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Used Toyota Highlander for Sale near Winter Park, FL

180 results
Winter Park, FL
2024 Toyota Highlander XLE FWD AutoNation Toyota Winter Park

2024 Toyota Highlander

XLE FWD

11,504 miles

$37,999

Fair Deal
Winter Park, FL
3 mi away
Year:
2024
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White (Wind Chill Pearl)
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Brown (Harvest Beige)
Transmission:
Automatic
Mileage:
11,504
Stock number:
RS548666
VIN:
5TDKDRAH8RS548666

Sponsored

2021 Toyota Highlander LE FWD

2021 Toyota Highlander

LE FWD

71,200 miles

$23,500

Good Deal
Sanford, FL
13 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:
Celestial Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
71,200
Stock number:
NU075111
VIN:
5TDZZRAH7MS075111

Sponsored

2005 Toyota Highlander Limited V6

2005 Toyota Highlander

Limited V6

123,892 miles

$5,500

Fair Deal
Orlando, FL
9 mi away
Year:
2005
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
230 hp 3.3L V6
Exterior color:
Gold
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Brown (BEIGE)
Transmission:
Automatic
Mileage:
123,892
Stock number:
13632
VIN:
JTEDP21A850048722

Sponsored

2022 Toyota Highlander L FWD

2022 Toyota Highlander

L FWD

42,678 miles

$24,999

Great Deal
Orlando, FL
12 mi away
Year:
2022
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
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
42,678
Stock number:
553113
VIN:
5TDCZRAH3NS553113

2021 Toyota Highlander XLE FWD

2021 Toyota Highlander

XLE FWD

39,926 miles

$27,980

Good Deal
Daytona Beach, FL
47 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:
Silver
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
39,926
Stock number:
G26093A
VIN:
5TDGZRAH8MS069695

2019 Toyota Highlander Limited Platinum AWD

2019 Toyota Highlander

Limited Platinum AWD

67,044 miles

$27,999

Good Deal
Leesburg, FL
33 mi away
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:
Midnight Black Metallic
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
67,044
Stock number:
260168A
VIN:
5TDDZRFH6KS707497

Preparing for a close up...

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2023 Toyota Highlander

LE FWD

52,682 miles

$26,295

Great Deal
Sanford, FL
13 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Celestial Silver Metallic
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
52,682
Stock number:
SD333489A
VIN:
5TDKDRAH2PS511609

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2017 Toyota Highlander

XLE AWD

104,296 miles

$21,547

Fair Deal
Store transfer to Orlando, FL
599 mi away • Price includes $549 shipping Price includes $549 shipping
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Silver
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
104,296
Stock number:
27852446
VIN:
5TDJZRFH7HS479327

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2019 Toyota Highlander

Limited AWD

88,823 miles

$25,997

Fair Deal
Store transfer to Orlando, FL
848 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

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2020 Toyota Highlander

XLE FWD

51,293 miles

$24,998

Great Deal
Orlando, FL
10 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:
Blue
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
51,293
Stock number:
S016643
VIN:
5TDHZRAH6LS016643

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2018 Toyota Highlander

SE

77,926 miles

$19,798

Great Deal
Orlando, FL
10 mi away
Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Gray
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
77,926
Stock number:
S279480
VIN:
5TDKZRFH9JS279480

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2019 Toyota Highlander

XLE FWD

68,311 miles

$23,692

Fair Deal
Clermont, FL
24 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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2022 Toyota Highlander

Platinum FWD

68,455 miles

$31,980

Good Deal
Fruitland Park, FL
40 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Opulent Amber 4x9
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
68,455
Stock number:
26199B
VIN:
5TDFZRAH2NS105300

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2016 Toyota Highlander

Limited AWD

112,210 miles

$18,991

Fair Deal
Leesburg, FL
33 mi away
Year:
2016
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Nautical Blue Metallic
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
6-Speed Automatic Overdrive
Mileage:
112,210
Stock number:
260228B
VIN:
5TDDKRFH2GS294859

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2019 Toyota Highlander

SE FWD

65,799 miles

$23,900

Good Deal
Clermont, FL
20 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:
Red
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
65,799
Stock number:
G709812A
VIN:
5TDKZRFH8KS339508

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2020 Toyota Highlander

XLE FWD

85,066 miles

$23,200

Good Deal
Deland, FL
27 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:
Red (Ruby Flare Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
85,066
Stock number:
LS510686
VIN:
5TDHZRAH7LS510686

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2018 Toyota Highlander

XLE

116,924 miles

$16,950

Great Deal
Winter Haven, FL
47 mi away
Year:
2018
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:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
116,924
Stock number:
JS535270
VIN:
5TDKZRFH8JS535270

Preparing for a close up...

