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

Used Pickup Trucks for Sale near Windermere, FL

4,607 results
Windermere, FL
2021 Chevrolet Colorado Work Truck Crew Cab RWD AutoNation Chevrolet Airport

2021 Chevrolet Colorado

Work Truck Crew Cab RWD

99,482 miles

$17,645

Fair Deal
Orlando, FL
15 mi away
Year:
2021
Make:
Chevrolet
Model:
Colorado
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
200 hp 2.5L I4
Exterior color:
Cherry Red Tintcoat
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Jet Black/Dark Ash
Transmission:
6-Speed Automatic
Mileage:
99,482
Stock number:
M1268039
VIN:
1GCGSBEA8M1268039

Sponsored

2020 Ford F-250 Super Duty King Ranch Crew Cab 4WD

2020 Ford F-250 Super Duty

King Ranch Crew Cab 4WD

181,204 miles

$43,500

Fair Deal
Apopka, FL
14 mi away
Year:
2020
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.7L V8 Biodiesel
Exterior color:
Agate Black Metallic
Fuel type:
Biodiesel
Interior color:
Java
Transmission:
Automatic
Mileage:
181,204
Stock number:
E66389
VIN:
1FT7W2BT4LEE66389

Sponsored

2019 GMC Sierra 1500 AT4 Crew Cab 4WD

2019 GMC Sierra 1500

AT4 Crew Cab 4WD

132,320 miles

$28,302

Fair Deal
Mount Dora, FL
25 mi away
Year:
2019
Make:
GMC
Model:
Sierra 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Pacific Blue Metallic
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Jet Black
Transmission:
8-Speed Automatic
Mileage:
132,320
Stock number:
209430B
VIN:
1GTP9EED2KZ406132

Sponsored

2021 Chevrolet Silverado 3500HD Work Truck Crew Cab LB 4WD

2021 Chevrolet Silverado 3500HD

Work Truck Crew Cab LB 4WD

134,045 miles

$32,015

Good Deal
Bartow, FL
44 mi away
Year:
2021
Make:
Chevrolet
Model:
Silverado 3500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.6L V8 Biodiesel
Exterior color:
Summit White
Fuel type:
Biodiesel
Interior color:
Jet Black
Transmission:
Automatic
Mileage:
134,045
Stock number:
MF241418
VIN:
1GB4YSEY5MF241418

2016 Toyota Tacoma Double Cab V6 SR5

2016 Toyota Tacoma

Double Cab V6 SR5

115,870 miles

$19,000

Good Deal
Titusville, FL
46 mi away
Year:
2016
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
278 hp 3.5L V6
Exterior color:
White
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
6-Speed Automatic
Mileage:
115,870
Stock number:
SC338068A
VIN:
3TMAZ5CN4GM007474

2023 Hyundai Santa Cruz Limited Crew Cab AWD

2023 Hyundai Santa Cruz

Limited Crew Cab AWD

23,510 miles

$26,409

Good Deal
Certified Pre-Owned
Leesburg, FL
31 mi away
Year:
2023
Make:
Hyundai
Model:
Santa Cruz
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
281 hp 2.5L I4
Exterior color:
California Sand
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
23,510
Stock number:
L37581A
VIN:
5NTJEDAF3PH074236

Preparing for a close up...

Photos coming soon

2004 Ford F-250 Super Duty

XLT Crew Cab RWD

220,143 miles

$7,990

Fair Deal
Leesburg, FL
31 mi away
Year:
2004
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Rear-Wheel Drive
Engine:
6L V8 Diesel
Exterior color:
White
Fuel type:
Diesel
Interior color:
Gray
Transmission:
5-Speed Automatic Overdrive
Mileage:
220,143
Stock number:
C55387
VIN:
1FTNW20PX4EC55387

Preparing for a close up...

Photos coming soon

2018 RAM 2500

Laramie Crew Cab 4WD

161,655 miles

$20,465

Good Deal
Mount Dora, FL
25 mi away
Year:
2018
Make:
RAM
Model:
2500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
410 hp 6.4L V8
Exterior color:
Bright White Clearcoat
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
161,655
Stock number:
112693A
VIN:
3C6UR5FJ5JG321198

Preparing for a close up...

Photos coming soon

2017 Toyota Tacoma

TRD Sport V6 Double Cab RWD

128,282 miles

$19,868

Good Deal
Orlando, FL
9 mi away
Year:
2017
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
278 hp 3.5L V6
Exterior color:
Super White
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
6-Speed Automatic
Mileage:
128,282
Stock number:
HX023585
VIN:
5TFAZ5CN0HX023585

Preparing for a close up...

Photos coming soon

2015 Ford F-250 Super Duty

XL SuperCab LB

166,523 miles

$12,984

Good Deal
Bartow, FL
44 mi away
Year:
2015
Make:
Ford
Model:
F-250 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
385 hp 6.2L V8 Flex Fuel Vehicle
Exterior color:
Oxford White
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray (Steel)
Transmission:
6-Speed Automatic
Mileage:
166,523
Stock number:
FED50053
VIN:
1FD7X2A64FED50053

Preparing for a close up...

