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 Toyota Highlander for Sale near Windermere, FL

214 results
Windermere, FL
2023 Toyota Highlander XSE FWD Napleton Chrysler Jeep Dodge Ram Kissimmee

2023 Toyota Highlander

XSE FWD

125,605 miles

$25,754

Good Deal
Kissimmee, FL
14 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 (Wind Chill Pearl)
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
125,605
Stock number:
PS024943
VIN:
5TDKDRAH0PS024943

Sponsored

2019 Toyota Highlander Limited FWD

2019 Toyota Highlander

Limited FWD

51,456 miles

$27,991

Fair Deal
Clermont, 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:
White (Blizzard Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Ash
Transmission:
8-Speed Automatic
Mileage:
51,456
Stock number:
RF46441A
VIN:
5TDYZRFH3KS310590

Sponsored

2020 Toyota Highlander LE FWD

2020 Toyota Highlander

LE FWD

102,774 miles

$19,999

Good Deal
Lake Wales, FL
42 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:
White (Blizzard Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
102,774
Stock number:
5K26178A
VIN:
5TDZZRAH5LS507869

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

2019 Toyota Highlander Limited AWD

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

2006 Toyota Highlander Sport V6

2006 Toyota Highlander

Sport V6

232,397 miles

$3,000

Fair Deal
Orlando, FL
18 mi away
Year:
2006
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
215 hp 3.3L V6
Exterior color:
Black
Combined gas mileage:
20 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
5-Speed Automatic
Mileage:
232,397
VIN:
JTEGP21A360103575

Preparing for a close up...

Photos coming soon

2011 Toyota Highlander

Limited 4WD

143,356 miles

$6,995

Great Deal
Plant City, FL
47 mi away
Year:
2011
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Silver
Combined gas mileage:
19 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
143,356
Stock number:
1253A
VIN:
5TDDK3EH0BS053065

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE FWD

50,614 miles

$27,998

Great Deal
Kissimmee, FL
14 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:
Celestial Silver Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
50,614
Stock number:
NS121749
VIN:
5TDGZRAH1NS121749

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE FWD

61,180 miles

$28,999

Good Deal
Orlando, FL
13 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:
Midnight Black Metallic
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
61,180
Stock number:
7217Q
VIN:
5TDGZRAH2NS539673

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

LE FWD

52,682 miles

$26,495

Great Deal
Sanford, FL
25 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

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

XLE FWD

57,833 miles

$32,997

Fair Deal
Store transfer to Orlando, FL
1,845 mi away • Price includes $1,999 shipping Price includes $1,999 shipping
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:
Black
Transmission:
Automatic
Mileage:
57,833
Stock number:
28018733
VIN:
5TDKDRAH2PS016925

Preparing for a close up...

Photos coming soon

2020 Toyota Highlander

LE FWD

102,774 miles

$19,999

Good Deal
Lake Wales, FL
42 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:
White (Blizzard Pearl)
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
8-Speed Automatic
Mileage:
102,774
Stock number:
5K26178A
VIN:
5TDZZRAH5LS507869

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

LE FWD

68,860 miles

$24,399

Good Deal
Lakeland, FL
38 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
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
68,860
Stock number:
NS552794
VIN:
5TDZZRAH1NS552794

Preparing for a close up...

Photos coming soon

2023 Toyota Highlander

Limited FWD

62,830 miles

$29,645

Great Deal
Orlando, FL
15 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 (Wind Chill Pearl)
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
Automatic
Mileage:
62,830
Stock number:
PS021791
VIN:
5TDKDRAHXPS021791

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

LE FWD

39,495 miles

$27,999

Great Deal
Orlando, FL
17 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
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
39,495
Stock number:
55534636
VIN:
5TDKDRAH4RS538569

Preparing for a close up...

Photos coming soon

2018 Toyota Highlander

SE

77,926 miles

$19,998

Great Deal
Orlando, FL
13 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

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

Platinum FWD

68,455 miles

$31,980

Good Deal
Fruitland Park, FL
35 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

Preparing for a close up...

Photos coming soon

2017 Toyota Highlander

XLE

120,347 miles

$20,247

Fair Deal
Store transfer to Orlando, FL
529 mi away • Price includes $249 shipping Price includes $249 shipping
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:
Silver
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray
Transmission:
Automatic
Mileage:
120,347
Stock number:
28127293
VIN:
5TDKZRFH9HS198960

Preparing for a close up...

