CarGurus Logo Homepage Link
  • Buy
    • Used cars
    • New cars
    • Certified pre-owned
    • Start your purchase online
    • Dealerships near me
  • Sell
    • Sell my car
    • Car values
    • Sell my car FAQs
  • Finance
    • Prequalify for financing
    • How does it work?
    • Financing FAQs
  • Research
    • Test drive reviews
    • Price trends
    • Tips & advice
    • Electric cars
    • Compare cars
  • Discover
    The latest way to shop:
    smarter research, better
    listings.
  • Saved cars & searches
  • Sign in / Register
    • My account
    • Saved searches
    • Saved cars
    • Recommended cars
    • Browsing history
    • Financing dashboard
      • United States (EN)
      • Estados Unidos (ES)
      • Canada (EN)
      • Canada (FR)
      • United Kingdom

Single Cab Pickup Trucks for Sale in Winchester, MA

948 results
Winchester, MA
2015 Chevrolet Silverado 2500HD Work Truck LB 4WD Wayland Automotive

2015 Chevrolet Silverado 2500HD

Work Truck LB 4WD

58,901 miles

$24,950

Fair Deal
Wayland, MA
14 mi away
Year:
2015
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
360 hp 6L V8 Flex Fuel Vehicle
Exterior color:
Victory Red
Fuel type:
Flex Fuel Vehicle
Interior color:
Dark Ash with Jet Black Interior Accents
Transmission:
Automatic
Mileage:
58,901
Stock number:
14422
VIN:
1GC0KUEG3FZ514422

Sponsored

2023 Chevrolet Silverado 1500 Work Truck 4WD

2023 Chevrolet Silverado 1500

Work Truck 4WD

33,172 miles

$28,807

Fair Deal
Haverhill, MA
22 mi away
Year:
2023
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
2 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:
Black
Transmission:
8-Speed Automatic
Mileage:
33,172
Stock number:
265027A
VIN:
3GCNDAEK4PG212576

Sponsored

2023 RAM 1500 Classic Tradesman LB RWD

2023 RAM 1500

Classic Tradesman LB RWD

37,925 miles

$22,498

Fair Deal
Milford, MA
27 mi away
Year:
2023
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
4X2
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:
37,925
Stock number:
P4532
VIN:
3C6JR6DG3PG555008

Sponsored

2022 Chevrolet Silverado 2500HD Work Truck LB 4WD

2022 Chevrolet Silverado 2500HD

Work Truck LB 4WD

40,793 miles

$35,695

Good Deal
Certified Pre-Owned
Salem, NH
22 mi away
Year:
2022
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
401 hp 6.6L V8
Exterior color:
Red Hot
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
40,793
Stock number:
F23631A
VIN:
1GC3YLE79NF118548

2008 Toyota Tacoma Base

2008 Toyota Tacoma

Base

48,020 miles

$12,499

Fair Deal
Northborough, MA
29 mi away
Year:
2008
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
4X2
Engine:
159 hp 2.7L I4
Fuel type:
Gasoline
Transmission:
4-Speed Automatic Overdrive
Mileage:
48,020
Stock number:
482207
VIN:
5TENX22N58Z482207

2016 Ford F-350 Super Duty Chassis XL DRW 4WD

2016 Ford F-350 Super Duty Chassis

XL DRW 4WD

64,506 miles

$19,900

Great Deal
Worcester, MA
38 mi away
Year:
2016
Make:
Ford
Model:
F-350 Super Duty Chassis
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Red
Fuel type:
Flex Fuel Vehicle
Transmission:
6-Speed Automatic
Mileage:
64,506
Stock number:
2914025
VIN:
1FDRF3H60GEC48175

Preparing for a close up...

Photos coming soon

2015 Chevrolet Silverado 2500HD

Work Truck LB 4WD

81,637 miles

$26,994

Fair Deal
Salem, NH
24 mi away
Year:
2015
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
360 hp 6L V8 Flex Fuel Vehicle
Exterior color:
Black
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray
Transmission:
Automatic
Mileage:
81,637
Stock number:
M6685
VIN:
1GC0KUEG5FZ508475

Preparing for a close up...

Photos coming soon

2012 RAM 1500

ST 4WD

122,272 miles

$12,500

Fair Deal
Derry, NH
29 mi away
Year:
2012
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
390 hp 5.7L V8
Exterior color:
Black
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
122,272
Stock number:
16781
VIN:
3C6JD7AT0CG216853

Preparing for a close up...

Photos coming soon

2009 Dodge RAM 2500

ST LB 4WD

87,645 miles

$11,900

Good Deal
Swansea, MA
48 mi away
Year:
2009
Make:
Dodge
Model:
RAM 2500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
383 hp 5.7L V8
Exterior color:
Blue
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic
Mileage:
87,645
VIN:
3D7KS26T89G514838

Preparing for a close up...

