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Best Pickup Trucks For Sale in Winsted, CT

1,161 results
Winsted, CT
2023 GMC Sierra 1500 Denali Ultimate Crew Cab 4WD Blasius Mitsubishi

2023 GMC Sierra 1500

Denali Ultimate Crew Cab 4WD

36,786 miles

$56,689

Good Deal
Brookfield, CT
38 mi away
Year:
2023
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:
17 MPG
Fuel type:
Gasoline
Interior color:
Alpine Umber
Transmission:
Automatic
Mileage:
36,786
Stock number:
Z4157
VIN:
1GTUUHEL2PZ291937

Sponsored

2022 Ford F-150 XLT SuperCrew 4WD

2022 Ford F-150

XLT SuperCrew 4WD

27,681 miles

$40,891

Good Deal
Certified Pre-Owned
Glastonbury, CT
31 mi away
Year:
2022
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 5L V8 Flex Fuel Vehicle
Exterior color:
Iconic Silver Metallic
Combined gas mileage:
19 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
27,681
Stock number:
22UC8799
VIN:
1FTFW1E50NKE44963

Sponsored

2021 RAM 1500 Laramie Crew Cab 4WD

2021 RAM 1500

Laramie Crew Cab 4WD

55,298 miles

$34,990

Good Deal
Vernon Rockville, CT
32 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:
55,298
Stock number:
P15565
VIN:
1C6SRFJT6MN591011

Sponsored

2021 GMC Sierra 1500 Denali Crew Cab 4WD

2021 GMC Sierra 1500

Denali Crew Cab 4WD

49,307 miles

$39,900

Good Deal
Poughkeepsie, NY
48 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:
Black (Ebony Twilight Metallic)
Combined gas mileage:
24 MPG
Fuel type:
Diesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
49,307
Stock number:
31867
VIN:
3GTU9FET2MG337736

2023 Ford F-250 Super Duty Lariat Crew Cab 4WD

2023 Ford F-250 Super Duty

Lariat Crew Cab 4WD

63,605 miles

$49,800

Great Deal
Kingston, NY
49 mi away
Year:
2023
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
430 hp 7.3L V8
Exterior color:
Blue Metallic
Fuel type:
Gasoline
Interior color:
Black Onyx
Transmission:
Automatic
Mileage:
63,605
Stock number:
KJ24662A
VIN:
1FT8W2BN7PEC18438

2023 Ford Maverick XLT SuperCrew AWD

2023 Ford Maverick

XLT SuperCrew AWD

45,677 miles

$23,466

Great Deal
New Britain, CT
27 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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2021 GMC Sierra 1500

Denali Crew Cab 4WD

82,694 miles

$35,000

Great Deal
Certified Pre-Owned
Springfield, MA
28 mi away
Year:
2021
Make:
GMC
Model:
Sierra 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
420 hp 6.2L V8
Exterior color:
White Frost Tricoat
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Gray (Dark Walnut/Dark Ash Grey)
Transmission:
Automatic
Mileage:
82,694
Stock number:
JG2742ZA
VIN:
3GTU9FELXMG354784

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2021 RAM 1500

Big Horn Crew Cab 4WD

44,493 miles

$32,746

Fair Deal
Certified Pre-Owned
Holyoke, MA
28 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 Clearcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
44,493
Stock number:
A7609A
VIN:
1C6SRFFT9MN521009

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2022 Ford F-150

King Ranch SuperCrew 4WD

53,460 miles

$44,385

Great Deal
Willimantic, CT
47 mi away
Year:
2022
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 5L V8 Flex Fuel Vehicle
Exterior color:
Brown
Combined gas mileage:
19 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Java
Transmission:
Automatic
Mileage:
53,460
Stock number:
210530A
VIN:
1FTFW1E52NFB93582

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2021 Jeep Gladiator

Rubicon Crew Cab 4WD

38,996 miles

$31,000

Great Deal
Certified Pre-Owned
East Hartford, CT
26 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:
6-Speed Manual
Mileage:
38,996
Stock number:
19521Q
VIN:
1C6JJTBG3ML501716

