Used Toyota Highlander for Sale nearChesterfield, MA
22 vehicles found
- Year:
- 2026
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2,548
- Stock #:
- 260581A
- VIN:
- 5TDKDRBH5TS595563
2026 Toyota Highlander
Platinum AWD
2,548 mi
Hartford, CT
42 mi away
Great Deal
$52,129
- Year:
- 2026
- 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
- Transmission:
- Automatic
- Mileage:
- 8,444
- Stock #:
- 29008088
- VIN:
- 5TDKDRBH8TS597906
2026 Toyota Highlander
XLE AWD
8,444 mi
Store transfer to Hartford, CT
Price includes $799 shipping
Fair Deal
$47,797
- Year:
- 2026
- 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:
- Black
- Transmission:
- Automatic
- Mileage:
- 6,867
- Stock #:
- 28062597
- VIN:
- 5TDKDRBH0TS595339
2026 Toyota Highlander
Limited AWD
6,867 mi
Store transfer to Hartford, CT
Price includes $1,399 shipping
Fair Deal
$51,397
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Red
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 4,495
- Stock #:
- 27152554
- VIN:
- 5TDKDRBH2TS603957
2026 Toyota Highlander
Platinum AWD
4,495 mi
Store transfer to Hartford, CT
Price includes $1,999 shipping
Fair Deal
$53,997
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Red
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 10
- Stock #:
- TJT686
- VIN:
- 5TDKDRBH7TS610709
2026 Toyota Highlander
XLE AWD
New car
Home delivery from Laconia, NH
Price includes $216 shipping
New car
TSRP $49,693
$46,409
- Year:
- 2026
- 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:
- Brown
- Transmission:
- Automatic
- Mileage:
- 10
- Stock #:
- TJT790
- VIN:
- 5TDKDRBH3TS612666
New arrival
2026 Toyota Highlander
Platinum AWD
New car
Home delivery from Laconia, NH
Price includes $216 shipping
New car
TSRP $57,197
$57,413
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Gray
- Fuel type:
- Gasoline
- Interior color:
- Gray (GRAPHITE SOFTEX -TRIMMED)
- Transmission:
- Automatic
- Mileage:
- 3
- Stock #:
- 48332
- VIN:
- 5TDKDRBH5TS612040
New arrival
2026 Toyota Highlander
New car
Home delivery from St Albans, VT
Price includes $168 shipping
New car
TSRP $49,063
$49,730
- Year:
- 2026
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 283
- Stock #:
- 267035
- VIN:
- 5TDKDRBH7TS611021
2026 Toyota Highlander
XSE AWD
New car
Hartford, CT
42 mi away
New car
TSRP $52,943
$52,443
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 0
- Stock #:
- TS27J530
- VIN:
- 5TDKDRBH3TS27J530
2026 Toyota Highlander
Platinum AWD
New car
West Springfield, MA
20 mi away
New car
TSRP $55,998
$56,782
- Year:
- 2026
- 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:
- 8-Speed Automatic
- Mileage:
- 0
- Stock #:
- TT261561
- VIN:
- 5TDKDRBH7TS30J516
2026 Toyota Highlander
Limited AWD
New car
Manchester, CT
43 mi away
New car
TSRP $55,247
$55,946
- Year:
- 2026
- 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
- Transmission:
- Automatic
- Mileage:
- 0
- Stock #:
- AT1292
- VIN:
- 5TDKDRBH8TS612484
2026 Toyota Highlander
Platinum AWD
New car
West Springfield, MA
20 mi away
New car
TSRP $56,073
$56,857
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2
- Stock #:
- W269344
- VIN:
- 5TDKDRBH1TS610513
2026 Toyota Highlander
Platinum AWD
New car
Home delivery from Westbury, NY
Price includes $750 shipping
New car
$60,045
- Year:
- 2026
- 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
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Glazed Caramel
- Transmission:
- 8-Speed Automatic
- Mileage:
- 4,978
- Stock #:
- T360660
- VIN:
- 5TDKDRBH8TS603686
Preparing for a close up...
Photos coming soon
New arrival
2026 Toyota Highlander
Platinum AWD
New car
E Swanzey, NH
46 mi away
New car
TSRP $57,012
$53,597
- Year:
- 2026
- 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:
- Gray (Graphite)
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- 5707N
- VIN:
- 5TDKDRBH7TS597170
Preparing for a close up...
Photos coming soon
2026 Toyota Highlander
XLE AWD
New car
Torrington, CT
41 mi away
New car
TSRP $48,453
$48,453
- Year:
- 2026
- 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 Softexfab
- Transmission:
- 8-Speed Automatic
- Stock #:
- TS24A515
- VIN:
- 5TDKDRBH5TS612717
Preparing for a close up...
