Used 2021 Toyota Highlander for Sale near Key West, FL

Summary

• With 4,417 currently listed for sale on CarGurus and an average price of $30,215.80, 35.7% of 2021 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
• Favorably reviewed: Owners rated the 2021 Toyota Highlander 4.8 / 5 stars and CarGurus experts gave it an 7.5 / 10.
• 79.4% of 2021 Highlander models on CarGurus are accident free.
• The 2021 Toyota Highlander combined spaciousness and comfort with improved standard safety features, making it a strong contender in the competitive three-row SUV market.

Why it stands out

The 2021 Toyota Highlander stood out in the competitive three-row SUV market with its impressive ride quality and spacious interior, making it a comfortable choice for families. It also included advanced safety technology as standard equipment, enhancing its appeal to safety-conscious buyers. While some may have found its styling uninspired and base engine performance modest, the Highlander's strong name recognition and reliability continued to attract consumers.

Other model years to consider

• 2022 Toyota Highlander: This year offers $33,572.41 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,308 listings.
• 2023 Toyota Highlander: This year offers $35,244.49 average price, 35% good/great deals, 4.4/5 user rating, 6,084 listings.
• 2019 Toyota Highlander: This year offers $23,940.47 average price, 36% good/great deals, 4.6/5 user rating, 3,041 listings.

This analysis is based on CarGurus' proprietary market data from December 16, 2025, CarGurus experts' opinions, and generative AI.