Used 2019 Toyota Highlander for Sale nearChicago, IL
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Silver
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 96,004
- Stock #:
- JYC-921119
- VIN:
- 5TDBZRFH4KS921119


Sponsored by Your Choice Autos - Joliet
2019 Toyota Highlander
LE AWD
96,004 mi
$22,999
- 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:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 99,148
- Stock #:
- ND3700
- VIN:
- 5TDJZRFH0KS602215

Sponsored Listing
2019 Toyota Highlander
XLE AWD
99,148 mi
$25,370
- 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
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 44,498
- Stock #:
- 5037
- VIN:
- 5TDJZRFH2KS932115

Sponsored Listing
2019 Toyota Highlander
XLE AWD
44,498 mi
$28,795
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Tan)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 86,845
- Stock #:
- 34-26418A
- VIN:
- 5TDDZRFH7JS911644

2018 Toyota Highlander
Limited Platinum AWD
86,845 mi
$27,283
- 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:
- Salsa Red Pearl
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 97,457
- Stock #:
- J5385A
- VIN:
- 5TDJZRFH9KS609860

2019 Toyota Highlander
SE AWD
97,457 mi
$23,990
- 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:
- Shoreline Mist
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 105,745
- Stock #:
- 9633A
- VIN:
- 5TDDZRFH3JS831998

2018 Toyota Highlander
Limited AWD
105,745 mi
$24,323
- 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:
- Shoreline Blue Pearl
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 94,684
- Stock #:
- 101465
- VIN:
- 5TDZARFH5JS038974

2018 Toyota Highlander
LE
94,684 mi
$20,358
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 108,392
- Stock #:
- 34-26434A
- VIN:
- 5TDJZRFH0JS546274

2018 Toyota Highlander
XLE AWD
108,392 mi
$22,278
- 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:
- 8-Speed Automatic
- Mileage:
- 105,629
- Stock #:
- 1627
- VIN:
- 5TDKZRFH8JS532398

2018 Toyota Highlander
SE
105,629 mi
$22,320
- 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:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 27,428
- Stock #:
- T66251A
- VIN:
- 5TDDZRFH0KS958600

2019 Toyota Highlander
Limited AWD
27,428 mi
$34,278
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 90,561
- Stock #:
- H52005A
- VIN:
- 5TDJZRFH0KS967347

2019 Toyota Highlander
XLE AWD
90,561 mi
$25,907
- 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:
- Black
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 65,579
- Stock #:
- P3694A
- VIN:
- 5TDJZRFH6KS980331

2019 Toyota Highlander
SE AWD
65,579 mi
$28,389
- 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:
- 79,738
- Stock #:
- VM3077A
- VIN:
- 5TDCZRAH0LS021797

2020 Toyota Highlander
L FWD
79,738 mi
$23,278
CarGurus Analysis:
2019 Toyota Highlander
With 218 currently listed for sale near Chicago, IL and an average price of $36,063.00, 23.9% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.76 / 5 stars.
94.5% of 2019 Highlander models on CarGurus are accident free.
- 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:
- Ash
- Transmission:
- Automatic
- Mileage:
- 90,116
- Stock #:
- N260508B
- VIN:
- 5TDBZRFH1JS895707

2018 Toyota Highlander
LE Plus AWD
90,116 mi
$22,613
- 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:
- 8-Speed Automatic
- Mileage:
- 87,794
- Stock #:
- 9175
- VIN:
- 5TDJZRFH5JS826773

2018 Toyota Highlander
XLE AWD
87,794 mi
$22,956
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 110,058
- Stock #:
- PC882380
- VIN:
- 5TDDZRFH6JS882380

-$1,489
2018 Toyota Highlander
Limited AWD
110,058 mi
$21,119
$19,630
- 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:
- Moon Dust
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 101,086
- Stock #:
- AC260
- VIN:
- 5TDGZRAH9LS015546

