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Used 2020 Toyota Highlander for Sale near Winter Haven, FL

221 results
Winter Haven, FL
2020 Toyota Highlander XLE FWD Orlando Preowned

2020 Toyota Highlander

XLE FWD

77,387 miles

$26,598

Fair Deal
Orlando, FL
38 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blueprint
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
77,387
Stock number:
023782
VIN:
5TDGZRAH6LS023782

Sponsored

2020 Toyota Highlander L FWD

2020 Toyota Highlander

L FWD

133,150 miles

$16,999

Fair Deal
Lakeland, FL
16 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Black
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
133,150
Stock number:
LS014171
VIN:
5TDCZRAH0LS014171

Sponsored

2020 Toyota Highlander XLE FWD

2020 Toyota Highlander

XLE FWD

96,170 miles

$22,231

Good Deal
Certified Pre-Owned
Tampa, FL
46 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
96,170
Stock number:
LS023832P
VIN:
5TDGZRAH6LS023832

Sponsored

2019 Toyota Highlander Limited AWD

2019 Toyota Highlander

Limited AWD

88,823 miles

$25,997

Fair Deal
Store transfer to Orlando, FL
867 mi away • Price includes $999 shipping Price includes $999 shipping
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red (Burgundy)
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
CREAM
Transmission:
Automatic
Mileage:
88,823
Stock number:
27645103
VIN:
5TDDZRFH8KS992560

2019 Toyota Highlander Limited FWD

2019 Toyota Highlander

Limited FWD

102,813 miles

$19,749

Great Deal
Orlando, FL
31 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
White (Blizzard Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
102,813
Stock number:
I620797A
VIN:
5TDYZRFH3KS298389

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2019 Toyota Highlander

LE FWD

137,817 miles

$12,999

Great Deal
Seffner, FL
36 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
137,817
Stock number:
P75664
VIN:
5TDZZRFH7KS301086

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2021 Toyota Highlander

XSE AWD

90,265 miles

$25,500

Great Deal
Tampa, FL
49 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
8-Speed Automatic
Mileage:
90,265
Stock number:
S594941A
VIN:
5TDJZRBH4MS133137

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2019 Toyota Highlander

Limited FWD

107,149 miles

$19,990

Great Deal
Orlando, FL
32 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
107,149
Stock number:
305696
VIN:
5TDKZRFH8KS305696

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2020 Toyota Highlander

XLE AWD

53,924 miles

$28,723

Good Deal
Certified Pre-Owned
Tampa, FL
49 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
53,924
Stock number:
LS521018
VIN:
5TDHZRBH1LS521018

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2020 Toyota Highlander

LE FWD

89,211 miles

$21,597

Good Deal
Wesley Chapel, FL
41 mi away
Year:
2020
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
89,211
Stock number:
D001340
VIN:
5TDZZRAH6LS001340

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2019 Toyota Highlander

LE FWD

107,434 miles

$16,981

Good Deal
Tampa, FL
40 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
107,434
Stock number:
B045676A
VIN:
5TDZZRFHXKS355952

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2021 Toyota Highlander

XLE FWD

52,225 miles

$26,900

Great Deal
Orlando, FL
34 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red (Ruby Flare Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
8-Speed Automatic
Mileage:
52,225
Stock number:
U041373
VIN:
5TDGZRAH0MS041373

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2019 Toyota Highlander

XLE FWD

68,311 miles

$23,752

Fair Deal
Clermont, FL
33 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
68,311
Stock number:
LE48129A
VIN:
5TDKZRFH0KS343164

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2021 Toyota Highlander

XLE FWD

105,446 miles

$22,999

Good Deal
Winter Park, FL
45 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
105,446
Stock number:
MS079869
VIN:
5TDGZRAHXMS079869

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2019 Toyota Highlander

XLE FWD

110,596 miles

$18,506

Great Deal
Orlando, FL
29 mi away
Year:
2019
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Ooh La La Rouge Mica
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Brown (Saddle Tan)
Transmission:
8-Speed Automatic
Mileage:
110,596
Stock number:
KS322564
VIN:
5TDKZRFHXKS322564

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  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / 2020
  5. / Florida
  6. / Winter Haven
Overview
Reviews
FAQs

CarGurus Analysis: 2020 Toyota Highlander

Picture of 2020 Toyota Highlander

Summary

  • With 3,587 currently listed for sale on CarGurus and an average price of $27,857.10, 35.7% of 2020 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2020 Toyota Highlander 4.5 / 5 stars and CarGurus experts gave it an 7.7 / 10.
  • 73% of 2020 Highlander models on CarGurus are accident free.
  • The 2020 Toyota Highlander excelled in passenger comfort with its tranquil interior, soft ride, and advanced safety features, making it a top choice in the midsize SUV segment.

