Used 2021 Toyota Highlander for Sale near Reedsburg, WI

## Summary - With 3,016 currently listed for sale on CarGurus and an **average price of $29,272.00**, 33.6% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2021 Toyota Highlander 4.82 / 5 stars and CarGurus experts gave it an 7.5 / 10. - **78.3% of 2021 Highlander models on CarGurus are accident free**. - The 2021 Toyota Highlander stands out for its blend of safety features, comfort, and a spacious interior, making it an ideal choice for families. ## Why it stands out The 2021 Toyota Highlander continues to solidify its reputation as a top-selling family vehicle, now entering its 20th year of production. This model year brings notable safety feature upgrades, courtesy of Toyota Safety Sense 2.5+, which includes advanced technologies such as automatic emergency braking and intersection support, ensuring peace of mind for families on the road. Many users praise the 2021 Highlander for its comfort and spaciousness, while the high-quality interior adds to the overall positive driving experience. Despite its sedate performance, the Highlander excels in delivering a smooth ride and well-balanced comfort, which are essential traits for family-oriented shoppers. While some may find the base engine uninspiring and the technology somewhat outdated, the overall quality and reliability further enhance its appeal. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $32,524.00 - Good/great deal percentage: 32.8% - User rating: 4.58 / 5 - Total listings: 4,445 - **[2015 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2015-Toyota-Highlander-c24608)** - Average price: $16,541.00 - Good/great deal percentage: 39.7% - User rating: 4.76 / 5 - Total listings: 1,292 - **[2016 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2016-Toyota-Highlander-c25184)** - Average price: $18,119.00 - Good/great deal percentage: 38.4% - User rating: 4.63 / 5 - Total listings: 1,759 This analysis is based on CarGurus' proprietary market data from February 23, 2026, CarGurus experts' opinions, and generative AI.