2020 Toyota Highlander
XLE FWD
101,086 mi
$25,268
- 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:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 101,869
- Stock #:
- PH2083
- VIN:
- 5TDJZRFH4KS928860

2019 Toyota Highlander
XLE AWD
101,869 mi
$24,279
- 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 ME
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 101,513
- Stock #:
- 61448A
- VIN:
- 5TDDZRFH3KS919273

2019 Toyota Highlander
Limited Platinum AWD
101,513 mi
$28,411
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 98,738
- Stock #:
- 20160PA
- VIN:
- 5TDGZRAHXLS005401

2020 Toyota Highlander
XLE FWD
98,738 mi
$25,663
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- Automatic
- Mileage:
- 97,046
- Stock #:
- 10227
- VIN:
- 5TDKZRFH5JS534898

2018 Toyota Highlander
XLE
97,046 mi
$23,206
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 80,225
- Stock #:
- 10142K
- VIN:
- 5TDJZRFH6KS564313

-$500
2019 Toyota Highlander
SE AWD
80,225 mi
$26,074
$25,574
- 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 ME
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 101,513
- Stock #:
- 61448A
- VIN:
- 5TDDZRFH3KS919273

Sponsored Listing
2019 Toyota Highlander
Limited Platinum AWD
101,513 mi
$28,411
CarGurus Analysis: 2019 Toyota Highlander

