Best Pickup Trucks For Sale inWinchester Center, CT
1,113 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Blue
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 70,092
- Stock #:
- HQ454
- VIN:
- 1GCRYJEK3MZ310466
Sponsored by Danbury Auto Group
2021 Chevrolet Silverado 1500
LT Double Cab 4WD
70,092 mi
Danbury, CT
37 mi away
Great Deal
$24,005
- 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:
- Black
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 31,313
- Stock #:
- FS26323
- VIN:
- 1FTEW1EP3PKD98867
Price drop
-$2,000
Sponsored Listing
2023 Ford F-150
XL SuperCrew 4WD
31,313 mi
Lake Katrine, NY
43 mi away
Great Deal
$36,174
$34,174
- 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:
- Black Onyx/Dark Slat
- Transmission:
- Automatic
- Mileage:
- 120,396
- Stock #:
- A06561
- VIN:
- 3FTTW8F93NRA06561
New arrival
Sponsored Listing
2022 Ford Maverick
XLT SuperCrew AWD
120,396 mi
Waterbury, CT
22 mi away
Fair Deal
$19,694
- 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:
- Delmonico Red Pearlcoat
- Fuel type:
- Gasoline
- Interior color:
- Diesel Gray/Black
- Mileage:
- 49,024
- Stock #:
- 5546A
- VIN:
- 1C6SRFFT4NN374597
Price drop
-$820
2022 RAM 1500
Big Horn Crew Cab 4WD
49,024 mi
West Springfield, MA
30 mi away
Great Deal
$35,690
$34,870
- 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:
- Automatic
- Mileage:
- 15,689
- Stock #:
- 31176
- VIN:
- 1GTRUJEK4PZ293080
2023 GMC Sierra 1500
Elevation Standard Double Cab 4WD
15,689 mi
West Springfield, MA
30 mi away
Fair Deal
$41,190
- 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:
- 73,565
- Stock #:
- U1948
- VIN:
- 1C6SRFDT4MN714851
2021 RAM 1500
Laramie Quad Cab 4WD
73,565 mi
Milford, CT
48 mi away
Great Deal
$28,939
- 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:
- Black Clearcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 42,352
- Stock #:
- 20000MA4
- VIN:
- 1C6HJTAG1NL143243
2022 Jeep Gladiator
Willys Crew Cab 4WD
42,352 mi
North Haven, CT
37 mi away
Good Deal
$29,333
- 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:
- Snazzberry Pearlcoat
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 44,607
- Stock #:
- T26147A
- VIN:
- 1C6JJTBG5ML566888
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
44,607 mi
Catskill, NY
44 mi away
Fair Deal
$35,475
- 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:
- Northsky Blue Metallic
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 19,123
- Stock #:
- V16409A
- VIN:
- 1GCUYEED6MZ348227
2021 Chevrolet Silverado 1500
RST Crew Cab 4WD
19,123 mi
Palmer, MA
46 mi away
Good Deal
$40,771
- 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:
- Gray (Satin Steel Metallic)
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 41,301
- Stock #:
- 11951
- VIN:
- 1GTG6EENXN1100753
2022 GMC Canyon
Denali Crew Cab 4WD
41,301 mi
Branford, CT
46 mi away
Great Deal
$33,987
- 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:
- [PXJ] Diamond Black Crystal Pearl Coat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,152
- Stock #:
- 7996
- VIN:
- 1C6SRFHT7NN455784
![[PXJ] Diamond Black Crystal Pearl Coat 2022 RAM 1500 Pickup Truck Four-Wheel Drive Automatic](https://static.cargurus.com/images/forsale/2026/07/15/17/05/2022_ram_1500-pic-3305366243596089158-1024x768.jpeg?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
2022 RAM 1500
Limited Crew Cab 4WD
52,152 mi
Branford, CT
46 mi away
Good Deal
$43,493
- 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:
- 58,032
- Stock #:
- P10198
- VIN:
- 1C6SRFLT1PN588096
2023 RAM 1500
Rebel Crew Cab 4WD
58,032 mi
West Springfield, MA
30 mi away
Fair Deal
$44,879
- 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:
- [PAU] Granite Crystal Metallic Clear Coat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 63,181
- Stock #:
- 7969
- VIN:
- 1C6SRFHT7NN448818
