Used Toyota Highlander for Sale nearChestertown, MD
44 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:
- 13,872
- Stock #:
- P1B0794
- VIN:
- 5TDKDRBH9TS607049
Sponsored Listing
2026 Toyota Highlander
XLE AWD
13,872 mi
Silver Spring, MD
48 mi away
Fair Deal
$48,058
- 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:
- 14,027
- Stock #:
- P129193
- VIN:
- 5TDKDRBH6TS605727
Sponsored Listing
2026 Toyota Highlander
XLE AWD
14,027 mi
Milford, DE
38 mi away
Fair Deal
$47,794
- 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:
- 14,027
- Stock #:
- P129193
- VIN:
- 5TDKDRBH6TS605727
2026 Toyota Highlander
XLE AWD
14,027 mi
Milford, DE
38 mi away
Fair Deal
$47,794
- 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:
- 13,872
- Stock #:
- P1B0794
- VIN:
- 5TDKDRBH9TS607049
2026 Toyota Highlander
XLE AWD
13,872 mi
Silver Spring, MD
48 mi away
Fair Deal
$48,058
- 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
Price drop
-$1,900
2026 Toyota Highlander
Limited AWD
2,068 mi
Home delivery from Commack, NY
Price includes $279 shipping
Great Deal
$50,349
$48,449
- 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
2026 Toyota Highlander
XSE AWD
12,417 mi
Store transfer to White Marsh, MD
Price includes $1,599 shipping
Fair Deal
$49,597
- 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:
- Heavy Metal
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 9,652
- Stock #:
- T599934R
- VIN:
- 5TDKDRBH1TS599934
2026 Toyota Highlander
XLE AWD
9,652 mi
Home delivery from Avenel, NJ
Price includes $402 shipping
Fair Deal
$48,060
- 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:
- 13,835
- Stock #:
- 70230125
- VIN:
- 5TDKDRBH5TS596969
New arrival
2026 Toyota Highlander
Limited AWD
13,835 mi
Store transfer to White Marsh, MD
Price includes $1,999 shipping
Fair Deal
$51,997
- 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:
- Midnight Black Metallic
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite)
- Transmission:
- 8-Speed Automatic
- Mileage:
- 2,760
- Stock #:
- K260812228T1
- VIN:
- 5TDKDRBH5TS609803
2026 Toyota Highlander
XLE AWD
2,760 mi
Home delivery from Miami Lakes, FL
Price includes $2,856 shipping
Fair Deal
$50,302
- 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 $4,125 shipping
New car
TSRP $48,778
$52,025
- 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:
- 10
- Stock #:
- 0601
- VIN:
- 5TDKDRBH3TS618726
Price drop
-$1,300
2026 Toyota Highlander
Platinum AWD
Edgewood, MD
21 mi away
New car
TSRP $56,383
$56,300
$55,000
- 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 (Ruby Flare Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Black Softex®/Fabric Mixed Media Trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 5,081
- Stock #:
- T260948
- VIN:
- 5TDKDRBH1TS613489
Price drop
-$1,500
2026 Toyota Highlander
XSE AWD
Easton, MD
33 mi away
New car
TSRP $52,932
$53,032
$51,532
- 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:
- Automatic
- Mileage:
- 0
- Stock #:
- 260540
- VIN:
- 5TDKDRBH2TS622749
New arrival
2026 Toyota Highlander
XLE AWD
Clarksville, MD
47 mi away
New car
TSRP $48,988
$50,586
- 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:
- 0
- Stock #:
- T260827
- VIN:
- 5TDKDRBH0TS622197
New arrival
2026 Toyota Highlander
Limited AWD
Easton, MD
33 mi away
New car
TSRP $55,391
$55,491
- 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)
- Fuel type:
- Gasoline
- Interior color:
- Glazed Caramel Leather Trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 4
- Stock #:
- T260819
- VIN:
- 5TDKDRBH1TS621527
2026 Toyota Highlander
Platinum AWD
Easton, MD
33 mi away
New car
TSRP $57,263
$57,363