Photos coming soon

2017 Ford F-350 Super Duty

Lariat Crew Cab 4WD

164,607 miles

$34,988

Great Deal
Lakeland, FL
38 mi away
Year:
2017
Make:
Ford
Model:
F-350 Super Duty
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
6.7L V8 Biodiesel
Exterior color:
Blue Jeans
Fuel type:
Biodiesel
Interior color:
Black
Transmission:
6-Speed Automatic
Mileage:
164,607
Stock number:
HEC49749
VIN:
1FT8W3BT6HEC49749

Preparing for a close up...

Photos coming soon

2024 RAM 1500

Classic SLT Quad Cab RWD

61,603 miles

$20,990

Great Deal
Leesburg, FL
29 mi away
Year:
2024
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
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:
61,603
Stock number:
1121PR0038
VIN:
1C6RR6GG9RS137272

Preparing for a close up...

Photos coming soon

2020 RAM 1500

Laramie Crew Cab 4WD

92,632 miles

$26,999

Great Deal
Saint Cloud, FL
24 mi away
Year:
2020
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5.7L V8
Exterior color:
Hydro Blue Pearlcoat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
92,632
Stock number:
275651T
VIN:
1C6SRFJT9LN275651

Preparing for a close up...

Photos coming soon

2006 GMC Canyon

SL 2WD

102,543 miles

$9,248

Fair Deal
Fruitland Park, FL
35 mi away
Year:
2006
Make:
GMC
Model:
Canyon
Body type:
Pickup Truck
Doors:
2 doors
Drivetrain:
Rear-Wheel Drive
Engine:
175 hp 2.8L I4
Exterior color:
Silver Birch Metallic
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Pewter Cloth
Transmission:
4-Speed Automatic
Mileage:
102,543
Stock number:
U413C
VIN:
1GTCS148168210789

Preparing for a close up...

Photos coming soon

2018 Toyota Tundra

SR5 CrewMax 4.6L

42,232 miles

$29,788

Good Deal
Leesburg, FL
28 mi away
Year:
2018
Make:
Toyota
Model:
Tundra
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
310 hp 4.6L V8
Exterior color:
Midnight Black Metallic
Fuel type:
Gasoline
Interior color:
Black
Transmission:
6-Speed Automatic Overdrive
Mileage:
42,232
Stock number:
8P1281A
VIN:
5TFEM5F13JX132850

Preparing for a close up...

Photos coming soon

2024 Chevrolet Silverado 1500

Work Truck Crew Cab RWD

102,710 miles

$20,550

Great Deal
Sanford, FL
24 mi away
Year:
2024
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
355 hp 5.3L V8
Exterior color:
White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
102,710
Stock number:
103047
VIN:
3GCPAAED5RG103047

Preparing for a close up...

Photos coming soon

2019 RAM 1500

Classic Tradesman Crew Cab RWD

138,497 miles

$14,200

Good Deal
Orlando, FL
28 mi away
Year:
2019
Make:
RAM
Model:
1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
395 hp 5.7L V8
Exterior color:
Bright Silver Metallic Clear Coat
Combined gas mileage:
18 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
138,497
Stock number:
642756
VIN:
1C6RR6KT0KS642756

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 1500

LT Trail Boss Crew Cab 4WD

92,019 miles

$28,086

Great Deal
Titusville, FL
46 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 1500
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
355 hp 5.3L V8
Exterior color:
Red Hot
Combined gas mileage:
17 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
92,019
Stock number:
198874T
VIN:
1GCPYFED0KZ198874

Preparing for a close up...

Photos coming soon

2017 Toyota Tacoma

SR5 V6 Double Cab RWD

129,518 miles

$17,687

Great Deal
Winter Haven, FL
35 mi away
Year:
2017
Make:
Toyota
Model:
Tacoma
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
278 hp 3.5L V6
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
129,518
Stock number:
HX045467
VIN:
5TFAZ5CN5HX045467

Preparing for a close up...

Photos coming soon

2018 Ford F-150

XLT SuperCrew 4WD

131,141 miles

$18,978

Good Deal
Fruitland Park, FL
35 mi away
Year:
2018
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
395 hp 5L V8
Exterior color:
Oxford White
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Medium Earth Gray
Transmission:
Automatic
Mileage:
131,141
Stock number:
U523A
VIN:
1FTEW1E55JKD50356

Preparing for a close up...

Photos coming soon

2024 Ford F-150

XLT SuperCrew 4WD

58,570 miles

$30,908

Great Deal
Saint Cloud, FL
24 mi away
Year:
2024
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
Four-Wheel Drive
Engine:
430 hp 3.5L V6 Hybrid
Exterior color:
Carbonized Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Hybrid
Interior color:
Black/Slate Gray
Transmission:
Automatic
Mileage:
58,570
Stock number:
A35540N
VIN:
1FTFW3LD3RFA35540

Preparing for a close up...

