Used 2025 Toyota Highlander for Sale nearChestertown, NY
80 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 9,246
- Stock #:
- GN2141A
- VIN:
- 5TDKDRBH6RS569174
Sponsored by Genesis of Albany
2024 Toyota Highlander
XLE AWD
9,246 mi
Albany, NY
63 mi away
Fair Deal
$44,152
- 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:
- Moon Dust
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 52,941
- Stock #:
- RS532900T
- VIN:
- 5TDKDRBH0RS532900
New arrival
Sponsored Listing
2024 Toyota Highlander
XLE AWD
52,941 mi
Latham, NY
60 mi away
Fair Deal
$37,670
- 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
Sponsored Listing
2024 Toyota Highlander
XLE AWD
38,581 mi
Saratoga Springs, NY
40 mi away
Good Deal
$36,925
- 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
Saratoga Springs, NY
40 mi away
Good Deal
$36,925
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 3,711
- Stock #:
- 28655529
- VIN:
- 5TDKDRBH8SS593286
2025 Toyota Highlander
Platinum AWD
3,711 mi
Store transfer to Albany, NY
Price includes $799 shipping
Fair Deal
$50,797
- Year:
- 2025
- 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:
- 31,763
- Stock #:
- TP6974
- VIN:
- 5TDKDRBH0SS578202
2025 Toyota Highlander
Platinum AWD
31,763 mi
Home delivery from Milford, MA
Price includes $232 shipping
Great Deal
$47,200
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,207
- Stock #:
- T53100A
- VIN:
- 5TDKDRBH9RS547475
2024 Toyota Highlander
LE AWD
12,207 mi
Pittsfield, MA
87 mi away
Fair Deal
$39,310
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 18,245
- Stock #:
- F10134B
- VIN:
- 5TDKDRBH2RS552050
2024 Toyota Highlander
Platinum AWD
18,245 mi
Westminster, VT
78 mi away
Good Deal
$48,494
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 19,572
- Stock #:
- 577767
- VIN:
- 5TDKDRBHXSS577767
2025 Toyota Highlander
XSE AWD
19,572 mi
Home delivery from Marietta, GA
Price includes $1,768 shipping
Fair Deal
$45,657
- Year:
- 2025
- 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:
- 27,825
- Stock #:
- S576363
- VIN:
- 5TDKDRBH3SS576363
2025 Toyota Highlander
XSE AWD
27,825 mi
Home delivery from Defiance, OH
Price includes $1,120 shipping
Good Deal
$41,692
- 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:
- Silver
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 38,081
- Stock #:
- NV561279
- VIN:
- 5TDKDRBH2RS561279
2024 Toyota Highlander
Limited AWD
38,081 mi
Home delivery from West Park, FL
Price includes $1,271 shipping
Great Deal
$38,190
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 36,848
- Stock #:
- 261228A
- VIN:
- 5TDKDRBH2RS549701
2024 Toyota Highlander
Platinum AWD
36,848 mi
Plattsburgh, NY
73 mi away
Great Deal
$42,429
- Year:
- 2024
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Midnight Black Metal
- Combined gas mileage:
- 25 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 51,861
- Stock #:
- 25052
- VIN:
- 5TDKDRAH9RS527745
2024 Toyota Highlander
XSE FWD
51,861 mi
Home delivery from Marietta, GA
Price includes $1,105 shipping
Fair Deal
$37,604
CarGurus Analysis:
2025 Toyota Highlander
With 1,774 currently listed for sale and an average price of $41,893.00, 37.9% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
91.8% of 2025 Highlander models on CarGurus are accident free.
The 2025 Toyota Highlander continues to impress with its spacious and comfortable interior, excellent safety ratings, and the availability of hybrid models, making it a practical choice for families.
