New & Used 2025 Toyota Highlander for Sale near Winchester, MA

## Summary - With 1,899 currently listed for sale on CarGurus and an **average price of $40,427.00**, 28.7% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **93.4% of 2025 Highlander models on CarGurus are accident free**. ## Why it stands out The 2025 Toyota Highlander continues the brand's tradition of offering a practical and spacious midsize SUV that appeals to family-oriented buyers. This year, the Highlander emphasizes utility with a flexible interior, enabling maximum cargo space of up to 84.3 cubic feet when the third-row seats are folded down. Additionally, the model maintains Toyota's commitment to safety, with features like Toyota Safety Sense, which includes advanced safety technologies. While the Highlander may not be the most thrilling SUV to drive due to its soft suspension and lack of powerful engine options, its reputation for reliability and comfort makes it a solid choice for families needing a capable vehicle for daily life and weekend getaways. ## Other model years to consider - **[2023 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2023-Toyota-Highlander-c32651)** - Average price: $34,415.00 - Good/great deal percentage: 25.4% - User rating: 4.36 / 5 - Total listings: 4,656 - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $32,499.00 - Good/great deal percentage: 25.1% - User rating: 4.58 / 5 - Total listings: 4,590 - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-c30910)** - Average price: $29,233.00 - Good/great deal percentage: 26.0% - User rating: 4.82 / 5 - Total listings: 3,161 This analysis is based on CarGurus' proprietary market data from February 16, 2026, CarGurus experts' opinions, and generative AI.