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

## Summary - With 1,805 currently listed for sale on CarGurus and an **average price of $39,916.00**, 34.0% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **93.6% of 2025 Highlander models on CarGurus are accident-free**. - The notable features of the 2025 Toyota Highlander include its spacious interior, enhanced safety features, and strong reliability. ## Why it stands out The 2025 Toyota Highlander continues to build on the strengths of its predecessors with a reputation for reliability and spaciousness, making it an excellent option for families. This model year offers a blend of comfort and versatility, featuring an innovative layout that supports up to seven passengers with an optional third row. Additionally, its unibody construction enhances fuel efficiency and handling compared to traditional body-on-frame SUVs. The Highlander's great safety ratings and numerous up-to-date safety technology make it particularly appealing for those prioritizing peace of mind during their travels. While it may not offer an exhilarating driving experience, its soft suspension contributes to a smooth and comfortable ride, which has been favored by many buyers. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $32,527.00 - Good/great deal percentage: 34.1% - User rating: 4.58 / 5 - Total listings: 4,730 - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-c30910)** - Average price: $29,284.00 - Good/great deal percentage: 34.7% - User rating: 4.82 / 5 - Total listings: 3,255 - **[2020 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2020-Toyota-Highlander-c29164)** - Average price: $27,092.00 - Good/great deal percentage: 35.9% - User rating: 4.48 / 5 - Total listings: 2,975 This analysis is based on CarGurus' proprietary market data from February 10, 2026, CarGurus experts' opinions, and generative AI.