Used 2019 Toyota Highlander for Sale near Winchester, VA

277 results

Winchester, VA

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2018 Toyota Highlander

XLE

167,253 miles

$17,231

Fair Deal

Charlottesville, VA

80 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Predawn Gray Mica
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 167,253
Stock number:: KR290141A
VIN:: 5TDKZRFH2JS545857

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2018 Toyota Highlander

Limited

92,854 miles

$23,244

Fair Deal

Baltimore, MD

76 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: White (Blizzard Pearl)
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Ash
Transmission:: 8-Speed Automatic
Mileage:: 92,854
Stock number:: H60031A
VIN:: 5TDYZRFHXJS259751

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2018 Toyota Highlander

Limited Platinum AWD

72,079 miles

$28,287

Fair Deal

Chambersburg, PA

59 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Black
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 72,079
Stock number:: 871627AP
VIN:: 5TDDZRFH3JS871627

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2019 Toyota Highlander

Limited AWD

69,461 miles

$27,783

Great Deal

Harrisonburg, VA

63 mi away

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Celestial Silver Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 69,461
Stock number:: 28593
VIN:: 5TDDZRFH2KS981134

2020 Toyota Highlander

XLE AWD

140,756 miles

$19,900

Great Deal

Elkins, WV

93 mi away

Year:: 2020
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 140,756
Stock number:: F25196B
VIN:: 5TDGZRBH5LS027370

2018 Toyota Highlander

Limited AWD

92,398 miles

$23,000

Great Deal

Certified Pre-Owned

Warrenton, VA

37 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Midnight Black Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 92,398
Stock number:: W250528A
VIN:: 5TDDZRFH0JS853747

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2018 Toyota Highlander

LE AWD

94,540 miles

$18,500

Great Deal

Ebensburg, PA

95 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Gold
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Almond
Transmission:: 8-Speed Automatic
Mileage:: 94,540
Stock number:: C2519A
VIN:: 5TDBZRFH9JS911653

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2019 Toyota Highlander

Limited AWD

78,835 miles

$26,449

Good Deal

Westminster, MD

70 mi away

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Midnight Black Metallic
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: Automatic
Mileage:: 78,835
Stock number:: BV1664
VIN:: 5TDDZRFH8KS942516

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2019 Toyota Highlander

LE Plus FWD

41,135 miles

$24,938

Fair Deal

Clarksville, MD

66 mi away

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Midnight Black Metallic
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Ash
Transmission:: Automatic
Mileage:: 41,135
Stock number:: 261000B
VIN:: 5TDZZRFH1KS356908

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2020 Toyota Highlander

XLE AWD

81,564 miles

$26,531

Good Deal

Suitland, MD

71 mi away

Year:: 2020
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Silver
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 81,564
Stock number:: 6793A
VIN:: 5TDHZRBH6LS506174

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2019 Toyota Highlander

Limited AWD

88,823 miles

$26,747

Good Deal

Store transfer to Winchester, VA

634 mi away Price includes $749 shipping Price includes $749 shipping

Year:: 2019
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Red (Burgundy)
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: CREAM
Transmission:: Automatic
Mileage:: 88,823
Stock number:: 27645103
VIN:: 5TDDZRFH8KS992560

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2018 Toyota Highlander

Limited Platinum AWD

96,137 miles

$24,412

Good Deal

Annapolis, MD

88 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Predawn Gray Mica
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 96,137
Stock number:: R8481P
VIN:: 5TDDZRFH5JS892320

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2018 Toyota Highlander

Limited AWD

100,036 miles

$19,999

Great Deal

Waldorf, MD

78 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Gray
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Silver
Transmission:: 8-Speed Automatic
Mileage:: 100,036
Stock number:: 11058
VIN:: 5TDDZRFH4JS864850

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2018 Toyota Highlander

LE AWD

90,058 miles

$20,399

Fair Deal

Charlottesville, VA

77 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: White
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Transmission:: Automatic
Mileage:: 90,058
Stock number:: 39SD2524A
VIN:: 5TDBZRFH3JS811564

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2020 Toyota Highlander

XLE AWD

46,045 miles

$29,988

Good Deal

Rockville, MD

57 mi away

Year:: 2020
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Moon Dust
Combined gas mileage:: 23 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 46,045
Stock number:: G303290B
VIN:: 5TDGZRBH8LS008134

