Used Toyota Highlander for Sale nearChestertown, NY
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 77,305
- Stock #:
- NG1695
- VIN:
- 5TDKDRBH3PS033098
Sponsored by New Generation Cars
2023 Toyota Highlander
LE AWD
77,305 mi
$30,796
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Cockpit Red
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,343
- Stock #:
- PS514138TL
- VIN:
- 5TDKDRBH6PS514138
Sponsored Listing
2023 Toyota Highlander
XSE AWD
35,343 mi
$40,170
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 95,038
- Stock #:
- 48251A
- VIN:
- 5TDBZRFH3JS811256
-$512
Sponsored Listing
2018 Toyota Highlander
LE AWD
95,038 mi
$19,999
$19,487
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 96,837
- Stock #:
- 70022704
- VIN:
- 5TDGZRAH0NS111875
2022 Toyota Highlander
XLE FWD
96,837 mi
$28,297
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Blueprint
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,873
- Stock #:
- 26022A
- VIN:
- 5TDGZRBH0NS244635
2022 Toyota Highlander
XLE AWD
75,873 mi
$28,998
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 78,538
- Stock #:
- H30547A
- VIN:
- 5TDGZRBH2LS051612
2020 Toyota Highlander
XLE AWD
78,538 mi
$28,449
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Black
- Combined gas mileage:
- 21 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 79,101
- Stock #:
- FS376
- VIN:
- 5TDBKRFH3GS239280
2016 Toyota Highlander
LE AWD
79,101 mi
$20,171
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 62,854
- Stock #:
- 26DP030
- VIN:
- 5TDBZRBH1NS574083
2022 Toyota Highlander
LE AWD
62,854 mi
$29,594
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Moon Dust
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,643
- Stock #:
- 110507
- VIN:
- 5TDGZRBH1MS122591
-$825
2021 Toyota Highlander
XLE AWD
49,643 mi
$32,042
$31,217
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 76,610
- Stock #:
- S26309A
- VIN:
- 5TDHZRBH6MS126995
2021 Toyota Highlander
XLE AWD
76,610 mi
$28,698
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 115,599
- Stock #:
- 17525A
- VIN:
- 5TDDZRFH9JS895978
2018 Toyota Highlander
Limited Platinum AWD
115,599 mi
$22,997
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 38,581
- Stock #:
- 572488
- VIN:
- 5TDKDRBH0RS572488
2024 Toyota Highlander
XLE AWD
38,581 mi
$36,925
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Almond
- Transmission:
- 8-Speed Automatic
- Mileage:
- 103,298
- Stock #:
- D706559A
- VIN:
- 5TDJZRFH4KS706559
2019 Toyota Highlander
XLE AWD
103,298 mi
$23,577
Recommended model year:
2024 Toyota Highlander
Shop 2024 Toyota Highlander »With 3,845 currently listed for sale and an average price of $39,166.00, 38.0% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.0% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
- Year:
- 2020
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 47,759
- Stock #:
- 22591A
- VIN:
- 5TDFZRBH7LS054257
2020 Toyota Highlander
Platinum AWD
47,759 mi
$33,076
- Year:
- 2021
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 56,585
- Stock #:
- 093409T
- VIN:
- 5TDGZRBH4MS093409
-$1,000
2021 Toyota Highlander
XLE AWD
56,585 mi
$32,069
$31,069
- Year:
- 2017
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Pearl White
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 124,898
- Stock #:
- 9166T
- VIN:
- 5TDJZRFH6HS419166
-$423
2017 Toyota Highlander
XLE AWD
124,898 mi
$19,125
$18,702
- Year:
- 2016
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 270 hp 3.5L V6
- Exterior color:
- Silver Sky Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 77,759
- Stock #:
- S2005A
- VIN:
- 5TDBKRFH1GS287277
2016 Toyota Highlander
LE Plus AWD
77,759 mi
$21,504
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Predawn Gray Mica
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Ash
- Transmission:
- 8-Speed Automatic
- Mileage:
- 75,507
- Stock #:
- T16311A
- VIN:
- 5TDJZRFH2KS606654
2019 Toyota Highlander
XLE AWD
75,507 mi
$26,697