Photos coming soon

2014 RAM 1500

Express 4WD

80,734 miles

$16,795

Fair Deal
East Providence, RI
45 mi away
Year:
2014
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5.7L V8
Exterior color:
Flame Red Clearcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Diesel Gray/Black
Transmission:
6-Speed Automatic
Mileage:
80,734
Stock number:
S10102
VIN:
3C6JR7AT5EG102397

Preparing for a close up...

Photos coming soon

2014 RAM 1500

Tradesman 4WD

139,577 miles

$11,595

Good Deal
Salem, MA
14 mi away
Year:
2014
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5.7L V8
Exterior color:
Agriculture Red
Fuel type:
Gasoline
Interior color:
Black/diesel Gray
Transmission:
Automatic
Mileage:
139,577
Stock number:
1078
VIN:
3C6JR7AT6EG281078

Preparing for a close up...

Photos coming soon

2016 Ford F-250 Super Duty

XL LB

16,527 miles

$23,999

Fair Deal
Hudson, MA
22 mi away
Year:
2016
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
4X2
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Ingot Silver Metallic
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray (STEEL CLOTH)
Transmission:
6-Speed Automatic
Mileage:
16,527
Stock number:
H1325
VIN:
1FTBF2A69GEC33426

Preparing for a close up...

Photos coming soon

2016 RAM 1500

Tradesman 4WD

132,413 miles

$9,923

Great Deal
Nashua, NH
24 mi away
Year:
2016
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5.7L V8
Exterior color:
Bright White Clearcoat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
132,413
Stock number:
250260A
VIN:
3C6JR7AT8GG207664

Preparing for a close up...

Photos coming soon

2014 Ford F-350 Super Duty Chassis

XL DRW LB 4WD

111,860 miles

$18,777

Good Deal
Wakefield, MA
5 mi away
Year:
2014
Make:
Ford
Model:
F-350 Super Duty Chassis
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
White
Fuel type:
Flex Fuel Vehicle
Interior color:
Black (Charcoal)
Transmission:
6-Speed Automatic
Mileage:
111,860
VIN:
1FDRF3H68EEB49178

Preparing for a close up...

Photos coming soon

2012 RAM 1500

Express 4WD

79,991 miles

$15,991

Good Deal
Shrewsbury, MA
32 mi away
Year:
2012
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
390 hp 5.7L V8
Exterior color:
Black Clear Coat
Combined gas mileage:
16 MPG
Fuel type:
Gasoline
Interior color:
Dark Slate/Medium Graystone
Transmission:
6-Speed Automatic
Mileage:
79,991
Stock number:
C5478
VIN:
3C6JD7AT9CG280258

Preparing for a close up...

Photos coming soon

2012 Chevrolet Silverado 2500HD

Work Truck LB 4WD

33,899 miles

$19,999

Good Deal
Londonderry, NH
30 mi away
Year:
2012
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
360 hp 6L V8
Exterior color:
Summit White
Fuel type:
Gasoline
Interior color:
Gray (Dark Titanium)
Transmission:
6-Speed Automatic Overdrive
Mileage:
33,899
Stock number:
25029B
VIN:
1GC0KVCG1CZ142700

Preparing for a close up...

Photos coming soon

2013 Chevrolet Silverado 1500

LT 4WD

49,845 miles

$18,990

Fair Deal
Wayland, MA
14 mi away
Year:
2013
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
315 hp 5.3L V8 Flex Fuel Vehicle
Exterior color:
Red (Deep Ruby Metallic)
Combined gas mileage:
18 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Black
Transmission:
Automatic
Mileage:
49,845
Stock number:
162099
VIN:
1GCNKSE00DZ162099

Preparing for a close up...

Photos coming soon

2016 Ford F-250 Super Duty

XL LB 4WD

14,926 miles

$24,995

Great Deal
Manchester, NH
39 mi away
Year:
2016
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Blue Jeans Metallic
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray (Steel)
Transmission:
Automatic
Mileage:
14,926
VIN:
1FTBF2B69GEB01510

Preparing for a close up...

Photos coming soon

2019 Ford F-250 Super Duty

XL LB 4WD

22,622 miles

$32,998

Good Deal
Londonderry, NH
30 mi away
Year:
2019
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Race Red
Fuel type:
Flex Fuel Vehicle
Interior color:
Medium Earth Gray
Transmission:
6-Speed Automatic
Mileage:
22,622
Stock number:
25718A
VIN:
1FTBF2B69KEF66250

Preparing for a close up...

Photos coming soon

2016 Ford F-350 Super Duty

XLT LB 4WD

36,890 miles

$22,577

Great Deal
Wakefield, MA
5 mi away
Year:
2016
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
316 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Oxford White
Fuel type:
Flex Fuel Vehicle
Interior color:
Steel Gray
Transmission:
6-Speed Automatic
Mileage:
36,890
VIN:
1FTBF3B63GEA51192

Preparing for a close up...

