Used Toyota Highlander for Sale nearStockbridge, WI
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 58,017
- Stock #:
- T16593B
- VIN:
- 5TDKDRAH3PS020031
Sponsored by Toyota of Brookfield
2023 Toyota Highlander
LE FWD
58,017 mi
$28,513
- 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:
- ASH
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,336
- Stock #:
- 2954A
- VIN:
- 5TDBZRFH7KS992296
Sponsored Listing
2019 Toyota Highlander
LE Plus AWD
95,336 mi
$23,494
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 44,295
- Stock #:
- 260765A
- VIN:
- 5TDKDRBH6PS040286
Sponsored Listing
2023 Toyota Highlander
XLE AWD
44,295 mi
$37,277
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 16,791
- Stock #:
- 70115656
- VIN:
- 5TDKDRBH5RS564970
2024 Toyota Highlander
XLE AWD
16,791 mi
$44,247
- 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:
- 95,149
- Stock #:
- T260447A
- VIN:
- 5TDJZRFH9JS826548
2018 Toyota Highlander
XLE AWD
95,149 mi
$24,383
- 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:
- OOH LA LA ROUGE MICA
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 80,787
- Stock #:
- TT260924AA
- VIN:
- 5TDJZRFH0JS840063
2018 Toyota Highlander
XLE AWD
80,787 mi
$25,279
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 120,556
- Stock #:
- EP3977A
- VIN:
- 5TDDZRFH8JS914956
2018 Toyota Highlander
Limited AWD
120,556 mi
$22,594
- 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:
- Black
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 38,915
- Stock #:
- 28846910
- VIN:
- 5TDJZRBH6MS148657
2021 Toyota Highlander
XSE AWD
38,915 mi
$38,997
- 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:
- Red
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 93,989
- Stock #:
- 26C546B
- VIN:
- 5TDBKRFH4GS305786
2016 Toyota Highlander
LE Plus AWD
93,989 mi
$21,384
- 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:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,325
- Stock #:
- M54632
- VIN:
- 5TDDZRFH0KS950383
2019 Toyota Highlander
Limited Platinum AWD
78,325 mi
$29,719
- 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:
- 58,017
- Stock #:
- T16593B
- VIN:
- 5TDKDRAH3PS020031
2023 Toyota Highlander
LE FWD
58,017 mi
$28,513
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Opulent Amber
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,116
- Stock #:
- L21707A
- VIN:
- 5TDHZRBH8NS192045
2022 Toyota Highlander
XLE AWD
56,116 mi
$34,009
- Year:
- 2013
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Brown (Sand Beige)
- Transmission:
- 5-Speed Automatic Overdrive
- Mileage:
- 75,071
- Stock #:
- P23155
- VIN:
- 5TDBK3EH7DS221858
2013 Toyota Highlander
AWD
75,071 mi
$17,498
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 3,719 currently listed for sale and an average price of $39,125.00, 34.0% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.0% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,877
- Stock #:
- 3400
- VIN:
- 5TDJZRFH9KS616551
2019 Toyota Highlander
XLE AWD
85,877 mi
$27,148
- 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:
- 100,880
- Stock #:
- T1613A
- VIN:
- 5TDBZRBH1LS508422
2020 Toyota Highlander
LE AWD
100,880 mi
$24,294
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,490
- Stock #:
- PRS2902
- VIN:
- 5TDKDRBH4PS044756
2023 Toyota Highlander
XLE AWD
34,490 mi
$37,290
- 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:
- Blueprint
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 63,298
- Stock #:
- T-12111-A
- VIN:
- 5TDGZRBH7LS015091
2020 Toyota Highlander
XLE AWD
63,298 mi
$29,371
- 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:
- Ooh La La Rouge Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,938
- Stock #:
- P30427A
- VIN:
- 5TDJZRFH8JS842739
2018 Toyota Highlander
XLE AWD
95,938 mi
$23,514
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 97,385
- Stock #:
- F39540P
- VIN:
- 5TDJZRFH0KS617572
2019 Toyota Highlander
XLE AWD
97,385 mi
$26,363
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Shoreline Mist
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 125,767
- Stock #:
- 29713A
- VIN:
- 5TDDKRFHXFS151799
2015 Toyota Highlander
Limited AWD
125,767 mi
$19,215
- 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:
- ASH
- Transmission:
- 8-Speed Automatic
- Mileage:
- 95,336
- Stock #:
- 2954A
- VIN:
- 5TDBZRFH7KS992296
2019 Toyota Highlander
LE Plus AWD
95,336 mi
$23,494
- Year:
- 2015
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- White
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 131,240
- Stock #:
- 64128
- VIN:
- 5TDBKRFH9FS141269
2015 Toyota Highlander
131,240 mi
$17,344
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 17,748
- Stock #:
- P22897
- VIN:
- 5TDKDRBH6PS030289
Sponsored Listing
2023 Toyota Highlander
XLE AWD
17,748 mi
$39,097
FAQs
How much does the Toyota Highlander cost in Stockbridge, WI?
How many Toyota Highlander vehicles in Stockbridge, WI have no reported accidents or damage?
What fuel types are available?
4.7 Overall rating
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.
