Used 2021 Toyota Highlander for Sale near Madison, SD

## Summary - With 2,650 currently listed for sale on CarGurus and an **average price of $29,531.00**, 32.1% 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. - **77.4% of 2021 Highlander models on CarGurus are accident free**. - The 2021 Toyota Highlander is one of the best-selling family cars, noted for its safety enhancements, spacious interior, and comfortable ride. ## Why it stands out The 2021 Toyota Highlander is an impressive family SUV that excels in comfort, space, and reliability. It boasts a modern design that catches the eye while incorporating practical features aimed at families. This year, the Highlander benefits from additional standard safety technologies under the Toyota Safety Sense 2.5+ suite, including automatic emergency braking and advanced lane-keeping assist, making it one of the safest choices in its class. Inside, it features an upscale cabin with high-quality materials and ample room for passengers, along with well-placed storage solutions for everyday use. While its V6 engine provides respectable power and smooth operation, it may feel underwhelming to those seeking a sportier driving experience. Nevertheless, the Highlander prioritizes ride comfort and practicality, accommodating up to eight passengers and ideally suited for family outings. Although some drivers noted limitations regarding third-row seating configuration and fuel economy, the Highlander’s overall features and excellent safety ratings make it an appealing choice for many buyers. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $32,739.00 - Good/great deal percentage: 31.5% - User rating: 4.58 / 5 - Total listings: 3,958 - **[2015 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2015-Toyota-Highlander-c24608)** - Average price: $16,640.00 - Good/great deal percentage: 37.8% - User rating: 4.76 / 5 - Total listings: 1,197 - **[2016 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2016-Toyota-Highlander-c25184)** - Average price: $17,934.00 - Good/great deal percentage: 37.6% - User rating: 4.63 / 5 - Total listings: 1,614 This analysis is based on CarGurus' proprietary market data from March 9, 2026, CarGurus experts' opinions, and generative AI.