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2022 Chevrolet Silverado 1500

RST Crew Cab 4WD

7,586 miles

$44,987

Fair Deal
Vernon Rockville, CT
32 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:
Summit White
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
7,586
Stock number:
10764
VIN:
2GCUDEED4N1500771

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2021 RAM 1500

Laramie Crew Cab 4WD

56,758 miles

$35,248

Good Deal
Watertown, CT
25 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:
Bright White Clearcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
56,758
Stock number:
RAM70286A
VIN:
1C6SRFJT7MN810591

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2022 GMC Canyon

AT4 Crew Cab 4WD with Cloth

38,517 miles

$28,900

Great Deal
Pittsfield, MA
35 mi away
Year:
2022
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:
20 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Kalahari
Transmission:
8-Speed Automatic
Mileage:
38,517
Stock number:
HHA2131
VIN:
1GTG6FEN5N1157500

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2022 RAM 1500

Laramie Crew Cab 4WD

67,693 miles

$33,995

Great Deal
Willimantic, CT
47 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:
67,693
Stock number:
12171T
VIN:
1C6SRFJT2NN378610

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2021 RAM 1500

Big Horn Quad Cab 4WD

45,934 miles

$31,596

Fair Deal
Hudson, NY
39 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:
45,934
Stock number:
2198P
VIN:
1C6SRFBT4MN623341

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2023 Chevrolet Colorado

LT Crew Cab 4WD

21,189 miles

$33,459

Great Deal
Lake Katrine, NY
46 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:
Harvest Bronze Metallic
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
21,189
Stock number:
26103A
VIN:
1GCPTCEK9P1152347

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2023 RAM 1500

Laramie Crew Cab 4WD

41,168 miles

$36,710

Great Deal
Branford, CT
49 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:
Gray (Granite Crystal Metallic Clearcoat)
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
41,168
Stock number:
11573
VIN:
1C6SRFJT2PN672639

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2023 Chevrolet Silverado 1500

LT Crew Cab 4WD

52,037 miles

$31,080

Great Deal
Watertown, CT
27 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:
Summit White
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
52,037
Stock number:
K3023
VIN:
3GCUDDED3PG346087

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2021 Chevrolet Silverado 1500

Custom Crew Cab 4WD

69,130 miles

$25,120

Great Deal
Watertown, CT
27 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:
Summit White
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
69,130
Stock number:
K2975
VIN:
1GCPYBEK1MZ323651

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2023 Toyota Tacoma

TRD Off Road Double Cab 4WD

23,793 miles

$38,799

Good Deal
Danbury, CT
41 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
Transmission:
6-Speed Automatic
Mileage:
23,793
Stock number:
BH30
VIN:
3TYCZ5AN1PT132982

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2022 Chevrolet Silverado 1500

LT Crew Cab 4WD

26,007 miles

$31,988

Great Deal
Torrington, CT
10 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:
Black
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
26,007
Stock number:
N5275
VIN:
1GCPDKEKXNZ561060

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2023 Chevrolet Silverado 1500

High Country Crew Cab 4WD

20,032 miles

$49,984

Good Deal
Vernon Rockville, CT
32 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 Ford F-150

XLT SuperCrew 4WD

30,276 miles

$39,488

Good Deal
Certified Pre-Owned
Watertown, CT
27 mi away
Year:
2022
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
400 hp 5L V8 Flex Fuel Vehicle
Exterior color:
Black
Combined gas mileage:
19 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray
Transmission:
Automatic
Mileage:
30,276
Stock number:
U74525
VIN:
1FTFW1E59NFA74525

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2021 Jeep Gladiator

Sport Crew Cab 4WD

25,555 miles

$31,488

Fair Deal
Certified Pre-Owned
Ellington, CT
33 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:
Hydro Blue Pearlcoat
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
25,555
Stock number:
904728
VIN:
1C6HJTAG1ML622342

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