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2020 Toyota Highlander

Platinum FWD

107,172 miles

$28,997

Fair Deal

Store transfer to Winchester, VA

2,375 mi away Price includes $1,999 shipping Price includes $1,999 shipping

Year:: 2020
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: Front-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: White
Combined gas mileage:: 24 MPG
Fuel type:: Gasoline
Interior color:: Gray
Transmission:: Automatic
Mileage:: 107,172
Stock number:: 27562998
VIN:: 5TDFZRAH9LS017373

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2018 Toyota Highlander

XLE AWD

96,725 miles

$21,599

Fair Deal

Silver Spring, MD

65 mi away

Year:: 2018
Make:: Toyota
Model:: Highlander
Body type:: SUV / Crossover
Doors:: 4 doors
Drivetrain:: All-Wheel Drive
Engine:: 295 hp 3.5L V6
Exterior color:: Ooh La La Rouge Mica
Combined gas mileage:: 22 MPG
Fuel type:: Gasoline
Interior color:: Black
Transmission:: 8-Speed Automatic
Mileage:: 96,725
Stock number:: 52F4031A
VIN:: 5TDJZRFH6JS494536

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Overview

Reviews

FAQs

CarGurus Analysis: 2019 Toyota Highlander

Summary

With 3,121 currently listed for sale on CarGurus and an average price of $24,070.10, 35.2% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.6 / 5 stars.
65.8% of 2019 Highlander models on CarGurus are accident free.
The 2019 Toyota Highlander combined stylish design with a spacious interior, offering up to eight-passenger seating and advanced safety features, earning high reliability ratings and excellent resale value.

Why it stands out

The 2019 Toyota Highlander excelled as a family-friendly SUV with its stylish design and spacious interior, accommodating up to eight passengers with ease. It stood out for its comprehensive suite of active safety features, which were often rare in competitors at the time, earning it top safety ratings year after year. Additionally, the available V6 engine provided a strong balance of power and efficiency, making it a practical choice for buyers seeking reliability and value in their vehicle.

Other model years to consider

2022 Toyota Highlander: This year offers $33,778.03 average price, 36% good/great deals, 4.6/5 user rating, 8.2/10 expert rating, 6,393 listings.
2021 Toyota Highlander: This year offers $30,393.06 average price, 36% good/great deals, 4.8/5 user rating, 7.5/10 expert rating, 4,492 listings.
2016 Toyota Highlander: This year offers $18,379.95 average price, 38% good/great deals, 4.6/5 user rating, 1,968 listings.

This analysis is based on CarGurus' proprietary market data from December 9, 2025, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(83 reviews)

Anonymous

5.0

Reviewed a 2019 Toyota Highlander on Sep 03, 2024

great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort

Jordan A

5.0

Reviewed a 2019 Toyota Highlander on Feb 07, 2024

Great value! I absolutely love the heated seats and back up camera.

Suzanne M

5.0

Reviewed a 2019 Toyota Highlander on Oct 11, 2024

It’s roomy, has all the bells and whistles. Nice smooth ride. Takes a little time to manipulate all the “bells and whistles”. Also aesthetically good .

Candice O

4.0

Reviewed a 2019 Toyota Highlander on Jul 22, 2024

Drives very nicely, compared to new ford explorer which drove terrible and had constant bells. Front seats are terrible compared to 2004 Highlander. Headrests are so forward I had to be unsafe and turn them around so I did not constantly have a headache while driving. Will have to buy cushions to correct this. No knee room in passenger seat as dash board very low. Has decent size cup holders in front compared to small ones in new Highlander. Back seat is larger and more comfortable for kids than old Highlander, stealing from the 3rd row. Storage is about the same.

Anonymous

5.0

Reviewed a 2019 Toyota Highlander on Jan 16, 2022

Our family absolutely LOVES this vehicle. Glad that we bought it. No regrets.

2019 Toyota Highlander FAQs

How much does the 2019 Toyota Highlander cost in Winchester, VA?

The average 2019 Toyota Highlander costs about $24,070.09. The average price has decreased by -7.4% since last year. The 187 for sale near Winchester, VA on CarGurus, range from $12,999 to $36,998 in price.

How many 2019 Toyota Highlander vehicles in Winchester, VA have no reported accidents or damage?

187 out of 187 for sale near Winchester, VA have no reported accidents or damage.

What is the fuel economy of the 2019 Toyota Highlander?

Depending on the engine and options, the 2019 Toyota Highlander gets between 22 and 23 MPG (or MPGe).

What fuel types are available?

Gasoline engines are available.

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