Photos coming soon

2018 Toyota Highlander

SE

46,317 miles

$26,397

Fair Deal
Store transfer to Orlando, FL
1,031 mi away • Price includes $1,399 shipping Price includes $1,399 shipping
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:
Black
Transmission:
Automatic
Mileage:
46,317
Stock number:
27579064
VIN:
5TDKZRFH2JS280437

Preparing for a close up...

Photos coming soon

2020 Toyota Highlander

XLE FWD

85,066 miles

$23,200

Good Deal
Deland, FL
39 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

Preparing for a close up...

Photos coming soon

2024 Toyota Highlander

LE FWD

36,223 miles

$28,849

Great Deal
Orlando, FL
17 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:
Black
Combined gas mileage:
25 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
8-Speed Automatic
Mileage:
36,223
Stock number:
55030371
VIN:
5TDKDRAH3RS054750

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XSE FWD

69,667 miles

$28,999

Good Deal
Certified Pre-Owned
Lakeland, FL
39 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
Transmission:
Automatic
Mileage:
69,667
Stock number:
NS142650
VIN:
5TDLZRAH1NS142650

Preparing for a close up...

Photos coming soon

2022 Toyota Highlander

XLE FWD

63,978 miles

$29,495

Fair Deal
Eustis, FL
25 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
Combined gas mileage:
24 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
63,978
Stock number:
T6957A
VIN:
5TDGZRAH4NS544261

Sponsored

  1. Home
  2. / Used Cars
  3. / Toyota Highlander
  4. / Florida
  5. / Windermere
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 Windermere, FL?

The average Toyota Highlander costs about $27,405.38. The average price has decreased by -6.3% since last year. The 216 for sale near Windermere, FL on CarGurus, range from $3,000 to $53,998 in price.

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

216 out of 216 for sale near Windermere, FL have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

  • 2026 Toyota Highlander in Windermere FL

  • 2025 Toyota Highlander in Windermere FL

  • 2024 Toyota Highlander

  • 2023 Toyota Highlander

  • 2022 Toyota Highlander

  • 2021 Toyota Highlander

  • Used Toyota Highlander for Sale Under $10,000

  • Used Toyota Highlander for Sale Under $15,000

  • Used Toyota Highlander for Sale Under $20,000

  • Used Toyota Highlander for Sale Under $25,000

  • Used Toyota Highlander for Sale Under $30,000

  • Used Toyota Highlander for Sale Under $40,000

  • Used White Toyota Highlander for Sale

  • Used Blue Toyota Highlander for Sale

  • Used Red Toyota Highlander for Sale

  • Used Black Toyota Highlander for Sale

  • Used Silver Toyota Highlander for Sale

  • Used Gray Toyota Highlander for Sale

  • Toyota Highlander XLE AWD

  • Toyota Highlander XLE FWD

  • Toyota Highlander Limited AWD

  • Toyota Highlander LE AWD

  • Toyota Highlander LE FWD

  • Toyota Highlander XLE

  • Toyota Highlander Platinum AWD

  • Toyota Highlander XSE AWD

  • Toyota Highlander L FWD

  • Toyota Highlander Limited FWD

  • Toyota Sedans for Sale in Windermere FL

  • Toyota SUVs & Crossovers for Sale in Windermere FL

  • Old Toyota Pickups for Sale in Windermere FL

  • Used Toyota Electric Cars for Sale

  • Reliable Cars For Sale in Windermere FL

  • Toyota Trucks for Sale in Windermere FL

  • Best 3-Row SUVs For Sale in Windermere FL

  • Used Toyota Highlander for Sale with Low Mileage

  • Used SUVs / Crossovers for Sale with Low Mileage

  • New Toyota Highlander in Windermere FL

  • Certified Used Toyota Highlander in Windermere FL

  • Cadillac SRX in Windermere FL

  • Ford Escape in Windermere FL

  • Hyundai Veracruz in Windermere FL

  • Toyota Highlander in Orlando FL

  • Toyota Highlander in Leesburg FL

  • Toyota Highlander in Lakeland FL

  • Toyota Highlander in Titusville FL

  • Toyota Highlander in Brooksville FL

  • Toyota Highlander in Daytona Beach FL

  • Toyota Highlander in Ocala FL

  • Toyota Highlander in Melbourne FL

  • Toyota Highlander in Tampa FL

  • 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

  • AutoNation Toyota Winter Park

  • Phillips Toyota

  • Seminole Toyota

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

© 2025 CarGurus, Inc., All Rights Reserved.