Used Toyota Highlander for Sale nearWinsted, CT
46 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- 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:
- 11,302
- Stock #:
- LT9474
- VIN:
- 5TDKDRBH8TS607382
Sponsored by Lynch Toyota
2026 Toyota Highlander
XLE AWD
11,302 mi
Manchester, CT
32 mi away
Fair Deal
$48,694
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 13,828
- Stock #:
- WTP9502
- VIN:
- 5TDKDRBH1TS603934
Price drop
-$1,374
2026 Toyota Highlander
XLE AWD
13,828 mi
Wappingers Falls, NY
49 mi away
Great Deal
$44,795
$43,596
- 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:
- 11,302
- Stock #:
- LT9474
- VIN:
- 5TDKDRBH8TS607382
2026 Toyota Highlander
XLE AWD
11,302 mi
Manchester, CT
32 mi away
Fair Deal
$48,694
- 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:
- 12,417
- Stock #:
- 28871221
- VIN:
- 5TDKDRBHXTS597518
New arrival
2026 Toyota Highlander
XSE AWD
12,417 mi
Store transfer to Hartford, CT
Price includes $1,499 shipping
Fair Deal
$50,497
- 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:
- 9,652
- Stock #:
- T599934R
- VIN:
- 5TDKDRBH1TS599934
Price drop
-$2,280
2026 Toyota Highlander
XLE AWD
9,652 mi
Home delivery from Avenel, NJ
Price includes $339 shipping
Great Deal
$48,997
$46,717
- 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:
- Gray
- Transmission:
- Automatic
- Mileage:
- 9,003
- Stock #:
- 28676351
- VIN:
- 5TDKDRBH3TS601084
New arrival
2026 Toyota Highlander
XLE AWD
9,003 mi
Store transfer to Hartford, CT
Price includes $149 shipping
Fair Deal
$48,147
- 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:
- Black Softexfab
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- 614826
- VIN:
- 5TDKDRBH9TS614826
2026 Toyota Highlander
XLE AWD
Home delivery from Marina Del Rey, CA
Price includes $4,378 shipping
New car
TSRP $48,778
$52,278
- 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 #:
- TT261789
- VIN:
- 5TDKDRBH0TS35A304
2026 Toyota Highlander
XSE AWD
Manchester, CT
32 mi away
New car
TSRP $52,338
$53,037
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 1
- Stock #:
- 617819
- VIN:
- 5TDKDRBH5TS617819
2026 Toyota Highlander
XSE AWD
Home delivery from Marina Del Rey, CA
Price includes $4,378 shipping
New car
TSRP $52,043
$56,544
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- TS619586
- VIN:
- 5TDKDRBH7TS619586
New arrival
2026 Toyota Highlander
Platinum AWD
Kingston, NY
46 mi away
New car
TSRP $56,073
$55,248
- 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:
- 0
- Stock #:
- TT261904
- VIN:
- 5TDKDRBH0TS39A785
2026 Toyota Highlander
XLE AWD
Manchester, CT
32 mi away
New car
TSRP $49,978
$50,677
- 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
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite Leather Trim)
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 2
- Stock #:
- 7426
- VIN:
- 5TDKDRBH7TS620351
2026 Toyota Highlander
Platinum AWD
Hudson, NY
41 mi away
New car
TSRP $57,142
$57,317
- 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
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite Leather Trim)
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 7333
- VIN:
- 5TDKDRBH9TS615152
2026 Toyota Highlander
Platinum AWD
Hudson, NY
41 mi away
New car
TSRP $57,272
$57,447
- 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:
- Black
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- TS616104
- VIN:
- 5TDKDRBH3TS616104
2026 Toyota Highlander
XLE AWD
Kingston, NY
46 mi away
New car
TSRP $42,212
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:
- Blue
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 2
- Stock #:
- TS615849
- VIN:
- 5TDKDRBH4TS615849
2026 Toyota Highlander
XLE AWD
Kingston, NY
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:
- Heavy Metal
- Fuel type:
- Gasoline
- Interior color:
- Black leather trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 621094
- VIN:
- 5TDKDRBH7TS621094
New arrival
2026 Toyota Highlander
Limited AWD
West Simsbury, CT
15 mi away
New car
TSRP $54,258
$54,258
- 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 #:
