Used 2021 Toyota Highlander for Sale near Pound Ridge, NY

## Summary - With 2,559 currently listed for sale and an **average price of $29,622.00**, 30.3% 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. - **77.8% of 2021 Highlander models on CarGurus are accident free**. - The 2021 Toyota Highlander offers a spacious interior, advanced safety features, and a comfortable ride, making it a strong contender in the family SUV market. ## Why it stands out The 2021 Toyota Highlander distinguishes itself in the crowded three-row SUV category through its blend of comfort, reliability, and family-friendly features. With a robust 3.5-liter V6 engine that delivers 295 horsepower, the Highlander strikes a solid balance between power and fuel efficiency, though it may not be the fastest option in its class. The model also boasts a refined interior with high-quality materials and a thoughtful layout that prioritizes passenger comfort and convenience. Toyota has added various safety technologies as standard equipment for 2021, including Toyota Safety Sense 2.5+, which enhances the already impressive safety profile of this vehicle. The Highlander's smooth ride is further complemented by an impressive range of tech features, making it a practical choice for families. While some reviews note its uninspired styling and an engine that could be more engaging, the overall package supports its reputation as a reliable family SUV. ## Other model years to consider - **[2022 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2022-Toyota-Highlander-c31996)** - Average price: $33,089.00 - Good/great deal percentage: 30.5% - User rating: 4.58 / 5 - Total listings: 3,898 - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,467.00 - Good/great deal percentage: 35.0% - User rating: 4.57 / 5 - Total listings: 2,167 - **[2023 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2023-Toyota-Highlander-c32651)** - Average price: $35,417.00 - Good/great deal percentage: 31.5% - User rating: 4.36 / 5 - Total listings: 3,967 This analysis is based on CarGurus' proprietary market data from March 23, 2026, CarGurus experts' opinions, and generative AI.