- Year:
- 2023
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 73,021
- Stock #:
- SV3258
- VIN:
- 5TDKDRBH8PS523942
-$800
2023 Toyota Highlander
XLE AWD
73,021 mi
$33,395
$32,595
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 90,298
- Stock #:
- 260845A
- VIN:
- 5TDGZRBH3NS218675
2022 Toyota Highlander
XLE AWD
90,298 mi
$29,158
- Year:
- 2022
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Midnight Black Metallic
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 84,186
- Stock #:
- M2607A
- VIN:
- 5TDBZRBH2NS566588
-$2,258
2022 Toyota Highlander
LE AWD
84,186 mi
$27,245
$25,386
- Year:
- 2019
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- Red
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Interior color:
- Acv
- Transmission:
- Automatic
- Mileage:
- 88,786
- Stock #:
- 2992
- VIN:
- 5TDJZRFH8KS730914
2019 Toyota Highlander
SE AWD
88,786 mi
$22,900
- Year:
- 2018
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 295 hp 3.5L V6
- Exterior color:
- White (Blizzard Pearl)
- Combined gas mileage:
- 22 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 104,630
- Stock #:
- 47751A
- VIN:
- 5TDJZRFH1JS527264
Sponsored Listing
2018 Toyota Highlander
XLE AWD
104,630 mi
$22,699
FAQs
How much does the Toyota Highlander cost in Chestertown, NY?
How many Toyota Highlander vehicles in Chestertown, NY have no reported accidents or damage?
What fuel types are available?
4.7 Overall rating
Customers say
Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.
AI generated from the text of customer reviews.
Filter by year
Filter by rating
What people say
Anonymous
Reviewed a 2024 Toyota XLE AWD on Dec 10, 2025
The 2024 Toyota Highlander XLE offers insane cabin room, comfort and luxury feel. The chassis makes an absolute smooth, dream and comfortable ride. Cabin rear chairs makes four adults feel like your in a Sequoia with room. Absolute beautiful and enjoyable ride and purchase
Julie W
Reviewed a 2021 Toyota Highlander on Jul 20, 2024
I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.
Erdem S
Reviewed a 2022 Toyota Limited FWD on Jul 15, 2026
Outstanding reliability record. One of the most dependable midsize SUVs ever built. Excellent resale value.
Luong S
Reviewed a 2012 Toyota Base on Apr 26, 2026
This car's features are very good and have great value the only missing is it has only one key.
Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Platinum AWD | $53,925 |
| XLE AWD | $46,270 |
| XSE AWD | $48,340 |
| Limited AWD | $50,725 |
Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of Toyota Highlander prices has changed over time.
See more price trendsToyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Toyota Highlander is priced at $52,195, reflecting a 12.6% increase over its MSRP, indicating strong demand for the latest model.
- Steep Depreciation for Older Models: The 2016 Highlander shows the most significant depreciation at -38.6% compared to its original MSRP, highlighting the rapid value loss in older vehicles.
- Best Value Year: The 2021 model is currently priced at $30,794, representing a -12.8% depreciation, making it a potentially attractive option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $52,195 | +12.6% |
| 2025 Toyota Highlander | $40,320 | $41,395 | +2.7% |
| 2024 Toyota Highlander | $39,270 | $39,217 | -0.1% |
| 2023 Toyota Highlander | $36,620 | $36,118 | -1.4% |
| 2022 Toyota Highlander | $35,855 | $33,752 | -5.9% |
| 2021 Toyota Highlander | $35,085 | $30,794 | -12.8% |
| 2020 Toyota Highlander | $34,600 | $28,502 | -17.7% |
| 2019 Toyota Highlander | $31,830 | $24,243 | -23.9% |
| 2018 Toyota Highlander | $31,230 | $22,413 | -28.3% |
| 2017 Toyota Highlander | $30,630 | $21,000 | -31.7% |
| 2016 Toyota Highlander | $30,490 | $18,750 | -38.6% |
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Prices in New York: The New York, NY market commands the highest average price at $26,343, likely due to higher demand and lower inventory.
