New & Used 2027 Toyota Grand Highlander for Sale nearWinchester, VA
223 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Portobello
- Transmission:
- 8-Speed Automatic
- Mileage:
- 12,365
- Stock #:
- BC0811A
- VIN:
- 5TDAAAB56TS132259
New arrival
Sponsored by Ourisman Chrysler Dodge Jeep Ram Fiat of Baltimore
2026 Toyota Grand Highlander
Platinum AWD
12,365 mi
Baltimore, MD
88 mi away
Good Deal
$56,800
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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 Leather
- Transmission:
- Automatic
- Mileage:
- 11,700
- Stock #:
- 5285890
- VIN:
- 5TDAAAB56TS129796
Price drop
-$1,295
Sponsored Listing
2026 Toyota Grand Highlander
XLE AWD
11,700 mi
Baltimore, MD
80 mi away
Great Deal
$44,294
$42,999
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 11,822
- Stock #:
- 168847
- VIN:
- 5TDAAAB53TS127472
Sponsored Listing
2026 Toyota Grand Highlander
Limited AWD
11,822 mi
Duncansville, PA
90 mi away
Good Deal
$53,468
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- KTTTS158420
- VIN:
- 5TDAAAB57TS158420
New arrival
2026 Toyota Grand Highlander
Platinum AWD
Vienna, VA
52 mi away
New car
No Price Listed
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- Portobello Leather
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 154937
- VIN:
- 5TDAAAB52TS154937
2026 Toyota Grand Highlander
Platinum AWD
Home delivery from DeRidder, LA
Price includes $1,544 shipping
New car
TSRP $58,437
$59,980
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- KTWTS157661
- VIN:
- 5TDAAAB52TS157661
2026 Toyota Grand Highlander
Platinum AWD
Westminster, MD
69 mi away
New car
TSRP $58,508
$59,308
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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)
- Transmission:
- 8-Speed Automatic
- Stock #:
- Q159581
- VIN:
- 5TDAAAB53TS159581
New arrival
2026 Toyota Grand Highlander
XLE AWD
Stafford, VA
63 mi away
New car
TSRP $49,573
$49,571
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- 3
- Stock #:
- T153429
- VIN:
- 5TDAAAB50TS153429
2026 Toyota Grand Highlander
XLE AWD
Suitland, MD
71 mi away
New car
TSRP $49,128
$49,428
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Storm Cloud
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 5
- Stock #:
- TS157220
- VIN:
- 5TDAAAB55TS157220
2026 Toyota Grand Highlander
XLE AWD
Leesburg, VA
34 mi away
New car
TSRP $48,613
$49,611
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Celestial Silver Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black SofTex® trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 155699
- VIN:
- 5TDAAAB56TS155699
2026 Toyota Grand Highlander
XLE AWD
Home delivery from DeRidder, LA
Price includes $1,544 shipping
New car
TSRP $49,372
$50,916
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Stock #:
- 62E2121
- VIN:
- 5TDAAAB59TS159035
Price drop
-$2,800
2026 Toyota Grand Highlander
Platinum AWD
Baltimore, MD
87 mi away
New car
TSRP $57,903
$57,703
$55,703
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Cloud)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Light Gray
- Transmission:
- 8-Speed Automatic
- Stock #:
- TS149709
- VIN:
- 5TDAAAB58TS149709
2026 Toyota Grand Highlander
Platinum AWD
Woodbridge, VA
61 mi away
New car
TSRP $57,533
$58,532
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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
- Stock #:
- T149827
- VIN:
- 5TDAAAB53TS149827
Price drop
-$1,490
2026 Toyota Grand Highlander
XLE AWD
Chambersburg, PA
60 mi away
New car
TSRP $50,438
$49,428
$48,428
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- Black leather trim
- Transmission:
- 8-Speed Dual Clutch
- Mileage:
- 0
- Stock #:
- 44F994
- VIN:
- 5TDAAAB56TS44F994
2026 Toyota Grand Highlander
Limited AWD
Winchester, VA
1 mi away
New car
TSRP $56,093
$58,083
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Celestial Silve
- Combined gas mileage:
- 24 MPG
- Fuel type:
- Gasoline
- Interior color:
- Light Gray
- Transmission:
- 8-Speed Automatic
- Stock #:
- 62F2196
- VIN:
- 5TDAAAB58TS158796
New arrival
2026 Toyota Grand Highlander
XLE AWD
Frederick, MD
43 mi away
New car
TSRP $48,893
$49,693
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Portobello
- Transmission:
- 8-Speed Automatic
- Stock #:
- 62A2486
- VIN:
- 5TDAAAB51TS158218
New arrival
2026 Toyota Grand Highlander
Platinum AWD
Silver Spring, MD
65 mi away
New car
TSRP $58,008
No Price Listed
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- Automatic
- Mileage:
- 10
- Stock #:
- TS43F403
- VIN:
- 5TDAAAB56TS43F403
2026 Toyota Grand Highlander
XLE AWD
Nottingham, MD
90 mi away
New car
TSRP $48,718
$49,517
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- KTTTS157681
- VIN:
- 5TDAAAB58TS157681
2026 Toyota Grand Highlander
Limited AWD
Vienna, VA
52 mi away
New car
No Price Listed
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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 #:
- 62E2110
- VIN:
- 5TDAAAB54TS156303
2026 Toyota Grand Highlander
XLE AWD
Baltimore, MD
87 mi away
New car
TSRP $49,088
$49,888
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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 #:
- 62E2118
- VIN:
- 5TDAAAB51TS158199
Price drop
-$1,800
2026 Toyota Grand Highlander
XLE AWD
Baltimore, MD
87 mi away
New car
TSRP $49,088
$49,888
$48,888
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- Blueprint
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Light Gray Leather
- Mileage:
- 1
- Stock #:
- 159505
- VIN:
- 5TDAAAB59TS159505
New arrival
2026 Toyota Grand Highlander
Limited AWD
Johnstown, PA
87 mi away
New car
TSRP $55,618
$56,108
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Exterior color:
- White (Cloud)
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Lt Gry Lth
- Transmission:
- 8-Speed Automatic
- Stock #:
- Q157731
- VIN:
- 5TDAAAB58TS157731
2026 Toyota Grand Highlander
Limited AWD
Stafford, VA
63 mi away
New car
TSRP $56,383
$56,381
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand Highlander
- Body type:
- SUV / Crossover
- Doors:
- 4 doors
- Drivetrain:
- All-Wheel Drive
- Engine:
- 265 hp 2.4L I4
- Combined gas mileage:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 1
- Stock #:
- KATTS159002
- VIN:
- 5TDAAAB55TS159002
New arrival
2026 Toyota Grand Highlander
Limited AWD
Annapolis, MD
90 mi away
New car
No Price Listed
- Year:
- 2026
- Make:
- Toyota
- Model:
- Grand 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:
- 23 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 8,936
- Stock #:
- PB14402
- VIN:
- 5TDAAAB56TS113453
Sponsored Listing
2026 Toyota Grand Highlander
Limited AWD
8,936 mi
Bethesda, MD
56 mi away
Good Deal
$53,800
2027 Toyota Grand Highlander Trims
| Trim type | MSRP |
|---|---|
| XLE FWD | $45,430 |
| Platinum AWD | $55,745 |
| Limited AWD | $51,660 |
| Limited FWD | $50,060 |
| LE AWD | $44,160 |
| LE FWD | $42,560 |
| XLE AWD | $47,030 |
*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.
2027 Toyota Grand Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2027 Toyota Grand Highlander prices has changed over time.
See more price trendsAVG Price
Not Available
2027 Toyota Grand Highlander
Index Price
$28,617
1.1%
All used vehicles
2027 Toyota Grand Highlander Pricing Analysis
Pricing by Trim Packages
Key Insights
- Volume Leader: The XLE AWD trim leads with 925 listings, indicating strong demand for this configuration.
