Best Pickup Trucks For Sale inWindsor, MA
3,522 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Summit White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 51,496
- Stock #:
- M5024
- VIN:
- 1GCRDDED5PZ331371
Sponsored by Ruge's Automotive
2023 Chevrolet Silverado 1500
LT Double Cab 4WD
51,496 mi
Rhinebeck, NY
58 mi away
Good Deal
$34,544
- 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:
- Dark Ash Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,078
- Stock #:
- 4U00118
- VIN:
- 3GCPDKEK8PG254831
Sponsored Listing
2023 Chevrolet Silverado 1500
LT Crew Cab 4WD
36,078 mi
Johnston, RI
92 mi away
Fair Deal
$33,518
- Year:
- 2022
- Make:
- Toyota
- Model:
- Tacoma
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- 4X2
- Engine:
- 159 hp 2.7L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic
- Mileage:
- 24,596
- Stock #:
- 515732
- VIN:
- 3TYRX5GN9NT052060
Sponsored Listing
2022 Toyota Tacoma
SR5 I4 Access Cab RWD
24,596 mi
Northampton, MA
24 mi away
Good Deal
$29,188
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cement/Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 87,851
- Stock #:
- CP3158
- VIN:
- 3TMCZ5AN7NM499099
2022 Toyota Tacoma
TRD Off Road Double Cab 4WD
87,851 mi
Old Saybrook, CT
90 mi away
Good Deal
$32,769
- Year:
- 2022
- Make:
- RAM
- Model:
- 2500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 370 hp 6.7L I6 Diesel
- Exterior color:
- Pearl White
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 40,786
- Stock #:
- BUK4891
- VIN:
- 3C6UR5PL2NG360546
New arrival
2022 RAM 2500
Limited Longhorn Mega Cab 4WD
40,786 mi
Poughkeepsie, NY
76 mi away
Fair Deal
$63,165
- 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
65 mi away
Good Deal
$26,395
- 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:
- Iconic Silver
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black w/Medium Dark Slate
- Transmission:
- Automatic
- Mileage:
- 16,693
- Stock #:
- U28424
- VIN:
- 1FTEW1EP5NFB89717
Price drop
-$1,000
2022 Ford F-150
XL SuperCrew 4WD
16,693 mi
Litchfield, CT
54 mi away
Great Deal
$34,589
$33,589
- 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:
- Ivory White Tri-Coat Pearlcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Mountain Brown
- Transmission:
- 8-Speed Automatic
- Mileage:
- 46,057
- Stock #:
- 7166P
- VIN:
- 1C6SRFKT6MN608033
2021 RAM 1500
Limited Longhorn Crew Cab 4WD
46,057 mi
Warrensburg, NY
78 mi away
Good Deal
$40,302
- 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 Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 67,046
- Stock #:
- HN0677A
- VIN:
- 1C6SRFFT0MN669176
2021 RAM 1500
Big Horn Crew Cab 4WD
67,046 mi
Northampton, MA
24 mi away
Great Deal
$28,975
- Year:
- 2021
- Make:
- GMC
- Model:
- Canyon
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 308 hp 3.6L V6
- Exterior color:
- Onyx Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,298
- Stock #:
- U28634
- VIN:
- 1GTG6EEN1M1128634
Price drop
-$2,712
2021 GMC Canyon
Denali Crew Cab 4WD
52,298 mi
Watertown, CT
65 mi away
Great Deal
$30,499
$27,787
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Colorado
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 308 hp 3.6L V6
- Exterior color:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black/Dark Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 25,549
- Stock #:
- H14322Y
- VIN:
- 1GCGTBEN7N1109739
2022 Chevrolet Colorado
Work Truck Crew Cab 4WD
25,549 mi
White River Junction, VT
86 mi away
Great Deal
$26,757
- 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:
- 93,410
- Stock #:
- ELA49867A
- VIN:
- 1GCPYFED7MZ191021
Price drop
-$2,450
2021 Chevrolet Silverado 1500
LT Trail Boss Crew Cab 4WD
93,410 mi
Watertown, CT
65 mi away
Great Deal
$31,049
$28,599
- 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:
- Crystal Metallic
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,639
- Stock #:
- 5AP5105
- VIN:
- 1C6HJTAG4ML535681
2021 Jeep Gladiator
Sport Crew Cab 4WD
43,639 mi
Albany, NY
39 mi away
Great Deal
$25,750
- Year:
- 2022
- Make:
- Ford
- Model:
- Maverick
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 250 hp 2L I4
- Exterior color:
- Area 51
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Desert Brown
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,267
- Stock #:
- FEU8368A
- VIN:
- 3FTTW8F95NRA90351
2022 Ford Maverick
Lariat SuperCrew AWD
60,267 mi
Poughkeepsie, NY
75 mi away
Fair Deal
$26,169
- 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:
- 20,776
- Stock #:
- AC9350
- VIN:
- 1GCRDKEKXPZ277553
Price drop
-$1,500
2023 Chevrolet Silverado 1500
LT Double Cab 4WD
20,776 mi
Old Saybrook, CT
90 mi away
Good Deal
$35,025
$33,525
- 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
100 mi away
Fair Deal
$31,461
- 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:
- Black Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 68,654
- Stock #:
- K3319
- VIN:
- 1FTEW1EP5NFA63597
New arrival
2022 Ford F-150
XL SuperCrew 4WD
68,654 mi
Watertown, CT
65 mi away
Great Deal
$27,988
- 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:
- Summit White
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 74,563
- Stock #:
- TC1628A
- VIN:
- 3GTPUJEK0PG227102
2023 GMC Sierra 1500
Elevation Standard Crew Cab 4WD
74,563 mi
Bow, NH
90 mi away
Great Deal
$27,900
- Year:
- 2023
- Make:
- Nissan
- Model:
- Frontier
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 3.8L V6
- Exterior color:
- Glacier White
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Steel)
- Transmission:
- 9-Speed Automatic
- Mileage:
- 46,068
- Stock #:
- SC308867A
- VIN:
- 1N6ED1EK9PN666830
2023 Nissan Frontier
PRO-4X Crew Cab 4WD
46,068 mi
Danbury, CT
82 mi away
Fair Deal
$33,499
- 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:
- Army Green
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 70,777
- Stock #:
- JE346
- VIN:
- 3TMCZ5ANXMM378842
New arrival
2021 Toyota Tacoma
TRD Off Road Double Cab 4WD
70,777 mi
Branford, CT
86 mi away
Good Deal
$34,094
- 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:
- 40,924
- Stock #:
- U28508
- VIN:
- 1C6HJTAGXPL553543
Price drop
-$1,000
2023 Jeep Gladiator
Willys Crew Cab 4WD
40,924 mi
Litchfield, CT
54 mi away
Good Deal
$32,589
$31,589
- Year:
- 2022
- Make:
- RAM
- Model:
- 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Bright White Clear Coat
- Interior color:
- Black (Charcoal)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,790
- Stock #:
- 5526
- VIN:
- 1C6RRFFG3NN248765
New arrival
2022 RAM 1500
Big Horn Crew Cab 4WD
49,790 mi
Feeding Hills, MA
36 mi away
Great Deal
$30,394
- 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
95 mi away
Fair Deal
$32,407
$31,399
- 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
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 21,405
- Stock #:
- BU2554A
- VIN:
- 3GCUDCED7PG364215
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
21,405 mi
Poughkeepsie, NY
76 mi away
Fair Deal
$42,975
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