- Lowest Prices in Chicago: Chicago, IL offers the most competitive pricing at $24,441, suggesting a more price-sensitive market with higher inventory levels.
- Price Variation Across Cities: The average prices range from $24,441 in Chicago to $28,094 in Philadelphia, indicating regional differences in demand and supply dynamics.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| New York, NY | 623 | $26,343 |
| Los Angeles, CA | 512 | $25,822 |
| Chicago, IL | 336 | $24,441 |
| Dallas, TX | 346 | $27,231 |
| Philadelphia, PA | 284 | $28,094 |
| Houston, TX | 352 | $25,014 |
| Miami, FL | 206 | $29,375 |
| Washington, DC | 457 | $26,857 |
| Atlanta, GA | 335 | $26,920 |
| Boston, MA | 603 | $27,856 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Inventory: The XLE AWD trim leads with 3,148 listings, indicating strong consumer preference for this configuration.
- Premium Pricing for Limited AWD: The Limited AWD trim, priced at $50,725, reflects a significant markup due to its luxury features, appealing to buyers seeking higher-end options.
- Consistent Features Across Trims: All trims offer similar popular features, such as backup cameras and adaptive cruise control, suggesting that buyers can expect a high level of standard equipment regardless of the trim chosen.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3148 | $46,270 | AWD | 2.4L 265 hp I4 |
| Limited AWD | 1212 | $50,725 | AWD | 2.4L 265 hp I4 |
| XSE AWD | 703 | $48,340 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 549 | $53,925 | AWD | 2.4L 265 hp I4 |
These recommendations are based on CarGurus' proprietary market data from July 16, 2026, CarGurus experts' opinions, and generative AI.
CarGurus recommends the 2024 Toyota Highlander
Summary
With 3,845 currently listed for sale and an average price of $39,166.00, 38.0% of 2024 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2024 Toyota Highlander 5 / 5 stars.
88.0% of 2024 Highlander models on CarGurus are accident free.
The 2024 Toyota Highlander features a spacious interior, advanced safety technology, and a smooth ride, making it an excellent choice for families.
Why it stands out
The 2024 Toyota Highlander continues to build on its reputation as a reliable and family-friendly SUV. With its spacious interior and comfortable seating for up to eight passengers, it is designed to accommodate families and their gear with ease. The Highlander is equipped with a suite of advanced safety features, including Toyota Safety Sense, which enhances driver confidence. Its smooth ride and refined handling make it a pleasure to drive, while the availability of hybrid models offers excellent fuel efficiency. Overall, the Highlander is a well-rounded vehicle that appeals to buyers looking for practicality and reliability in a midsize SUV.
Other model years to consider
- Average price: $36,159.00
- Good/great deal percentage: 37.2%
- User rating: 4.75 / 5
- Total listings: 4,496
- Average price: $30,445.00
- Good/great deal percentage: 36.1%
- User rating: 4.86 / 5
- Total listings: 3,248
- Average price: $33,455.00
- Good/great deal percentage: 36.6%
- User rating: 4.44 / 5
- Total listings: 4,837
These recommendations are based on CarGurus' proprietary market data from July 13, 2026, CarGurus experts' opinions, and generative AI.
Recent expert test drives
2022 Toyota Highlander
- Expert review8/10
- MSRP$35,855-$49,960
- Avg. price$32,991
- User rating4.5
2020 Toyota Highlander
- Expert review8/10
- MSRP$34,600-$48,800
- Avg. price$27,869
- User rating4.6
2021 Toyota Highlander
- Expert review8/10
- MSRP$35,085-$49,190
- Avg. price$30,211
- User rating4.8636
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