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Used Toyota Highlander for Sale in

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Chester, MD
Value: 75 miles
Min: 75 milesMax: 75 miles
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Find a Used Toyota Highlander in Chester, MD

TrueCar has 682 used Toyota Highlander models for sale in Chester, MD, including a Toyota Highlander XLE AWD and a Toyota Highlander Platinum AWD. Prices for a used Toyota Highlander in Chester, MD currently range from $2,998 to $111,111, with vehicle mileage ranging from 9 to 436,652. If you wish to buy your used Toyota Highlander online, TrueCar has 1 model available to buy from home, allowing you to purchase your Toyota Highlander remotely and have it delivered directly to your residence in the Chester, MD area. If you prefer to purchase your Toyota Highlander from a dealership near Chester, MD, our TrueCar Certified Dealers have 681 used Toyota Highlander listings available to shop from locally.

Nationwide Toyota Highlander Listings by Year

VehiclePrice FromCertified Pre-OwnedUnder 100k MilesAccident FreeTotal Available
2025 Toyota Highlander$39,77136 listings64 listings61 listings64 listings
2024 Toyota Highlander$27,990191 listings602 listings572 listings603 listings
2023 Toyota Highlander$25,988267 listings1,221 listings1,107 listings1,236 listings
2022 Toyota Highlander$19,991270 listings1,438 listings1,268 listings1,496 listings
2021 Toyota Highlander$18,49581 listings860 listings735 listings947 listings
2020 Toyota Highlander$18,48524 listings334 listings293 listings396 listings
2019 Toyota Highlander$12,9502 listings474 listings422 listings660 listings
2018 Toyota Highlander$13,6260 listings246 listings249 listings405 listings
2017 Toyota Highlander$12,3760 listings153 listings202 listings318 listings
2016 Toyota Highlander$9,9550 listings83 listings149 listings245 listings

Toyota Highlander Owner Reviews

4th Generation Toyota Highlander

2020 - Present
Overall Rating
4.8
10 out of 10
Based on 1,434 Ratings
Performance
4.8
Comfort
4.7
Fuel Efficiency
4.4
Safety Technology
4.7
Features
4.7
All reviews
4.08 out of 10
Performance
4.0
Comfort
4.0
Fuel Efficiency
4.0
Safety Technology
4.0
Features
4.0
Performance
4.0
Comfort
4.0
Fuel Efficiency
4.0
Safety Technology
4.0
Features
4.0
pros
I love how the car drives and handles. It's very roomy and I LOVE the panoramic camera that can also be turned on when moving forward. It makes parking so so easy, it's the BEST!
cons
I would have preferred to have a bench seat in the 2nd row. Unfortunately, in the Hybrid Limited model that is not an option. It would have been had I not gone with the hybrid model. A bench seat would have given me extra seating capacity without taking away space for cargo. In order to accommodate a 5th person, the 3rd row needs to be used. Although the 3rd row is ok for short trip, an adult would not be comfortable in the back for very long and you would lose that cargo space.
Submitted by Lupe H on --- --- ----|2025 Toyota Highlander Hybrid Limited 25th Edition AWD
5.010 out of 10
Performance
5.0
Comfort
5.0
Fuel Efficiency
4.0
Safety Technology
5.0
Features
5.0
pros
Reliability was the #1 factor in my purchase of this vehicle as well as it being a hybrid. I love the gas mileage. I have been driving the hybrids since 2005 when I purchased the Prius, then the Prius V in 2014 and now this vehicle. I like that it has less of an impact on the environment. I love opening the doors with a touch, I like the driver's assist features as well. Using the keyfob to open the trunk, also a favorite. I like the way the car drives. I can't wait for this car to be available as an all electric model.
cons
Visually I feel like I can't see as well in this car as I could in the Prius V and Prius so I rely way more on the driver assist features like the mirror indicator letting me know something is in my blindspot, the warning when a car/pedestrian/cyclist is passing by the rear of my car when I'm ready to back out.
Submitted by Karin E on --- --- ----|2023 Toyota Highlander Hybrid XLE AWD|Purchased on --- --- ----
5.010 out of 10
Performance
5.0
Comfort
5.0
Fuel Efficiency
5.0
Safety Technology
5.0
Features
5.0
pros
Features and handling
cons
4 cylinders
Submitted by Anonymous Author on --- --- ----|2023 Toyota Highlander Hybrid Limited AWD|Purchased on --- --- ----