Filter by year
Filter by rating
What people say
Anonymous
Reviewed a 2024 Toyota XLE AWD on Dec 10, 2025
The 2024 Toyota Highlander XLE offers insane cabin room, comfort and luxury feel. The chassis makes an absolute smooth, dream and comfortable ride. Cabin rear chairs makes four adults feel like your in a Sequoia with room. Absolute beautiful and enjoyable ride and purchase
Erdem S
Reviewed a 2022 Toyota Limited FWD on Jul 15, 2026
Outstanding reliability record. One of the most dependable midsize SUVs ever built. Excellent resale value.
Luong S
Reviewed a 2012 Toyota Base on Apr 26, 2026
This car's features are very good and have great value the only missing is it has only one key.
Sarah T
Reviewed a 2020 Toyota Highlander on Dec 7, 2025
It’s well-equipped, comfortable, and family-friendly SUV with strong safety tech, a smooth ride, and premium touches (thanks to the platinum trim) like a panoramic moonroof, leather seating, and 12” touchscreen. Its V6 offers solid power and decent fuel efficiency for a 3-row SUV, and overall it feels modern, quiet, and refined. It’s a great value if you want a reliable, upscale daily driver! The main thing it’s missing is more usable third-row and cargo space. The 3rd row is tight for adults and cargo behind it is limited. Otherwise, it’s a strong all-around pick and fits exactly what I was looking for. I would compare this to the Kia Telluride, Hyundai Palisade, Honda Pilot, and the Ford Explorer.
Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of Toyota Highlander prices has changed over time.
See more price trendsToyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Toyota Highlander is priced at $52,195, reflecting a 12.6% increase over its MSRP, indicating strong demand for the latest model.
- Steep Depreciation for Older Models: The 2016 Highlander shows the most significant depreciation at -38.6% compared to its original MSRP, highlighting the rapid value loss in older vehicles.
- Best Value Year: The 2021 model is currently priced at $30,794, representing a -12.8% depreciation, making it a potentially attractive option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $52,195 | +12.6% |
| 2025 Toyota Highlander | $40,320 | $41,395 | +2.7% |
| 2024 Toyota Highlander | $39,270 | $39,217 | -0.1% |
| 2023 Toyota Highlander | $36,620 | $36,118 | -1.4% |
| 2022 Toyota Highlander | $35,855 | $33,752 | -5.9% |
| 2021 Toyota Highlander | $35,085 | $30,794 | -12.8% |
| 2020 Toyota Highlander | $34,600 | $28,502 | -17.7% |
| 2019 Toyota Highlander | $31,830 | $24,243 | -23.9% |
| 2018 Toyota Highlander | $31,230 | $22,413 | -28.3% |
| 2017 Toyota Highlander | $30,630 | $21,000 | -31.7% |
| 2016 Toyota Highlander | $30,490 | $18,750 | -38.6% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in New York: The New York, NY market commands the highest average price at $26,343, likely due to higher demand and lower inventory.
- Lowest Prices in Chicago: Chicago, IL offers the most competitive pricing at $24,441, suggesting a more price-sensitive market with higher inventory levels.
- Price Variation Across Cities: The average prices range from $24,441 in Chicago to $28,094 in Philadelphia, indicating regional differences in demand and supply dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 623 | $26,343 |
| Los Angeles, CA | 512 | $25,822 |
| Chicago, IL | 336 | $24,441 |
| Dallas, TX | 346 | $27,231 |
| Philadelphia, PA | 284 | $28,094 |
| Houston, TX | 352 | $25,014 |
| Miami, FL | 206 | $29,375 |
| Washington, DC | 457 | $26,857 |
| Atlanta, GA | 335 | $26,920 |
| Boston, MA | 603 | $27,856 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Inventory: The XLE AWD trim leads with 3,148 listings, indicating strong consumer preference for this configuration.
- Premium Pricing for Limited AWD: The Limited AWD trim, priced at $50,725, reflects a significant markup due to its luxury features, appealing to buyers seeking higher-end options.
- Consistent Features Across Trims: All trims offer similar popular features, such as backup cameras and adaptive cruise control, suggesting that buyers can expect a high level of standard equipment regardless of the trim chosen.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3148 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1212 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 703 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 549 | $53,925 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from July 16, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 3,719 currently listed for sale and an average price of $39,125.00, 34.0% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.0% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
Why it stands out
The 2024 Toyota Highlander continues to build on its reputation as a reliable and family-friendly SUV. With its spacious interior and comfortable seating for up to eight passengers, it is designed to accommodate families and their gear with ease. The Highlander is equipped with a suite of advanced safety features, including Toyota Safety Sense, which enhances driver confidence. Its smooth ride and refined handling make it a pleasure to drive, while the availability of hybrid models offers excellent fuel efficiency. Overall, the Highlander is a well-rounded vehicle that appeals to buyers looking for practicality and comfort.
Other model years to consider
- Average price: $36,026.00
- Good/great deal percentage: 34.3%
- User rating: 4.75 / 5
- Total listings: 4,322
- Average price: $30,397.00
- Good/great deal percentage: 34.5%
- User rating: 4.86 / 5
- Total listings: 3,221
- Average price: $33,381.00
- Good/great deal percentage: 34.2%
- User rating: 4.5 / 5
- Total listings: 4,694
These recommendations are based on CarGurus' proprietary market data from July 20, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$32,997
- User rating4.5
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$27,828
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,157
- User rating4.8636
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