New & Used 2025 Toyota Highlander for Sale near Windermere, FL

## Summary - With 1,862 currently listed for sale on CarGurus and an **average price of $39,751.00**, 32.7% 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 2025 Toyota Highlander continues to build on its strong reputation for reliability, spaciousness, and impressive safety features. ## Why it stands out The 2025 Toyota Highlander distinguishes itself in the competitive midsize SUV segment by continuing its legacy of reliability and practicality. This year's model maintains the spacious interior layout that accommodates families comfortably, featuring both two-row and three-row configurations. Not only does this make it versatile for family trips, but its respectable fuel efficiency and available hybrid options appeal to eco-conscious buyers. The Highlander's standard safety suite includes Toyota Safety Sense, which offers advanced driver-assistance technologies that enhance safety on the road. While it may not be the most exhilarating drive, its soft suspension and quiet cabin are designed for those who prioritize comfort over sporty handling. Overall, the 2025 model upholds the Highlander's reputation as a solid choice for families seeking a dependable SUV. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $32,571.00 - Good/great deal percentage: 34.3% - User rating: 4.58 / 5 - Total listings: 4,723 - **[2021 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2021-Toyota-Highlander-c30910)** - Average price: $29,325.00 - Good/great deal percentage: 35.2% - User rating: 4.82 / 5 - Total listings: 3,252 - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,229.00 - Good/great deal percentage: 34.8% - User rating: 4.57 / 5 - Total listings: 2,738 This analysis is based on CarGurus' proprietary market data from February 9, 2026, CarGurus experts' opinions, and generative AI.