Used 2021 Toyota Highlander for Sale nearMilwaukee, WI
185 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 115,685
- Stock #:
- MS149022
- VIN:
- 5TDFZRBH4MS149022
Sponsored by Zeigler Toyota of Racine
2021 Toyota Highlander
Platinum AWD
115,685 mi
$31,436
- 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:
- Blueprint
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 43,941
- Stock #:
- P22921
- VIN:
- 5TDGZRBH5NS228785
Sponsored Listing
2022 Toyota Highlander
XLE AWD
43,941 mi
$35,489
- 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:
- 37,261
- Stock #:
- T16911B
- VIN:
- 5TDGZRBH0NS208993
Sponsored Listing
2022 Toyota Highlander
XLE AWD
37,261 mi
$36,185
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 89,930
- Stock #:
- 29142
- VIN:
- 5TDCZRBHXMS530280
-$700
2021 Toyota Highlander
L AWD
89,930 mi
$24,158
$23,458
- 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
-$998
2022 Toyota Highlander
XLE AWD
56,116 mi
$35,507
$34,509
- 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:
- Red (Ruby Flare Pearl)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 17,927
- VIN:
- 5TDGZRBH8NS594174
2022 Toyota Highlander
XLE AWD
17,927 mi
$39,675
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 27,202
- Stock #:
- 27866JF
- VIN:
- 5TDGZRBH2MS065009
2021 Toyota Highlander
XLE AWD
27,202 mi
$33,726
- 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:
- Red
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 8-Speed Automatic
- Mileage:
- 88,662
- Stock #:
- WYC-562432
- VIN:
- 5TDDZRBH5NS562432
2022 Toyota Highlander
Limited AWD
88,662 mi
$32,999
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 65,670
- Stock #:
- 9D0439A
- VIN:
- 5TDLZRBH4MS065320
2021 Toyota Highlander
XSE AWD
65,670 mi
$33,194
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,952
- Stock #:
- 912
- VIN:
- 5TDJZRAH3MS048517
2021 Toyota Highlander
XSE FWD
51,952 mi
$33,806
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 64,268
- Stock #:
- TPP3174
- VIN:
- 5TDLZRBH4NS183675
2022 Toyota Highlander
XSE AWD
64,268 mi
$34,796
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 85,045
- Stock #:
- 06X1457A
- VIN:
- 5TDHZRBH5LS034758
2020 Toyota Highlander
XLE AWD
85,045 mi
$29,176
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 79,720
- Stock #:
- 056928
- VIN:
- 5TDJZRBH0MS056928
2021 Toyota Highlander
XSE AWD
79,720 mi
$32,247
CarGurus Analysis:
2021 Toyota Highlander
With 181 currently listed for sale near Milwaukee, WI and an average price of $32,470.00, 35.4% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it a top 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:
- Pearl
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 60,289
- Stock #:
- 1052552
- VIN:
- 5TDGZRBH2NS578083
2022 Toyota Highlander
XLE AWD
60,289 mi
$33,932
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 70,513
- Stock #:
- 071387
- VIN:
- 5TDLZRAH9MS071387
2021 Toyota Highlander
XSE FWD
70,513 mi
$32,050
- 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:
- Red
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 18,029
- Stock #:
- 163648
- VIN:
- 5TDBZRBH5LS509394
2020 Toyota Highlander
LE AWD
18,029 mi
$32,285
- 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:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,677
- Stock #:
- H168006
- VIN:
- 5TDFZRBH0NS168006
2022 Toyota Highlander
Platinum AWD
35,677 mi
$39,771
- 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:
- Light Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 65,826
- Stock #:
- l085625
- VIN:
- 5TDZZRAH0MS085625
2021 Toyota Highlander
LE FWD
65,826 mi
$28,056
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 74,723
- Stock #:
- 535351
- VIN:
- 5TDGZRAH6MS535351
2021 Toyota Highlander
XLE FWD
74,723 mi
$29,950
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 70,694
- Stock #:
- 103912A
- VIN:
- 5TDGZRBH2NS234866
2022 Toyota Highlander
XLE AWD
70,694 mi
$33,206
- 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:
- Red
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 58,825
- Stock #:
- 520713
- VIN:
- 5TDBZRBH6LS520713
2020 Toyota Highlander
LE AWD
58,825 mi
$25,094
- 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:
- Gray
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 70,406
- Stock #:
- 527557
- VIN:
- 5TDHZRBH4MS527557
2021 Toyota Highlander
XLE AWD
70,406 mi
$28,720
- 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:
- Blueprint
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,668
- Stock #:
- 70661B
- VIN:
- 5TDGZRBH0NS188552
Sponsored Listing
2022 Toyota Highlander
XLE AWD
103,668 mi
$30,093
CarGurus Analysis: 2021 Toyota Highlander
overall
Summary
With 181 currently listed for sale near Milwaukee, WI and an average price of $32,470.00, 35.4% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.86 / 5 stars.
100.0% of 2021 Highlander models on CarGurus are accident free.
The 2021 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it a top choice for families.