- 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:
- Cypress
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,572
- Stock #:
- TW306092A
- VIN:
- 5TDKDRBH8RS547581
2024 Toyota Highlander
Limited AWD
34,572 mi
Home delivery from Palmetto Bay, FL
Free home delivery
Great Deal
$39,798
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,204
- Stock #:
- F26421A
- VIN:
- 5TDKDRBH0RS560597
2024 Toyota Highlander
XLE AWD
12,204 mi
Home delivery from Charlottesville, VA
Price includes $684 shipping
Fair Deal
$43,674
- 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:
- Brown (Harvest Beige)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 48,579
- Stock #:
- H9722
- VIN:
- 5TDKDRBHXRS538235
2024 Toyota Highlander
XLE AWD
48,579 mi
Home delivery from Downers Grove, IL
Price includes $1,096 shipping
Good Deal
$37,352
- Year:
- 2025
- 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:
- 12,399
- Stock #:
- E4150
- VIN:
- 5TDKDRBH5SS592354
2025 Toyota Highlander
XLE AWD
12,399 mi
Pittsfield, MA
87 mi away
Good Deal
$44,150
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- Front-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 32,533
- Stock #:
- 28734437
- VIN:
- 5TDKDRAHXSS553891
2025 Toyota Highlander
LE FWD
32,533 mi
Store transfer to Albany, NY
Price includes $1,999 shipping
Fair Deal
$34,997
- Year:
- 2025
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 10,042
- Stock #:
- 1TT89976
- VIN:
- 5TDKDRBH2SS589976
2025 Toyota Highlander
XSE AWD
10,042 mi
Home delivery from Greensboro, NC
Price includes $864 shipping
Fair Deal
$46,113
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 58,668
- Stock #:
- 107564
- VIN:
- 5TDKDRBH1RS548135
2024 Toyota Highlander
XLE AWD
58,668 mi
Home delivery from Avenel, NJ
Price includes $424 shipping
Good Deal
$34,823
- 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:
- Celestial Silver Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 55,929
- Stock #:
- PLA534468
- VIN:
- 5TDKDRBH2RS534468
2024 Toyota Highlander
XSE AWD
55,929 mi
Home delivery from New Hudson, MI
Free home delivery
Great Deal
$35,304
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 40,582
- Stock #:
- NG1573
- VIN:
- 5TDKDRBH1RS550855
2024 Toyota Highlander
LE AWD
40,582 mi
Utica, NY
78 mi away
Fair Deal
$34,111
- 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:
- Magnetic Gray Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,207
- Stock #:
- T53100A
- VIN:
- 5TDKDRBH9RS547475
Sponsored Listing
2024 Toyota Highlander
LE AWD
12,207 mi
Pittsfield, MA
87 mi away
Fair Deal
$39,310
CarGurus Analysis: 2025 Toyota Highlander
Summary
With 1,774 currently listed for sale and an average price of $41,893.00, 37.9% of 2025 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
91.8% of 2025 Highlander models on CarGurus are accident free.
The 2025 Toyota Highlander continues to impress with its spacious and comfortable interior, excellent safety ratings, and the availability of hybrid models, making it a practical choice for families.
Why it stands out
The 2025 Toyota Highlander stands out in the crowded midsize SUV market due to its blend of reliability, comfort, and practicality. With a spacious interior that can accommodate up to seven passengers, it is designed for family use, offering ample cargo space and versatile seating configurations. The Highlander is also known for its strong safety record, consistently earning high marks from safety organizations. While it may not be the most exciting vehicle to drive, its smooth ride and quiet cabin make it a pleasant choice for daily commutes and long road trips alike. The introduction of hybrid models further enhances its appeal, providing better fuel efficiency without sacrificing performance. Overall, the Highlander is a well-rounded vehicle that prioritizes comfort and reliability, making it a favorite among families.
Other model years to consider
- Average price: $39,166.00
- Good/great deal percentage: 38.0%
- User rating: 5 / 5
- Total listings: 3,845
- 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
This analysis is based on CarGurus' proprietary market data from July 13, 2026, CarGurus experts' opinions, and generative AI.
2025 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| LE FWD | $40,320 |
| Limited FWD | $47,575 |
| Limited AWD | $49,525 |
| LE AWD | $41,920 |
| Platinum AWD | $52,725 |
| XSE AWD | $47,140 |
| XLE AWD | $45,070 |
| XLE FWD | $43,470 |
2025 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2025 Toyota Highlander prices has changed over time.