- 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:
- Heavy Metal
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black (Blk)
- Transmission:
- 8-Speed Automatic
- Stock #:
- R620898
- VIN:
- 5TDKDRBH9TS620898
2026 Toyota Highlander
XLE AWD
Home delivery from Woodbridge, VA
Price includes $380 shipping
New car
TSRP $49,257
$50,636
- 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
- Stock #:
- I32856
- VIN:
- 5TDKDRBH4TS620436
2026 Toyota Highlander
Platinum AWD
Cockeysville, MD
36 mi away
New car
TSRP $56,383
$56,181
- 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 $4,125 shipping
New car
TSRP $52,043
$56,290
- 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 (Ruby Flare Pearl)
- Fuel type:
- Gasoline
- Interior color:
- Gray (Graphite leather trim)
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 621304
- VIN:
- 5TDKDRBH3TS621304
New arrival
2026 Toyota Highlander
Platinum AWD
Home delivery from DeRidder, LA
Price includes $1,695 shipping
New car
TSRP $56,782
$58,716
- 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 Pear
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Stock #:
- 62E2117
- VIN:
- 5TDKDRBH9TS621713
New arrival
2026 Toyota Highlander
XLE AWD
Baltimore, MD
26 mi away
New car
TSRP $49,463
$49,263
- 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
- Stock #:
- TS619660
- VIN:
- 5TDKDRBH4TS619660
2026 Toyota Highlander
Limited AWD
Home delivery from Avenel, NJ
Price includes $402 shipping
New car
TSRP $57,631
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:
- Blueprint
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 10
- Stock #:
- TS621021
- VIN:
- 5TDKDRBH2TS621021
2026 Toyota Highlander
Platinum AWD
Nottingham, MD
26 mi away
New car
TSRP $57,107
$57,906
- 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
- Transmission:
- 8-Speed Automatic
- Stock #:
- 62A2474
- VIN:
- 5TDKDRBH8TS621525
2026 Toyota Highlander
XLE AWD
Silver Spring, MD
49 mi away
New car
TSRP $48,783
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
- Stock #:
- 62A2463
- VIN:
- 5TDKDRBH6TS620700
2026 Toyota Highlander
Platinum AWD
Silver Spring, MD
49 mi away
New car
TSRP $56,383
No Price Listed
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
$28,728
0.9%
All used vehicles
2027 Toyota Highlander Pricing Analysis
Pricing Analysis by Model Year
Key Insights
- New-Car Premium: The 2026 model year leads with an average price of $50,268, indicating a 8.6% premium over its starting MSRP.
- Steepest Depreciation: The 2016 model year exhibits the steepest depreciation at -40.5%, highlighting significant value loss over time.
- Best Value Sweet Spot: The 2023 model year is priced at an average of $34,978, which is -4.5% below its starting MSRP, suggesting it may offer better value for budget-conscious shoppers.
Model Year Pricing
| Model Year | Starting MSRP | Avg Price | Avg Price vs Starting MSRP |
|---|---|---|---|
| 2026 | $46,270 | $50,268 | +8.6% |
| 2025 | $40,320 | $42,541 | +5.5% |
| 2024 | $39,270 | $39,070 | -0.5% |
| 2023 | $36,620 | $34,978 | -4.5% |
| 2022 | $35,855 | $32,320 | -9.9% |
| 2021 | $35,085 | $29,954 | -14.6% |
| 2020 | $34,600 | $28,122 | -18.7% |
| 2019 | $31,830 | $23,801 | -25.2% |
| 2018 | $31,230 | $21,591 | -30.9% |
| 2017 | $30,630 | $20,208 | -34.0% |
| 2016 | $30,490 | $18,149 | -40.5% |
These recommendations are based on CarGurus' proprietary market data from October 14, 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 Chestertown, MD have no reported accidents or damage?
7 out of 7 for sale near Chestertown, MD 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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