Why it stands out
The 2021 Toyota Highlander stands out in the competitive three-row SUV market due to its blend of comfort, reliability, and advanced safety features. With a powerful 3.5-liter V6 engine producing 295 horsepower, it offers a smooth and predictable driving experience, ideal for family outings. The Highlander has been praised for its spacious interior, which includes ample legroom in the second row and a well-designed cargo area that can expand significantly when the third row is folded down. Additionally, the introduction of the XSE trim adds a sportier aesthetic without compromising on comfort. Safety is a key focus, with the Highlander equipped with Toyota Safety Sense 2.5+, which includes features like automatic emergency braking and adaptive cruise control. While some may find the styling uninspired and the base engine underwhelming, the overall package of the Highlander makes it a compelling choice for buyers seeking a reliable family vehicle.
Other model years to consider
- Average price: $37,710.00
- Good/great deal percentage: 64.2%
- User rating: 5 / 5
- Total listings: 137
- Average price: $16,238.00
- Good/great deal percentage: 29.7%
- User rating: 4.93 / 5
- Total listings: 118
- Average price: $23,150.00
- Good/great deal percentage: 34.1%
- User rating: 4.76 / 5
- Total listings: 179
This analysis is based on CarGurus' proprietary market data from July 7, 2026, CarGurus experts' opinions, and generative AI.
4.9 Overall rating
Filter by rating
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.
Tony T
Reviewed a 2021 Toyota Highlander on Jul 5, 2022
Love this 2021 Highlander SXE model, got all the bells and whistles. No complaints. Can’t go wrong with Toyota. Out of the 20 SUV with 5000 lbs towing, this one is top IMO.
Melissa C
Reviewed a 2021 Toyota Highlander on May 6, 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.
Frederick and Mariah P
Reviewed a 2021 Toyota Platinum AWD on Mar 5, 2023
Absolutely love the upgraded features of this car. The panoramic sunroof is stunning, the infotainment screen is huge and easy to operate, the seats are insanely comfortable, and the ride is so smooth and surprisingly quiet on the inside. We haven’t had the car for long but we are absolutely loving it so far. We are so glad that we decided to go with the platinum trim!
2021 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE AWD | $38,885 |
| LE FWD | $37,285 |
| XSE FWD | $41,680 |
| Limited AWD | $45,990 |
| XSE AWD | $43,630 |
| Platinum AWD | $49,190 |
| XLE FWD | $40,085 |
| XLE AWD | $41,685 |
2021 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2021 Toyota Highlander prices has changed over time.
See more price trends2021 Toyota Highlander Pricing Analysis: Milwaukee, WI Market Report
Pricing by Nearby Locations
Market Area: Milwaukee, WI
Key Insights
- Highest Prices in Madison: The city of Madison, WI has the highest average price at $33,990, indicating strong demand or limited supply in that area.
- Lowest Prices in Appleton: Appleton, WI offers the lowest average price at $30,489, suggesting a more price-sensitive market or higher inventory turnover.
- Inventory Variation: Cities like Kenosha (218 listings) and Palatine (224 listings) show a healthy inventory, with average prices around $32,041 and $31,399, respectively, indicating stable pricing dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Madison, WI | 177 | $33,990 |
| Kenosha, WI | 218 | $32,041 |
| Fond du Lac, WI | 172 | $31,724 |
| Palatine, IL | 224 | $31,399 |
| Janesville, WI | 183 | $31,490 |
| Rockford, IL | 183 | $31,939 |
| Chicago, IL | 223 | $31,495 |
| Muskegon, MI | 172 | $30,495 |
| Appleton, WI | 161 | $30,489 |
Pricing by Trim Packages
Key Insights
- AWD Trims Lead Inventory: The XLE AWD trim is the most common with 187 listings, reflecting strong demand for all-wheel drive options.
- Price Range Across Trims: The Limited AWD trim has the highest MSRP at $45,990, indicating a premium offering with additional features.
- Value in Base Trims: The LE FWD trim, with an MSRP of $37,285, provides a more budget-friendly option while still offering essential features.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 187 | $41,685 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 87 | $45,990 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 54 | $40,085 | FWD | 3.5L 295 hp V6 |
| LE FWD | 34 | $37,285 | FWD | 3.5L 295 hp V6 |
| LE AWD | 44 | $38,885 | AWD | 3.5L 295 hp V6 |
| XSE AWD | 45 | $43,630 | AWD | 3.5L 295 hp V6 |
| Platinum AWD | 39 | $49,190 | AWD | 3.5L 295 hp V6 |
| Limited FWD | 19 | $44,040 | FWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- Newer Models Retain Value: The 2025 Highlander is priced at $38,382, which is about -2.3% below MSRP, indicating strong demand for the latest model.
- Significant Depreciation for Older Models: The 2019 Highlander shows a steep decline, priced at $22,160, which is -30.2% from its original MSRP.
- Best Value in Mid-Range Years: The 2022 Highlander is priced at $33,870, reflecting a modest depreciation of -5.5%, making it a potentially attractive option for buyers.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2025 | $40,320 | $38,382 | -2.3% |
| 2024 | $39,270 | $39,194 | -0.2% |
| 2023 | $36,620 | $36,268 | -1.0% |
| 2022 | $35,855 | $33,870 | -5.5% |
| 2020 | $34,600 | $30,971 | -10.5% |
| 2019 | $31,830 | $22,160 | -30.2% |
| 2018 | $31,230 | $20,749 | -33.6% |
| 2017 | $30,630 | $18,497 | -39.8% |
| 2016 | $30,490 | $13,714 | -55.1% |
| 2015 | $29,765 | $17,944 | -39.7% |
These recommendations are based on CarGurus' proprietary market data from July 9, 2026, CarGurus experts' opinions, and generative AI.
FAQs
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