Photos coming soon

2019 Chevrolet Silverado 2500HD

Work Truck Double Cab LB RWD

151,495 miles

$17,995

Great Deal
Winter Garden, FL
5 mi away
Year:
2019
Make:
Chevrolet
Model:
Silverado 2500HD
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
360 hp 6L V8 Flex Fuel Vehicle
Exterior color:
White
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray
Transmission:
6-Speed Automatic
Mileage:
151,495
Stock number:
25-0289
VIN:
2GC2CREG5K1227914

Preparing for a close up...

Photos coming soon

2020 Ford F-150

XL SuperCrew RWD

93,684 miles

$21,991

Fair Deal
Sanford, FL
24 mi away
Year:
2020
Make:
Ford
Model:
F-150
Body type:
Pickup Truck
Doors:
4 doors
Drivetrain:
4X2
Engine:
395 hp 5L V8 Flex Fuel Vehicle
Exterior color:
White
Combined gas mileage:
20 MPG
Fuel type:
Flex Fuel Vehicle
Interior color:
Gray
Transmission:
Automatic
Mileage:
93,684
Stock number:
C09110
VIN:
1FTEW1C55LFC09110

Sponsored

  1. Home
  2. / Used Cars
  3. / Pickup Truck
  4. / Florida
  5. / Windermere
Reviews

4.4 Overall rating

(24,303 reviews)
Anonymous
5.0
Reviewed a 2019 GMC AT4 Crew Cab 4WD on Sep 08, 2024

The truck had all the features I wanted and the price was in-line, or better with others in my search.

Mike B
5.0
Reviewed a 2020 Toyota Tundra on May 16, 2024

Great Vehicle reliability is great! I would recommend this truck to anyone who wants to be on a vehicle for the long haul.

Mel M
5.0
Reviewed a 2023 Ford F-150 Lightning on Apr 15, 2024

This has been my dream truck since it was created! I absolutely love this truck. Have owned many trucks but this by far beats my King Ranch that i previously owned.

Jordan D
4.0
Reviewed a 2011 RAM SLT Quad Cab 4WD on Jan 24, 2025

It is a nice truck worth the money and is a all around good year for dodge

Gael P
5.0
Reviewed a 2015 RAM Tradesman 4WD on Jan 15, 2025

Great value good features for year and overall amazing vehicle

  • Used Pickup Trucks for Sale Under $10,000 Near Windermere

  • Used Pickup Trucks for Sale Under $15,000 Near Windermere

  • Used Pickup Trucks for Sale Under $20,000 Near Windermere

  • Used Pickup Trucks for Sale Under $25,000 Near Windermere

  • Used Pickup Trucks for Sale Under $30,000 Near Windermere

  • Used Pickup Trucks for Sale Under $40,000 Near Windermere

  • Pickup Trucks in Orlando FL

  • Pickup Trucks in Leesburg FL

  • Pickup Trucks in Lakeland FL

  • Pickup Trucks in Titusville FL

  • Pickup Trucks in Brooksville FL

  • Pickup Trucks in Daytona Beach FL

  • Pickup Trucks in Ocala FL

  • Pickup Trucks in Melbourne FL

  • Pickup Trucks in Tampa FL

  • Old Chevy Trucks for Sale in Windermere FL

  • RAM Trucks for Sale in Windermere FL - CarGurus

  • Ford Trucks for Sale in Windermere FL

  • Lifted GMC trucks for sale in Windermere FL

  • Chevrolet Trucks For Sale in Windermere FL

  • Old Toyota Pickups for Sale in Windermere FL

  • Dodge and RAM Trucks for Sale by Owner in Windermere FL

  • Classic Ford Trucks for Sale in Windermere FL

  • Dodge Trucks For Sale in Windermere FL

  • Toyota Trucks for Sale in Windermere FL

  • Ford F-150 in Windermere FL

  • Chevrolet Silverado 1500 in Windermere FL

  • RAM 1500 in Windermere FL

  • GMC Sierra 1500 in Windermere FL

  • Toyota Tacoma in Windermere FL

  • Ford F-250 Super Duty in Windermere FL

  • RAM 2500 in Windermere FL

  • Jeep Compass in Windermere FL

  • Ford Maverick in Windermere FL

  • Chevrolet Silverado 2500HD in Windermere FL

  • Ford Transit Cargo in Windermere FL

  • Ford F-350 Super Duty in Windermere FL

  • Used Electric Pickup Trucks for Sale

  • 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

  • Mint Auto Sales

  • Holler Driver's Mart Winter Park

  • Mullinax Ford of Central Florida

  • Starling Chevrolet of Orlando

  • HGreg Lux Orlando

  • Holler Ford

  • Jaguar Land Rover Lakeland

  • AutoNation Toyota Winter Park

  • Orlando Autohub Inc

  • Starling Chevrolet GMC

  • Holler Driver's Mart Sanford

  • Carroll Chevrolet

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.