Photos coming soon

2018 Ford F-250 Super Duty

XL LB 4WD

87,294 miles

$31,994

Fair Deal
Salem, NH
24 mi away
Year:
2018
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Gray
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray
Transmission:
Automatic
Mileage:
87,294
Stock number:
M6697
VIN:
1FTBF2B64JEC72981

Preparing for a close up...

Photos coming soon

2010 Toyota Tacoma

Regular Cab 4WD

143,447 miles

$13,587

Fair Deal
Manchester, NH
38 mi away
Year:
2010
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
159 hp 2.7L I4
Exterior color:
Black Sand Pearl
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
5-Speed Manual
Mileage:
143,447
Stock number:
AZ734293
VIN:
5TEPX4EN6AZ734293

Preparing for a close up...

Photos coming soon

2017 Ford F-250 Super Duty

XL LB 4WD

76,273 miles

$22,950

Great Deal
East Brookfield, MA
50 mi away
Year:
2017
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Ingot Silver (ux)
Fuel type:
Flex Fuel Vehicle
Interior color:
Medium Earth Gray (4s)
Transmission:
6-Speed Automatic
Mileage:
76,273
Stock number:
HEE90084
VIN:
1FTBF2B69HEE90084

Preparing for a close up...

Photos coming soon

2016 Ford F-350 Super Duty

XLT LB 4WD

36,890 miles

$22,577

Great Deal
Wakefield, MA
5 mi away
Year:
2016
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Four-Wheel Drive
Engine:
316 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Oxford White
Fuel type:
Flex Fuel Vehicle
Interior color:
Steel Gray
Transmission:
6-Speed Automatic
Mileage:
36,890
VIN:
1FTBF3B63GEA51192

Sponsored

  • Toyota Trucks for Sale in Winchester MA

  • Classic Trucks for Sale in Winchester MA

  • Manual Transmission Trucks for Sale in Winchester MA

  • OBS (1987 - 1997) Ford Trucks for Sale in Winchester MA

  • 1980s-era Trucks for Sale in Winchester MA

  • Manual Diesel Trucks for Sale in Winchester MA

  • Used Electric Pickup Trucks for Sale

  • Single Cab Pickup Trucks for Sale in Boston MA

  • Single Cab Pickup Trucks for Sale in Groton MA

  • Single Cab Pickup Trucks for Sale in Worcester MA

  • Single Cab Pickup Trucks for Sale in Manchester NH

  • Single Cab Pickup Trucks for Sale in Plymouth MA

  • Single Cab Pickup Trucks for Sale in Providence RI

  • Single Cab Pickup Trucks for Sale in Portsmouth NH

  • Single Cab Pickup Trucks for Sale in New Bedford MA

  • Single Cab Pickup Trucks for Sale in Chicopee MA

  • All Used Cars

  • Manual Transmission Cars

  • Luxury Cars

  • Cars with Red Interior

  • Cheap Manual Cars

  • Hybrid Cars

  • Sports Cars

  • Electric SUVs

  • Cheap Trucks

  • Small Cars

  • Third Row SUVs

  • Three Quarter Ton Trucks

  • Lifted Trucks

  • Manual Transmission Trucks

  • Diesel Trucks

  • Hybrid SUVs

  • Dually Trucks

  • One Ton Trucks

  • Cheap SUVs

  • Lifted Ford Trucks

  • 4x4 Trucks

  • Work Trucks

  • AWD SUVs

  • Ford Trucks

  • Chevrolet Trucks

  • Toyota Trucks

  • Trucks Under $10,000

  • Cars Under $15,000

  • Sports Cars Under $20,000

  • Trucks Under $20,000

  • Used Sedans for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • Used Hatchbacks for Sale with Low Mileage

  • Used Convertibles for Sale with Low Mileage

  • Used Vans for Sale with Low Mileage

  • Used Minivans for Sale with Low Mileage

  • Used Pickup Trucks for Sale with Low Mileage

  • Used Coupes for Sale with Low Mileage

  • Used Wagons for Sale with Low Mileage

  • Bourne's Auto Center

  • The Highline Group

  • Avon Auto Brokers

  • Maserati Alfa Romeo Motorsports of Boston

  • Midway Automotive

  • Autobahn USA - Dedham

  • ShopiCar

  • BidCars Boston

  • Lexus of Watertown

  • Toyota of Nashua

  • Herb Chambers BMW of Sudbury

  • Webster Auto Sales

Connect with us
Download our app
Download on the App Store Get it on Google Play
  • Company
  • About CarGurus
  • Our team
  • Press
  • Investor relations
  • Price trends
  • Careers
  • Advertise with CarGurus
  • For dealers
  • Dealer signup
  • Dealer resources
  • Terms
  • Terms of use
  • Privacy policy
  • Interest-based ads
  • Security
  • Help
  • Help center
  • Contact us
Click for the BBB Business Review of this Auto Listing Service in Cambridge MA
    • United States (EN)
    • Estados Unidos (ES)
    • Canada (EN)
    • Canada (FR)
    • United Kingdom

© 2026 CarGurus, Inc., All Rights Reserved.