Photos coming soon
New arrival
2026 Toyota Highlander
XLE AWD
New car
E Swanzey, NH
46 mi away
New car
No Price Listed
- Year:
- 2026
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- TM26-890
- VIN:
- 5TDKDRBH6TS612273
Preparing for a close up...
Photos coming soon
Price drop
-$2,987
2026 Toyota Highlander
XLE AWD
New car
Home delivery from Milford, MA
Price includes $105 shipping
New car
TSRP $48,328
$48,528
$45,541
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- HEAVY METAL
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- TS596337
- VIN:
- 5TDKDRBH1TS596337
Preparing for a close up...
Photos coming soon
2026 Toyota Highlander
XLE AWD
New car
Home delivery from Milford, MA
Price includes $105 shipping
New car
TSRP $49,122
$49,322
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Pearl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- AT613130
- VIN:
- 5TDKDRBH0TS613130
Preparing for a close up...
Photos coming soon
New arrival
2026 Toyota Highlander
XLE AWD
New car
Home delivery from Gorham, NH
Price includes $158 shipping
New car
TSRP $49,612
$50,569
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Wind Chill Prl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black (Blk Lth)
- Transmission:
- 8-Speed Automatic
- Stock #:
- TS612399
- VIN:
- 5TDKDRBH6TS612399
Preparing for a close up...
Photos coming soon
New arrival
2026 Toyota Highlander
Limited AWD
New car
Home delivery from Avenel, NJ
Price includes $432 shipping
New car
TSRP $56,971
No Price Listed
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Wind Chill Prl
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black (Blk Lth)
- Transmission:
- 8-Speed Automatic
- Stock #:
- TS612494
- VIN:
- 5TDKDRBH0TS612494
Preparing for a close up...
Photos coming soon
New arrival
2026 Toyota Highlander
Platinum AWD
New car
Home delivery from Avenel, NJ
Price includes $432 shipping
New car
TSRP $58,931
No Price Listed
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Red
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 4,493
- Stock #:
- 26350531
- VIN:
- 5TDKDRBH7TS598139
2026 Toyota Highlander
XSE AWD
4,493 mi
Store transfer to Hartford, CT
Price includes $1,199 shipping
High Priced
$51,197
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 2,553
- Stock #:
- 70031543
- VIN:
- 5TDKDRBH3TS606107
2026 Toyota Highlander
XLE AWD
2,553 mi
Store transfer to Hartford, CT
Price includes $249 shipping
High Priced
$50,247
2027 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2027 Toyota Highlander prices has changed over time.
See more price trendsAVG Price
Not Available
2027 Toyota Highlander
Index Price
$29,168
0.1%
All used vehicles
2027 Toyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New Model Premium: The 2026 Highlander is priced at $51,737, reflecting a 12% increase over its MSRP, indicating strong demand for the latest model.
- Steep Depreciation for Older Models: The 2019 Highlander shows a significant drop, with an average price of $24,537, representing a -23.5% depreciation from its original MSRP.
- Best Value in Recent Models: The 2022 Highlander is priced at $33,940, which is -5.1% below its MSRP, making it a competitive option for buyers seeking value.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $46,270 | $51,737 | +11.9% |
| 2025 Toyota Highlander | $40,320 | $41,573 | +3.1% |
| 2024 Toyota Highlander | $39,270 | $39,197 | -0.2% |
| 2023 Toyota Highlander | $36,620 | $36,418 | -0.6% |
| 2022 Toyota Highlander | $35,855 | $33,940 | -5.1% |
| 2021 Toyota Highlander | $35,085 | $30,923 | -12.0% |
| 2020 Toyota Highlander | $34,600 | $28,787 | -16.8% |
| 2019 Toyota Highlander | $31,830 | $24,537 | -23.5% |
| 2018 Toyota Highlander | $31,230 | $22,596 | -27.7% |
| 2017 Toyota Highlander | $30,630 | $20,935 | -31.7% |
| 2016 Toyota Highlander | $30,490 | $18,897 | -38.1% |
| 2015 Toyota Highlander | $29,765 | $17,326 | -41.7% |
These recommendations are based on CarGurus' proprietary market data from July 2, 2026, CarGurus experts' opinions, and generative AI.
FAQs
How many 2027 Toyota Highlander vehicles in Chesterfield, MA have no reported accidents or damage?
6 out of 6 for sale near Chesterfield, MA have no reported accidents or damage.
What is the fuel economy of the 2027 Toyota Highlander?
Depending on the engine and options, the 2027 Toyota Highlander gets between 24 and 24 MPG (or EV battery range).
What fuel types are available?
Gasoline engines are available.
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