See more price trendsAVG Price
$41,816
0.2%
2025 Toyota Highlander
Index Price
$29,111
0.8%
All used vehicles
2025 Toyota Highlander Pricing Analysis
Pricing by Popular US Cities
Market Area: Nationwide
Key Insights
- Highest Price in Dallas: The city of Dallas, TX has the highest average price at $49,132, indicating strong demand and possibly lower inventory.
- Lowest Price in Chicago: Conversely, Chicago, IL offers the lowest average price at $37,758, suggesting a more competitive market or higher inventory levels.
- Inventory Variation: Cities like Boston, MA (167 listings) and New York, NY (120 listings) have significant inventory, which may contribute to more stable pricing around the national average.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Dallas, TX | 108 | $49,132 |
| Philadelphia, PA | 106 | $39,460 |
| New York, NY | 120 | $38,282 |
| Los Angeles, CA | 120 | $38,481 |
| Chicago, IL | 85 | $37,758 |
Pricing by Trim Packages
Key Insights
- XLE AWD Dominates Inventory: The XLE AWD trim leads with 3,145 listings, reflecting strong consumer preference for this configuration.
- Price Range Across Trims: The Limited AWD trim has the highest MSRP at $49,525, while the LE FWD trim is the most affordable at $40,320, indicating a significant price spread of $9,205 between the base and premium trims.
- AWD vs. FWD Demand: AWD trims, such as XLE AWD and Limited AWD, are more prevalent, suggesting a higher demand for all-weather capability.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 3145 | $45,070 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 1387 | $43,470 | FWD | 2.4L 265 hp I4 |
| Limited AWD | 1214 | $49,525 | AWD | 2.4L 265 hp I4 |
| LE FWD | 737 | $40,320 | FWD | 2.4L 265 hp I4 |
| XSE AWD | 703 | $47,140 | AWD | 2.4L 265 hp I4 |
| LE AWD | 684 | $41,920 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 549 | $52,725 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 368 | $47,575 | FWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Toyota Highlander is priced at $52,195, which is approximately 12.5% above its MSRP, indicating strong demand for the latest model.
- Depreciation Trends: The 2019 Highlander shows a significant depreciation of -23.8% compared to its original MSRP, reflecting typical market behavior for older models.
- Best Value Years: The 2022 Highlander is priced at $33,752, only -6.1% below its MSRP, making it a compelling option for buyers seeking value without sacrificing recency.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 | $46,270 | $52,195 | +12.5% |
| 2024 | $39,270 | $39,217 | -0.1% |
| 2023 | $36,620 | $36,118 | -1.4% |
| 2022 | $35,855 | $33,752 | -6.1% |
| 2021 | $35,085 | $30,794 | -12.2% |
| 2020 | $34,600 | $28,502 | -17.7% |
| 2019 | $31,830 | $24,243 | -23.8% |
| 2018 | $31,230 | $22,413 | -28.2% |
| 2017 | $30,630 | $21,000 | -31.7% |
| 2016 | $30,490 | $18,750 | -38.5% |
| 2015 | $29,765 | $17,256 | -42.3% |
These recommendations are based on CarGurus' proprietary market data from July 16, 2026, CarGurus experts' opinions, and generative AI.
FAQs
How much does the 2025 Toyota Highlander cost in Chestertown, NY?
The average 2025 Toyota Highlander costs about $41,816.35. The average price has increased by 5.5% since last year. The 54 for sale near Chestertown, NY on CarGurus, range from $26,670 to $53,782 in price.
How many 2025 Toyota Highlander vehicles in Chestertown, NY have no reported accidents or damage?
48 out of 54 for sale near Chestertown, NY have no reported accidents or damage.
What is the fuel economy of the 2025 Toyota Highlander?
Depending on the engine and options, the 2025 Toyota Highlander gets between 24 and 25 MPG (or EV battery range).
What fuel types are available?
Gasoline engines are available.
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