Summary
With 218 currently listed for sale near Chicago, IL and an average price of $36,063.00, 23.9% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.76 / 5 stars.
94.5% of 2019 Highlander models on CarGurus are accident free.
Why it stands out
The 2019 Toyota Highlander continues to impress buyers with its spaciousness, comfort, and reliability, making it a strong contender in the midsize SUV market. This model is particularly noted for its excellent safety features and overall performance, which have garnered high praise from owners. While some users have expressed a desire for more rear seat space and have pointed out its higher price point, the Highlander remains a practical choice for families. The vehicle's smooth ride and quiet cabin contribute to a pleasant driving experience, although it may not excite those looking for sporty handling. Overall, the Highlander balances comfort and utility, making it a solid investment for those in need of a reliable family vehicle.
Other model years to consider
- Average price: $34,000.00
- Good/great deal percentage: 29.2%
- User rating: 4.93 / 5
- Total listings: 154
- Average price: $45,000.00
- Good/great deal percentage: 43.2%
- User rating: 4.75 / 5
- Total listings: 257
- Average price: $39,000.00
- Good/great deal percentage: 34.4%
- User rating: 4.86 / 5
- Total listings: 241
This analysis is based on CarGurus' proprietary market data from July 21, 2026, CarGurus experts' opinions, and generative AI.
4.8 Overall rating
Filter by rating
Simone P
Reviewed a 2019 Toyota SE FWD on Aug 10, 2025
I just purchased a pre-owner Toyota Highlander. I picked the 2019 model because it is the last model year that had the rear window that opened independently from the lift gate. I missed that feature in my last two Honda CRV’s because the older (gen 1 &2) Honda CRV’s used to have that feature too. Both the CRV and Highlander have similar features and are both reliable and wonderful cars, which will last a long time. I just needed a larger car for my current needs. The Honda did get better gas mileage than the Toyota, but it was also a smaller SUV. I have owned different Honda CR-Vs for the last 30 years, and have been very happy with them. This is my first Toyota. The Highlander is very comfortable and roomy. My daughter really likes the captain’s seats in the back. I am very happy with the Highlander and plan to have it for many years.
Anonymous
Reviewed a 2019 Toyota Highlander on Sep 3, 2024
great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort
Dennis G
Reviewed a 2019 Toyota Limited AWD on Mar 27, 2025
Comfortable, strong and stylish. Plenty of room for wife's wheel chair, her and myself along with what ever else we need to transport. Did have a problem starting once after sitting 3 weeks unproven. Small portable starter was very handy, started right up. No issues since. Lot of safety reminders, clearance between you and car in front of you in cruse control, out of lane warning. Wish it had digital speed display. Nav works well. I have SiriusXM radio, killer sound.
Suzanne M
Reviewed a 2019 Toyota Highlander on Oct 11, 2024
It’s roomy, has all the bells and whistles. Nice smooth ride. Takes a little time to manipulate all the “bells and whistles”. Also aesthetically good .
2019 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Limited FWD | $42,930 |
| Limited Platinum AWD | $47,510 |
| LE AWD | $35,340 |
| Limited AWD | $44,390 |
| SE AWD | $42,400 |
| LE FWD | $33,880 |
| XLE FWD | $39,720 |
| XLE AWD | $41,180 |
2019 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2019 Toyota Highlander prices has changed over time.
See more price trends2019 Toyota Highlander Pricing Analysis: Chicago, IL Market Report
Pricing by Nearby Locations
Market Area: Chicago, IL
Key Insights
- Highest Prices in South Bend: The market in South Bend, IN ($28,708) shows the highest average price, likely due to limited inventory and higher demand.
- Lowest Prices in Milwaukee: Milwaukee, WI ($23,804) offers the lowest average price, indicating a more competitive market with higher inventory levels.
- Inventory Variation: Cities like Palatine (202 listings) and Aurora (209 listings) have substantial inventory, which correlates with average prices around $25K, suggesting stable pricing dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| South Bend, IN | 186 | $28,708 |
| Aurora, IL | 209 | $25,533 |
| Palatine, IL | 202 | $25,138 |
| Kenosha, WI | 201 | $25,898 |
| Rockford, IL | 181 | $24,030 |
| Janesville, WI | 185 | $24,174 |
| Holland, MI | 187 | $23,970 |
| Kalamazoo, MI | 192 | $24,055 |
| Lafayette, IN | 200 | $26,217 |
| Milwaukee, WI | 180 | $23,804 |
Pricing by Trim Packages
Key Insights
- AWD Trims Lead Inventory: The XLE AWD (255 listings) is the most common trim, reflecting strong demand for all-wheel drive options in the region.
- Premium Pricing for Limited Trims: The Limited AWD ($44,390 MSRP) commands a significant premium, indicating a market preference for luxury features.
- Value in Base Trims: The LE AWD ($35,340 MSRP) offers a competitive entry point for buyers seeking AWD capabilities without the luxury markup.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 255 | $41,180 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 117 | $44,390 | AWD | 3.5L 295 hp V6 |
| LE AWD | 50 | $35,340 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 65 | $39,720 | FWD | 3.5L 295 hp V6 |
| LE FWD | 36 | $33,880 | FWD | 3.5L 295 hp V6 |