![[PAU] Granite Crystal Metallic Clear Coat 2022 RAM 1500 Pickup Truck Four-Wheel Drive Automatic](https://static.cargurus.com/images/forsale/2026/07/02/14/08/2022_ram_1500-pic-4614673432782724023-1024x768.jpeg?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
2022 RAM 1500
Limited Crew Cab 4WD
63,181 mi
Branford, CT
46 mi away
Fair Deal
$42,493
- 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:
- 57,881
- Stock #:
- 20143MK2
- VIN:
- 1C6SRFJT8MN679574
2021 RAM 1500
Laramie Crew Cab 4WD
57,881 mi
North Haven, CT
37 mi away
Fair Deal
$35,879
- 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:
- 36,715
- Stock #:
- NAV06469C
- VIN:
- 1C6SRFBT0MN517243
2021 RAM 1500
Big Horn Quad Cab 4WD
36,715 mi
Watertown, CT
23 mi away
Good Deal
$32,299
- 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:
- Billet Silver Metallic Clearcoat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 61,338
- Stock #:
- 11982
- VIN:
- 1C6SRFJT4PN660590
New arrival
2023 RAM 1500
Laramie Crew Cab 4WD
61,338 mi
Branford, CT
46 mi away
Good Deal
$37,849
- 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:
- Blue
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 18,425
- Stock #:
- J9504A
- VIN:
- 1C6SRFHT5NN330489
2022 RAM 1500
Limited Crew Cab 4WD
18,425 mi
Colchester, CT
48 mi away
Fair Deal
$50,799
- 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:
- Silver Ice Metallic
- Combined gas mileage:
- 20 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,383
- Stock #:
- 9458
- VIN:
- 1GCPYJEK8MZ444185
2021 Chevrolet Silverado 1500
LT Crew Cab 4WD
22,383 mi
Terryville, CT
16 mi away
Fair Deal
$33,721
- 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:
- 56,769
- Stock #:
- Z4705
- VIN:
- 1C6RRFFGXPN521767
2023 RAM 1500
Big Horn Crew Cab 4WD
56,769 mi
Brookfield, CT
34 mi away
Great Deal
$31,986
- Year:
- 2023
- Make:
- Ford
- Model:
- Maverick
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 250 hp 2L I4
- Exterior color:
- Carbonized Gray Metallic
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black Onyx
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,400
- Stock #:
- U28467
- VIN:
- 3FTTW8F99PRB03704
2023 Ford Maverick
Lariat SuperCrew AWD
11,400 mi
Litchfield, CT
12 mi away
Fair Deal
$32,589
- Year:
- 2021
- Make:
- Jeep
- Model:
- Gladiator
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 260 hp 3L V6 Diesel
- Exterior color:
- Gray (Granite Crystal Metallic Clearcoat)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 87,848
- Stock #:
- HUP1412
- VIN:
- 1C6JJTBM5ML503568
2021 Jeep Gladiator
Rubicon Crew Cab 4WD
87,848 mi
Fishkill, NY
48 mi away
Great Deal
$28,575
- Year:
- 2022
- Make:
- GMC
- Model:
- Sierra 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 277 hp 3L I6 Diesel
- Exterior color:
- Pacific Blue Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Diesel
- Interior color:
- Alpine Umber
- Transmission:
- Automatic
- Mileage:
- 64,418
- Stock #:
- 326951A
- VIN:
- 1GTUUHET4NZ515965
2022 GMC Sierra 1500
Denali Ultimate Crew Cab 4WD
64,418 mi
Branford, CT
46 mi away
Good Deal
$48,987
- 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:
- [PAU] Granite Crystal Metallic Clear Coat
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 66,856
- Stock #:
- 7911
- VIN:
- 1C6SRFMT9NN417995
![[PAU] Granite Crystal Metallic Clear Coat 2022 RAM 1500 Pickup Truck Four-Wheel Drive Automatic](https://static.cargurus.com/images/forsale/2026/06/18/16/54/2022_ram_1500-pic-7684123915964393651-1024x768.jpeg?io=true&width=640&height=480&fit=bounds&format=jpg&auto=webp)
Price drop
-$1,000
2022 RAM 1500
Big Horn Crew Cab 4WD
66,856 mi
Branford, CT
46 mi away
Good Deal
$33,993
$32,993
- 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/Red
- Transmission:
- 6-Speed Automatic
- Mileage:
- 28,589
- Stock #:
- PT153791TL
- VIN:
- 3TYCZ5AN0PT153791
Sponsored Listing
2023 Toyota Tacoma
SR5 V6 Double Cab 4WD
28,589 mi
Wilbraham, MA
38 mi away
Good Deal
$37,428
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