Used Toyota Highlander for Sale near Madison, WI
340 results
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,777
- Stock #:
- T16844A
- VIN:
- 5TDGZRBH0MS155615
Sponsored by Toyota of Brookfield
2021 Toyota Highlander
XLE AWD
57,777 mi
$31,382
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Transmission:
- 5-Speed Automatic
- Mileage:
- 217,776
- Stock #:
- 11198
- VIN:
- 5TDBK3EHXCS152260
Sponsored Listing
2012 Toyota Highlander
SE AWD
217,776 mi
$8,144
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 40,747
- Stock #:
- PJR1501
- VIN:
- 5TDKDRBH9RS546794
Sponsored Listing
2024 Toyota Highlander
LE AWD
40,747 mi
$32,960
- 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:
- Blue
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 99,641
- Stock #:
- 28520857
- VIN:
- 5TDKZRFHXJS265393
2018 Toyota Highlander
XLE
99,641 mi
$23,797
- 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:
- Predawn Gray Mica
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 88,789
- Stock #:
- 101444
- VIN:
- 5TDDKRFH1FS122529
2015 Toyota Highlander
Limited AWD
88,789 mi
$19,980
- Year:
- 2025
- 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:
- 34,767
- Stock #:
- 24P4847
- VIN:
- 5TDKDRBHXSS579194
2025 Toyota Highlander
XSE AWD
34,767 mi
$42,014
- Year:
- 2014
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 135,997
- Stock #:
- K6090A
- VIN:
- 5TDDKRFH5ES046828
-$733
2014 Toyota Highlander
Limited Platinum AWD
135,997 mi
$17,491
$16,758
- 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:
- Midnight Black Metallic
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 70,088
- Stock #:
- X026945A
- VIN:
- 5TDDKRFH2GS281125
2016 Toyota Highlander
Limited Platinum AWD
70,088 mi
$25,213
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,024
- Stock #:
- MS260221C
- VIN:
- 5TDGZRBH7MS098720
2021 Toyota Highlander
XLE AWD
88,024 mi
$29,110
- 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:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 22,054
- Stock #:
- X026725XA1
- VIN:
- 5TDFZRBH7NS214141
2022 Toyota Highlander
Platinum AWD
22,054 mi
$43,713
- 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:
- Cypress
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 114,069
- Stock #:
- PBA1190A
- VIN:
- 5TDKDRBH5PS502093
2023 Toyota Highlander
LE AWD
114,069 mi
$25,611
- Year:
- 2012
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Gray
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 5-Speed Automatic
- Mileage:
- 123,355
- Stock #:
- 5353
- VIN:
- 5TDBK3EH9CS110873
2012 Toyota Highlander
SE AWD
123,355 mi
$12,944
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 57,743
- Stock #:
- PJR1505B
- VIN:
- 5TDJZRFH7KS625992
-$687
2019 Toyota Highlander
XLE AWD
57,743 mi
$28,417
$27,730
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 4,027 currently listed for sale and an average price of $39,234.00, 35.6% 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.
88.6% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features an innovative interior design with advanced technology, including a large touchscreen infotainment system and ample cargo space, making it a prime choice for families.
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 68,265
- Stock #:
- 27028I
- VIN:
- 5TDDZRBH9NS191582
2022 Toyota Highlander
Limited AWD
68,265 mi
$31,902
- 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:
- White (Blizzard Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,727
- Stock #:
- XBP8554
- VIN:
- 5TDGZRBH9MS105117
2021 Toyota Highlander
XLE AWD
88,727 mi
$28,331
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 52,433
- Stock #:
- S20248A
- VIN:
- 5TDGZRBH8NS229719
2022 Toyota Highlander
XLE AWD
52,433 mi
$35,008
- 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
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic
- Mileage:
- 111,963
- Stock #:
- 1380
- VIN:
- 5TDZARFH4HS024283
2017 Toyota Highlander
LE
111,963 mi
$17,839
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 17,943
- Stock #:
- CH3332A
- VIN:
- 5TDKDRBH1PS517416
2023 Toyota Highlander
Limited AWD
17,943 mi
$41,908
- 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:
- Predawn Gray Mica
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 226,098
- Stock #:
- 4U26069A
- VIN:
- 5TDDKRFHXFS144142
2015 Toyota Highlander
Limited Platinum AWD
226,098 mi
$13,849
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 45,092
- Stock #:
- H040805XA
- VIN:
- 5TDGZRBH5NS169947
2022 Toyota Highlander
XLE AWD
45,092 mi
$35,013
- Year:
- 2013
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Exterior color:
- CLASSIC SILVER METALLIC
- Interior color:
- ASH
- Transmission:
- Automatic
- Mileage:
- 133,739
- Stock #:
- TA5047A
- VIN:
- 5TDDK3EH1DS259966
2013 Toyota Highlander
Limited V6 AWD
133,739 mi
$16,299
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 81,199
- Stock #:
- PS3791
- VIN:
- 5TDGZRBH6MS103048
2021 Toyota Highlander
XLE AWD
81,199 mi
$28,413
- 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:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 59,716
- Stock #:
- XBP8521
- VIN:
- 5TDGZRBH0LS013005
Sponsored Listing
2020 Toyota Highlander
XLE AWD
59,716 mi
$30,831
FAQs
How much does the Toyota Highlander cost in Madison, WI?
