306
VIN:
1GCPDKEK0PZ129306

Sponsored

2022 RAM 1500 Big Horn Crew Cab 4WD

2022 RAM 1500

Big Horn Crew Cab 4WD

29,989 miles

$31,417

Great Deal
Brattleboro, VT
36 mi away
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:
Silver
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
29,989
Stock number:
P1075
VIN:
1C6RRFFG8NN297542

Sponsored

2023 Toyota Tacoma Trail Edition Double Cab 4WD

2023 Toyota Tacoma

Trail Edition Double Cab 4WD

36,974 miles

$36,000

Great Deal
Claremont, NH
68 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:
36,974
Stock number:
ZP664
VIN:
3TMCZ5AN9PM535765

2023 Toyota Tacoma Limited Double Cab 4WD

2023 Toyota Tacoma

Limited Double Cab 4WD

32,120 miles

$37,495

Great Deal
Shrewsbury, MA
72 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:
Magnetic Gray Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
32,120
Stock number:
10769P
VIN:
3TYGZ5AN5PT143484

2023 RAM 2500 Laramie Crew Cab 4WD

2023 RAM 2500

Laramie Crew Cab 4WD

57,680 miles

$43,046

Great Deal
Greenwich, NY
47 mi away
Year:
2023
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
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
57,680
Stock number:
260034E
VIN:
3C6UR5FJ2PG634959

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2023 RAM 1500

Big Horn Crew Cab 4WD

13,881 miles

$36,999

Good Deal
Bennington, VT
27 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:
Billet Silver Metallic Clearcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
13,881
Stock number:
CH9313A
VIN:
1C6RRFFG7PN569954

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2021 RAM 1500

Limited Crew Cab 4WD

61,141 miles

$37,995

Good Deal
Worcester, MA
68 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:
White (Ivory Tri-Coat Pearl)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
61,141
Stock number:
65136
VIN:
1C6SRFHT9MN514963

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2021 Chevrolet Silverado 1500

Custom Crew Cab 4WD

35,663 miles

$29,500

Good Deal
Albany, NY
41 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:
Shadow Gray Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
35,663
Stock number:
43553
VIN:
1GCPYBEK4MZ219753

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2022 Jeep Gladiator

Willys Crew Cab 4WD

40,067 miles

$26,297

Great Deal
Bridgeport, CT
91 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:
Sarge Green Clearcoat
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
40,067
Stock number:
B26034A2
VIN:
1C6HJTAG9NL115304

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2023 Ford F-150

XLT SuperCrew 4WD

23,743 miles

$38,450

Good Deal
Lowell, MA
86 mi away
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:
Iconic Silver Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,743
Stock number:
F2808
VIN:
1FTEW1EP7PKE04282

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2021 RAM 1500

Big Horn Quad Cab 4WD

68,665 miles

$26,486

Good Deal
Clifton Park, NY
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:
Flame Red Clear Coat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Diesel Gray/Black
Transmission:
8-Speed Automatic
Mileage:
68,665
Stock number:
12UMN818226
VIN:
1C6SRFBT4MN818226

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2022 RAM 1500

Limited Crew Cab 4WD

52,649 miles

$39,950

Great Deal
Albany, NY
39 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:
52,649
Stock number:
2T1572
VIN:
1C6SRFHT5NN176155

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2021 Chevrolet Silverado 1500

RST Crew Cab 4WD

88,671 miles

$26,999

Great Deal
Hudson, MA
76 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:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
88,671
Stock number:
H60205A
VIN:
1GCUYEED9MZ205725

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2023 RAM 1500

Big Horn Crew Cab 4WD

29,156 miles

$37,720

Fair Deal
Certified Pre-Owned
Warrensburg, NY
78 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:
29,156
Stock number:
6948LP
VIN:
1C6RRFFGXPN701976

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2023 Ford F-150

XLT SuperCrew 4WD

29,935 miles

$41,000

Good Deal
Certified Pre-Owned
Schenectady, NY
46 mi away
Year:
2023
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:
Agate Black Metallic
Combined gas mileage:
23 MPG
Fuel type:
Hybrid
Interior color:
Black
Transmission:
Automatic
Mileage:
29,935
Stock number:
P26300
VIN:
1FTFW1ED3PFD28305

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2021 Chevrolet Silverado 1500

Custom Trail Boss Crew Cab 4WD

44,505 miles

$33,899

Good Deal
Warrensburg, NY
78 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:
Summit White
Combined gas mileage:
15 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
44,505
Stock number:
6848PRA
VIN:
1GCPYCEF6MZ171584

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2023 Ford F-150

XLT SuperCrew 4WD

40,315 miles

$34,500

Great Deal
Amsterdam, NY
66 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:
Stone Gray Metallic
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black W/Medium Dark Slate
Transmission:
Automatic
Mileage:
40,315
Stock number:
U0021
VIN:
1FTFW1E84PFA34639

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2021 Jeep Gladiator

Overland Crew Cab 4WD

37,221 miles

$27,849

Great Deal
Certified Pre-Owned
Natick, MA
88 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:
Sting-Gray Clearcoat
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
37,221
Stock number:
J50508A
VIN:
1C6HJTFG1ML587469

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2023 RAM 1500

Big Horn Crew Cab 4WD

44,727 miles

$33,976

Fair Deal
Certified Pre-Owned
Clifton Park, NY
45 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:
Diamond Black Crystal Pearlcoat
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
44,727
Stock number:
12UPN517700
VIN:
1C6RRFFG2PN517700

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2022 RAM 1500

Classic Warlock Quad Cab 4WD

16,819 miles

$32,900

Fair Deal
Certified Pre-Owned
Granville, NY
61 mi away
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:
16,819
Stock number:
26Z039
VIN:
1C6RR7GG9NS173446

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2022 Chevrolet Silverado 1500

LT Double Cab 4WD

46,201 miles

$31,995

Good Deal
Greenwich, NY
47 mi away
Year:
2022
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
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
46,201
Stock number:
U10792
VIN:
1GCRYDED4NZ188026

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2023 Chevrolet Silverado 1500

Custom Crew Cab 4WD

18,854 miles

$33,900

Good Deal
North Attleboro, MA
95 mi away
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:
Red Hot
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
18,854
Stock number:
23P9905
VIN:
1GCPDBEK9PZ199905

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2023 Jeep Gladiator

Rubicon Crew Cab 4WD

36,527 miles

$36,630

Fair Deal
Certified Pre-Owned
Chicopee, MA
34 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:
36,527
Stock number:
PV26014A
VIN:
1C6JJTBG4PL525530

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