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2019 Toyota Highlander

Limited FWD

107,149 miles

$19,990

Great Deal
Orlando, FL
12 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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2023 Toyota Highlander

LE FWD

33,621 miles

$28,500

Good Deal
Clermont, FL
20 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
Gray
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
33,621
Stock number:
S018224
VIN:
5TDKDRAH4PS018224

Preparing for a close up...

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2017 Toyota Highlander

SE

15,404 miles

$25,495

Good Deal
Winter Park, FL
3 mi away
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
15,404
Stock number:
W9273239A
VIN:
5TDKZRFH6HS508918

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2018 Toyota Highlander

SE AWD

47,788 miles

$25,999

Good Deal
Winter Park, FL
3 mi away
Year:
2018
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Predawn Gray Mica
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
47,788
Stock number:
JS496970
VIN:
5TDJZRFHXJS496970

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2012 Toyota Highlander

SE

173,250 miles

$7,777

Good Deal
Orlando, FL
3 mi away
Year:
2012
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
187 hp 2.7L I4
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Transmission:
6-Speed Automatic
Mileage:
173,250
Stock number:
RR-023479
VIN:
5TDZA3EH6CS023479

Preparing for a close up...

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2023 Toyota Highlander

XSE FWD

55,035 miles

$33,087

Fair Deal
Orlando, FL
5 mi away
Year:
2023
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
265 hp 2.4L I4
Exterior color:
White
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
55,035
Stock number:
PS508697
VIN:
5TDKDRAHXPS508697

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  1. Home
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  5. / Winter Park
Overview
Reviews
FAQs

CarGurus recommends the 2022 Toyota Highlander

Picture of Toyota Highlander

Summary

  • With 6,308 currently listed for sale on CarGurus and an average price of $33,572.40, 35.5% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
  • Favorably reviewed: Owners rated the 2022 Toyota Highlander 4.6 / 5 stars and CarGurus experts gave it an 8.2 / 10.
  • 83.7% of 2022 Highlander models on CarGurus are accident free.
  • The 2022 Toyota Highlander featured an impressive 84.3 cubic feet of cargo space with seats folded down, making it highly versatile for families and adventures.

Why it stands out

The 2022 Toyota Highlander stands out in the family SUV segment due to its spacious three-row seating, making it ideal for families needing ample room for passengers and cargo. It features a robust V6 engine that delivers reliable performance, coupled with standard safety technologies that enhance peace of mind on the road. With a variety of trims available, the Highlander caters to diverse preferences and budgets while maintaining Toyota's reputation for reliability and efficiency.

Other model years to consider

For buyers considering the Toyota Highlander, model years 2015 and 2021 stand out as attractive options. The 2015 Highlander combines a competitive average price with an impressive user rating of 4.8/5 and a high percentage of good deals, making it a strong value proposition for those seeking reliability and satisfaction. Similarly, the 2021 model offers modern features at a reasonable price point while maintaining high user satisfaction ratings, positioning it well in today’s marketplace.

Other noteworthy alternatives include the 2019 Highlander, which offers solid user feedback and value for money, as well as the 2016 version, which has an appealing price point along with high user ratings. These models collectively provide diverse options that cater to different budgets while ensuring consistent quality and satisfaction among users.

Model years to approach with caution

The Toyota Highlander model years 2014, 2018, and 2011 should be approached with caution due to several financial and quality considerations. Despite decent user ratings, a significant percentage of these models are categorized as not providing good or great deals, indicating potential overpricing in the market. Furthermore, as newer models become available, availability constraints for earlier years may limit options for buyers seeking a balance between quality and price.

These recommendations are based on CarGurus' proprietary market data from December 17, 2025, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(691 reviews)

Customers say

Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.

AI generated from the text of customer reviews.

What people say

cargo space comfort interior performance safety
Julie W
5.0
Reviewed a 2021 Toyota Highlander on Jul 20, 2024

I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.

Kristy E
5.0
Reviewed a 2010 Toyota Highlander on Jan 25, 2024

Great car that has a reputation for durability. Love the features.

Melissa C
5.0
Reviewed a 2021 Toyota Highlander on May 05, 2024

Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.

Emmanuel S
5.0
Reviewed a 2022 Toyota Highlander on Apr 18, 2024

The car is great with very nice features. It is a good value in terms of price and nothing is missing. It is a good looking car

Anonymous
5.0
Reviewed a 2019 Toyota Highlander on Sep 03, 2024

great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort

Toyota Highlander FAQs

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

The average Toyota Highlander costs about $27,252.19. The average price has decreased by -7% since last year. The 180 for sale near Winter Park, FL on CarGurus, range from $3,000 to $45,999 in price.

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

180 out of 180 for sale near Winter Park, FL have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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