How many Toyota Highlander vehicles in Madison, 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.
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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
Julie W
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.
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 | $53,525 |
| XLE AWD | $45,870 |
| XSE AWD | $47,940 |
| Limited AWD | $50,325 |
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
- Strong Premium for New Models: The 2026 Highlander commands a significant premium at $51,668, approximately 12.6% above its MSRP indicating robust market demand for the latest model.
- Steep Depreciation in Early Years: Older models show substantial depreciation, with the 2019 Highlander priced -$7,301 (−22.9% vs. MSRP), suggesting a steeper decline in value as the vehicle ages.
- Solid Value in Recent Years: The 2021 Highlander offers a balance of price and features at $30,885, about -12.0% vs. MSRP, indicating it could be a strong buy for budget-conscious shoppers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $51,668 | +12.6% |
| 2025 Toyota Highlander | $40,320 | $41,691 | +3.4% |
| 2024 Toyota Highlander | $39,270 | $39,368 | +0.2% |
| 2023 Toyota Highlander | $36,620 | $36,497 | -0.3% |
| 2022 Toyota Highlander | $35,855 | $34,186 | -4.6% |
| 2021 Toyota Highlander | $35,085 | $30,885 | -12.0% |
| 2020 Toyota Highlander | $34,600 | $28,989 | -16.5% |
| 2019 Toyota Highlander | $31,830 | $24,529 | -22.9% |
| 2018 Toyota Highlander | $31,230 | $22,686 | -27.6% |
| 2017 Toyota Highlander | $30,630 | $20,960 | -31.6% |
| 2016 Toyota Highlander | $30,490 | $19,184 | -37.1% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- New York Leads in Pricing: With an average price of $27,033, New York reflects one of the highest demand markets, potentially driven by urban preferences for larger vehicles.
- Dallas Offers Competitive Pricing: Average price in Dallas is $28,080, providing a mid-market option for Highlander shoppers compared to coastal cities.
- Lowest in Chicago: At $25,243, Chicago presents the lowest average price, indicating a potentially more competitive used car market or higher inventory levels.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 702 | $27,033 |
| Los Angeles, CA | 524 | $26,330 |
| Chicago, IL | 355 | $25,243 |
| Dallas, TX | 356 | $28,080 |
| Philadelphia, PA | 284 | $29,612 |
| Houston, TX | 366 | $25,522 |
| Miami, FL | 212 | $29,198 |
| Washington, DC | 445 | $26,763 |
| Atlanta, GA | 336 | $27,023 |
| Boston, MA | 652 | $28,351 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Supply: The XLE AWD trim leads with 3,089 listings, making it a highly available option, likely meeting broad market preferences for features.
- Wide Price Variance Among Trims: The Platinum AWD trim at $53,525 MSRP showcases a premium over other trims, reflecting the added luxury features and technology offered at this level.
- Value Proposition in Mid-Tier Trims: The Limited AWD trim, priced at $50,325 MSRP, represents a strong value for buyers seeking higher-end features without reaching the top-tier pricing.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3,089 | $45,870 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1,177 | $50,325 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 704 | $47,940 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 558 | $53,525 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from June 18, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 4,027 currently listed for sale and an average price of $39,234.00, 35.6% 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.
88.6% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features an innovative interior design with advanced technology, including a large touchscreen infotainment system and ample cargo space, making it a prime choice for families.
Why it stands out
The 2024 Toyota Highlander continues the legacy of its predecessors with its spacious design, reliability, and family-friendly features. With a well-rounded reputation built over generations, this latest model boasts enhanced comfort and advanced safety technologies that appeal to a wide range of consumers. The Highlander not only offers seating for up to eight passengers but also includes optional hybrid variants, presenting an efficient choice for families needing both space and fuel economy. Its smooth ride and quality fit-and-finish resonate well with buyers looking for a dependable midsize SUV.
Other model years to consider
- Average price: $36,398.00
- Good/great deal percentage: 34.1%
- User rating: 4.75 / 5
- Total listings: 4,613
- Average price: $33,757.00
- Good/great deal percentage: 33.9%
- User rating: 4.44 / 5
- Total listings: 4,876
- Average price: $16,191.00
- Good/great deal percentage: 32.2%
- User rating: 4.78 / 5
- Total listings: 1,161
These recommendations are based on CarGurus' proprietary market data from June 15, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$33,246
- User rating4.4444
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$28,325
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,364
- User rating4.8636
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