- Premium Spread: The Platinum AWD trim has the highest MSRP at $55,745, reflecting a $8,715 premium over the XLE AWD.
- Drivetrain Effect: AWD trims dominate inventory with 1,697 total listings compared to 562 for FWD trims, suggesting a preference for all-wheel drive in this segment.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 925 | $47,030 | AWD | 2.4L 265 hp I4 |
| Platinum AWD | 421 | $55,745 | AWD | 2.4L 265 hp I4 |
| XLE FWD | 362 | $45,430 | FWD | 2.4L 265 hp I4 |
| Limited AWD | 323 | $51,660 | AWD | 2.4L 265 hp I4 |
| Limited FWD | 180 | $50,060 | FWD | 2.4L 265 hp I4 |
| LE FWD | 42 | $42,560 | FWD | 2.4L 265 hp I4 |
| LE AWD | 28 | $44,160 | AWD | 2.4L 265 hp I4 |
Pricing Analysis by Model Year
Key Insights
- New-Car Premium: The 2026 model shows a significant average price of $51,760, which is 22.5% above its starting MSRP of $42,260.
- Depreciation Curve: The 2024 model has the smallest average price increase over MSRP at 0.1%, indicating minimal depreciation.
- Best Value Sweet Spot: The 2025 model offers a balanced average price of $45,056, which is 10.3% above its starting MSRP, making it a potential sweet spot for buyers.
Model Year Pricing
| Model Year | Starting MSRP | Avg Price | Avg Price vs Starting MSRP |
|---|---|---|---|
| 2026 | $42,260 | $51,760 | +22.5% |
| 2025 | $40,860 | $45,056 | +10.3% |
| 2024 | $43,320 | $43,376 | +0.1% |
These recommendations are based on CarGurus' proprietary market data from October 21, 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 Grand Highlander vehicles in Winchester, VA have no reported accidents or damage?
13 out of 15 for sale near Winchester, VA have no reported accidents or damage.
What is the fuel economy of the 2027 Toyota Grand Highlander?
Depending on the engine and options, the 2027 Toyota Grand Highlander gets between 22 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.
Relevant articles
The CarGurus Editorial Team
The Most Spacious SUVs in 2026
Which SUV has the most interior space? Our guide has the lowdown, with fdetails of the most spacious SUVs in each category.
The CarGurus Editorial Team
The Best Family Vehicles Under $35,000 in 2026
You can still get a great family car for under $35k, and you don't have to compromise on meeting your family's needs. Here, CarGurus editors pick 10 new and used vehicles that fit that budget, taking safety, practicality, and comfort into consideration.
CarGurus Editorial Team
The Best 3-Row SUVs with Great Gas Mileage in 2026
There are lots of 3-row SUVs that give you great gas mileage. Here we've listed our top choices, each of which gives you excellent mpg and seven-seat practicality.
2027 Toyota Grand Highlander in Hagerstown MD2027 Toyota Grand Highlander in Cumberland MD2027 Toyota Grand Highlander in Manassas VA2027 Toyota Grand Highlander in Harrisonburg VA2027 Toyota Grand Highlander in Washington DC2027 Toyota Grand Highlander in Fredericksburg VA2027 Toyota Grand Highlander in Hanover PA2027 Toyota Grand Highlander in Charlottesville VA2027 Toyota Grand Highlander in Baltimore MD
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in WinchesterUsed SUVs / Crossovers for Sale with Low Mileage in WinchesterUsed Hatchbacks for Sale with Low Mileage in WinchesterUsed Convertibles for Sale with Low Mileage in WinchesterUsed Vans for Sale with Low Mileage in WinchesterUsed Minivans for Sale with Low Mileage in WinchesterUsed Pickup Trucks for Sale with Low Mileage in WinchesterUsed Coupes for Sale with Low Mileage in WinchesterUsed Wagons for Sale with Low Mileage in Winchester