- TJT1066
- VIN:
- 5TDKDRBH4TS621389
New arrival
2026 Toyota Highlander
XSE AWD
Home delivery from Laconia, NH
Price includes $276 shipping
New car
TSRP $52,683
$52,258
- 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:
- Black
- Transmission:
- 8-Speed Automatic
- Stock #:
- TS615795
- VIN:
- 5TDKDRBH7TS615795
2026 Toyota Highlander
Limited AWD
Home delivery from Avenel, NJ
Price includes $339 shipping
New car
TSRP $56,781
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:
- 7
- Stock #:
- CT8895
- VIN:
- 5TDKDRBH9TS619296
Photos coming soon
2026 Toyota Highlander
XLE AWD
Home delivery from Salem, NH
Price includes $139 shipping
New car
TSRP $49,168
$46,421
- 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
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5
- Stock #:
- TCT8622
- VIN:
- 5TDKDRBH2TS30J505
Photos coming soon
2026 Toyota Highlander
Platinum AWD
Home delivery from Salem, NH
Price includes $139 shipping
New car
TSRP $56,872
$53,544
- Year:
- 2026
- Make:
- Toyota
- Model:
- Highlander
- Body type:
- SUV / Crossover
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Wind Chill Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 5
- Stock #:
- TCT9177
- VIN:
- 5TDKDRBH7TS39A380
Photos coming soon
2026 Toyota Highlander
Home delivery from Salem, NH
Price includes $139 shipping
New car
TSRP $50,233
$47,363
- 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:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2,068
- Stock #:
- 57829
- VIN:
- 5TDKDRBH2TS610651
Photos coming soon
2026 Toyota Highlander
Limited AWD
2,068 mi
Home delivery from Commack, NY
Price includes $117 shipping
No Rating
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:
- Heavy Metal
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 3
- Stock #:
- 267322
- VIN:
- 5TDKDRBH0TS619333
Photos coming soon
New arrival
2026 Toyota Highlander
XLE AWD
Hartford, CT
25 mi away
New car
TSRP $48,728
$49,027
- 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 LEATHER TRIM)
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- 48845
- VIN:
- 5TDKDRBH5TS620350
2026 Toyota Highlander
Home delivery from St Albans, VT
Price includes $197 shipping
New car
TSRP $54,792
$55,488
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
$28,747
1.1%
All used vehicles
2027 Toyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New-Car Premium: The 2026 model year has an average price of $50,505, reflecting a 9.2% premium over its starting MSRP of $46,270.
- Steepest Depreciation: The 2016 model year exhibits the steepest depreciation at -40.0%, indicating significant value loss over time.
- Best Value Sweet Spot: The 2024 model year is priced at an average of $39,224, which is only -0.1% below its starting MSRP, suggesting it may offer the best value for budget-conscious shoppers.
Model Year Pricing
| Model Year | Starting MSRP | Avg Price | Avg Price vs Starting MSRP |
|---|---|---|---|
| 2026 | $46,270 | $50,505 | +9.2% |
| 2025 | $40,320 | $42,255 | +4.8% |
| 2024 | $39,270 | $39,224 | -0.1% |
| 2023 | $36,620 | $35,133 | -4.1% |
| 2022 | $35,855 | $32,474 | -9.4% |
| 2021 | $35,085 | $30,151 | -14.1% |
| 2020 | $34,600 | $28,111 | -18.8% |
| 2019 | $31,830 | $23,922 | -24.8% |
| 2018 | $31,230 | $21,837 | -30.1% |
| 2017 | $30,630 | $20,563 | -32.9% |
| 2016 | $30,490 | $18,303 | -40.0% |
These recommendations are based on CarGurus' proprietary market data from September 30, 2026, CarGurus experts' opinions, and generative AI.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
FAQs
How many 2027 Toyota Highlander vehicles in Winsted, CT have no reported accidents or damage?
8 out of 8 for sale near Winsted, CT 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/MPGe.
What fuel types are available?
Gasoline engines are available.
*CarGurus meticulously monitors the prices of millions of pre-owned vehicle listings, offering users precise and up-to-date market insights. Historical pricing data excludes any additional dealer fees as of May 3, 2026.
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