Why it stands out

The 2020 Toyota Highlander distinguished itself with a premium feel that rivaled luxury vehicles like Lexus, especially in its upper trims. It provided a remarkably quiet and smooth ride, enhancing passenger comfort across all three rows. Additionally, the Highlander came equipped with standard advanced safety features, making it a practical choice for families seeking both space and peace of mind.

Other model years to consider

  • 2022 Toyota Highlander: This year offers $33,572.41 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,308 listings.
  • 2021 Toyota Highlander: This year offers $30,215.79 average price, 36% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,417 listings.
  • 2023 Toyota Highlander: This year offers $35,244.49 average price, 35% good/great deals, 4.4/5 user rating, 6,084 listings.

This analysis is based on CarGurus' proprietary market data from December 16, 2025, CarGurus experts' opinions, and generative AI.

4.5 Overall rating

(33 reviews)
Karen D
4.0
Reviewed a 2020 Toyota Highlander on Mar 11, 2024

The 2020 Toyota Highlander XLE drives great!! Very smooth ride and great acceleration. I loved how it could turn tight corners, like when pulling out onto a 4-lane road. A lot of great features. The sound system was ok, but realized it wasnt that great after comparing it to the 2021 Limited with JBL speakers. Wish it had the nicer sound system. There were two things I was very disappointed in. The seats seemed rather shallow, compared to the seats in my 2012 Limited Highlander. My friend and I both felt like we were sliding off the edge of the front seats. Does Toyota think that Americans are getting smaller? The other thing was that the visors were not long enough to come all the way out to the edge of the windshield. There was at least a two inch gap between the outside edge of the visor and the outside edge of the windshield!! What the heck were they thinking! Driving toward the sun in the late afternoon was terrible because the sun was in my eyes and there was nothing I could do about it. Again, my 2012 Highlander has this one beat because the visor is plenty long enough. What a stupid place to try to save a buck! Those two things have me looking at other vehicles because I dont want to settle for something that is uncomfortable, and when you pay 40K for a vehicle, it better be good in every aspect!

Anonymous
5.0
Reviewed a 2020 Toyota Highlander on Nov 07, 2020

Most comfortable riding vehicle that we have ever purchased. Great features and a great looking vehicle as well.

Kris B
5.0
Reviewed a 2020 Toyota Highlander on May 22, 2023

Absolutely love this car. Great comfortable family vehicle with plenty of space, and features

Lee W
4.0
Reviewed a 2020 Toyota Highlander on Feb 27, 2020

The ride was smooth, the Highlander is quick and very quiet. I loved many of the features it had, like the posted speed limit on the instrument cluster. What really disappointed me was the passenger seat comfort. The seat bottom only adjusts fron-to-rear, not up or down so I wasn’t as comfortable in it as I was the Hyundai Palisade or the Kia Telluride. It’s still a really good vehicle.

Becky S
5.0
Reviewed a 2020 Toyota Highlander on Nov 22, 2022

Just picked one up Saturday! Absolutely love it, love the features, everything about it. Love the 3 row seats for all the grandkids. Had a Lexus RX350, feel there very similar just a little more room in the Highlander. Levy’s very smooth driving though.

2020 Toyota Highlander FAQs

How much does the 2020 Toyota Highlander cost in Winter Haven, FL?

The average 2020 Toyota Highlander costs about $27,748.42. The average price has decreased by -7.4% since last year. The 220 for sale near Winter Haven, FL on CarGurus, range from $12,999 to $42,998 in price.

Is the 2020 Toyota Highlander a good car?

CarGurus experts gave the 2020 Toyota Highlander an overall rating of 7.7/10 and 2020 Toyota Highlander owners have rated the vehicle a 4.5/5 stars on average. If a vehicle has both strong expert and owner reviews, you can feel confident in its quality. If either expert reviews, owner reviews, or both are spotty, you might want to do some research to figure out where the car falls short.

How many 2020 Toyota Highlander vehicles in Winter Haven, FL have no reported accidents or damage?

220 out of 220 for sale near Winter Haven, FL have no reported accidents or damage.

Is the 2020 Toyota Highlander safe?

CarGurus experts gave the 2020 Toyota Highlander a safety rating of 9/10.

What is the fuel economy of the 2020 Toyota Highlander?

Depending on the engine and options, the 2020 Toyota Highlander gets between 22 and 23 MPG (or MPGe).

What fuel types are available?

Gasoline engines are available.

  • 2023 Toyota Highlander in Winter Haven FL

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