| Limited FWD | 25 | $42,930 | FWD | 3.5L 295 hp V6 |
| Limited Platinum AWD | 25 | $47,510 | AWD | 3.5L 295 hp V6 |
| SE AWD | 37 | $42,400 | AWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Newer Models Retain Value: The 2026 Highlander is priced at $43,899, which is about -4.0% below MSRP, indicating strong demand for the latest models.
- Significant Depreciation for Older Models: The 2015 Highlander shows a steep decline, priced at $18,507, reflecting a -37.5% depreciation from its original MSRP.
- Best Value in Mid-Age Models: The 2021 Highlander is priced at $30,075, representing a -14.3% depreciation, making it a compelling option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 | $46,270 | $43,899 | -4.0% |
| 2025 | $40,320 | $39,702 | -1.5% |
| 2024 | $39,270 | $37,119 | -5.5% |
| 2023 | $36,620 | $34,934 | -4.6% |
| 2022 | $35,855 | $35,041 | -2.3% |
| 2021 | $35,085 | $30,075 | -14.3% |
| 2020 | $34,600 | $25,656 | -26.0% |
| 2019 | $31,230 | $22,588 | -27.7% |
| 2018 | $30,630 | $20,128 | -34.3% |
| 2015 | $29,765 | $18,507 | -37.5% |
These recommendations are based on CarGurus' proprietary market data from July 23, 2026, CarGurus experts' opinions, and generative AI.
How much does the 2019 Toyota Highlander cost?
| Metric | Value |
|---|---|
| Current Average Price | $24,257 |
| Year-Round Low | $23,073.34 |
| Year-Round High | $25,437.96 |
| Average Price a Year Ago | $25,436 |
| Change vs. Last Year | −4.64% |
Prices have softened 4.64% compared to this time last year, making it a favorable time to shop this model year.
There are 2,694 listings available, which gives you a solid amount of inventory to compare.
If you find a listing below $23,073.34, that's toward the low end of the year-round range and worth acting on quickly.
Is the 2019 Toyota Highlander a good car?
Yes — the 4.76/5 user rating points to strong owner satisfaction. Drivers consistently praise its comfort, spaciousness, and reliability, and many also like the safety features and engine performance. For you, that makes it a strong fit if you want a family-friendly midsize SUV with a practical, easygoing character. With 32.9% of listings marked as good or great deals, you still have room to shop selectively.
Is the 2019 Toyota Highlander reliable?
Owners rate it 4.76/5, a strong signal of long-term satisfaction.
The user feedback highlights reliability, and drivers also describe it as dependable and trouble-free over time. That kind of feedback matters if you want a used SUV you can count on for daily family use and longer ownership. For used buyers, the main long-term risk is paying too much for a vehicle whose condition or history has not been carefully verified.
What should I look for when buying a used 2019 Toyota Highlander?
At 65.7% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
You should start with a vehicle history report so you can screen for accidents, title issues, and ownership patterns before you get too far into the process. After that, prioritize a pre-purchase inspection, especially if the listing price looks unusually attractive. Focus your condition check on signs of prior repair quality, wear consistency, and whether the vehicle feels as well-kept as the seller claims.
Is now a good time to buy a used 2019 Toyota Highlander?
This looks like a moderate, selective buyer's market, so you can shop carefully without feeling rushed.
- Deal availability: 32.9% of listings are priced as good or great deals.
- Inventory: There are 2,694 listings available.
- Price trend: Prices have softened 4.64% compared with last year.
- Clean inventory: 65.7% of listings are accident-free.
If you find a listing below $23,073.34, that's toward the low end of the year-round range and worth acting on quickly.
What is the 2019 Toyota Highlander's resale value?
The current average of $24,257 sits slightly below last year's $25,436.
That softer pricing can help you buy at a more favorable entry point, but it also suggests resale upside may be more measured than in a rising market. If you plan to sell later, condition and documentation will matter more because buyers will have plenty of comparable listings to choose from. A well-kept example should still hold appeal thanks to steady demand for practical family SUVs.
Vehicles with strong owner satisfaction ratings, like this model year's 4.76/5, tend to retain buyer demand, which supports resale value over time.
Should I buy a 2019 Toyota Highlander or consider a different year?
If you're weighing the 2019 against nearby model years, here's how to think about it:
Choose the 2019 if:
- 32.9% of listings are priced as good or great deals.
- At 65.7% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
- Price trend: Prices have softened 4.64% compared with last year.
- Owners rate it 4.76/5 — a strong satisfaction signal.
Consider the 2020 if:
- At $28,019, the 2020 costs more than the current year's $24,257 average.
- It was redesigned for a quieter, more premium-feeling cabin.
The bottom line: You should start with the 2019 if value matters most, because it combines a lower average price with strong owner satisfaction and decent deal availability. If you want the newer redesign and are willing to pay more, the 2020 is the better secondary path for buyers who prioritize a more upscale feel.
These recommendations are based on CarGurus' proprietary market data from July 22, 2026, CarGurus experts' opinions, and generative AI.
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