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Used Toyota Highlander for Sale near Windsor, CT

588 results
Windsor, CT
2017 Toyota Highlander Limited A Better Way Wholesale

2017 Toyota Highlander

Limited

68,562 miles

$21,495

Great Deal
Naugatuck, CT
30 mi away
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Red
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
68,562
Stock number:
200468N
VIN:
5TDYZRFH3HS200468

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2018 Toyota Highlander XLE AWD

2018 Toyota Highlander

XLE AWD

80,931 miles

$23,995

Fair Deal
Springfield, MA
20 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:
Brown
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Beige)
Transmission:
8-Speed Automatic
Mileage:
80,931
Stock number:
887453
VIN:
5TDJZRFH6JS887453

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2023 Toyota Highlander XSE AWD

2023 Toyota Highlander

XSE AWD

24,423 miles

$40,599

Fair Deal
Wilbraham, MA
23 mi away
Year:
2023
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:
24,423
Stock number:
PS519118T
VIN:
5TDKDRBH3PS519118

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2019 Toyota Highlander Limited AWD

2019 Toyota Highlander

Limited AWD

105,000 miles

$22,995

Good Deal
Vernon, CT
10 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:
105,000
Stock number:
20730R-01
VIN:
5TDDZRFH3KS924876

2021 Toyota Highlander XSE AWD

2021 Toyota Highlander

XSE AWD

83,815 miles

$29,299

Fair Deal
Bristol, CT
16 mi away
Year:
2021
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:
23 MPG
Fuel type:
Gasoline
Interior color:
Cockpit Red
Transmission:
8-Speed Automatic
Mileage:
83,815
Stock number:
UA38102A
VIN:
5TDLZRBH8MS082086

Preparing for a close up...

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2022 Toyota Highlander

XLE AWD

62,917 miles

$29,991

Great Deal
Old Saybrook, CT
41 mi away
Year:
2022
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Brown
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Transmission:
8-Speed Automatic
Mileage:
62,917
Stock number:
5135
VIN:
5TDHZRBH7NS166116

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2022 Toyota Highlander

Limited AWD

62,706 miles

$31,700

Great Deal
Westbrook, CT
41 mi away
Year:
2022
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:
23 MPG
Fuel type:
Gasoline
Interior color:
Brown (Tan)
Transmission:
Automatic
Mileage:
62,706
Stock number:
26261A
VIN:
5TDDZRBH5NS216171

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2008 Toyota Highlander

Sport

166,071 miles

$7,995

Fair Deal
Manchester, CT
9 mi away
Year:
2008
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
Front-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Magnetic Gray Metallic
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Transmission:
Automatic
Mileage:
166,071
Stock number:
032819
VIN:
JTEDS43A982032819

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2019 Toyota Highlander

Limited Platinum AWD

47,869 miles

$31,985

Fair Deal
Willimantic, CT
26 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:
47,869
Stock number:
8568
VIN:
5TDDZRFH0KS987322

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2021 Toyota Highlander

Limited AWD

117,410 miles

$24,999

Good Deal
Bristol, CT
16 mi away
Year:
2021
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Blueprint
Combined gas mileage:
23 MPG
Fuel type:
Gasoline
Interior color:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
117,410
Stock number:
UA38375A
VIN:
5TDDZRBH3MS554750

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2017 Toyota Highlander

Limited AWD

78,713 miles

$22,791

Good Deal
Watertown, CT
30 mi away
Year:
2017
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
295 hp 3.5L V6
Exterior color:
Shoreline Blue Pearl
Combined gas mileage:
22 MPG
Fuel type:
Gasoline
Interior color:
Brown (Saddle Tan)
Mileage:
78,713
Stock number:
W2041
VIN:
5TDDZRFH2HS460195

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2016 Toyota Highlander

LE AWD

90,217 miles

$17,990

Good Deal
Middletown, CT
19 mi away
Year:
2016
Make:
Toyota
Model:
Highlander
Body type:
SUV / Crossover
Doors:
4 doors
Drivetrain:
All-Wheel Drive
Engine:
270 hp 3.5L V6
Exterior color:
Shoreline Blue Pearl
Combined gas mileage:
21 MPG
Fuel type:
Gasoline
Interior color:
Black
Transmission:
Automatic
Mileage:
90,217
Stock number:
272286
VIN:
5TDBKRFH4GS272286

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2023 Toyota Highlander

XLE AWD

49,905 miles

$32,444

Great Deal
Waterbury, CT
28 mi away
Year:
2023
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:
49,905
Stock number:
U10036
VIN:
5TDKDRBH1PS039112

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2021 Toyota Highlander

Platinum AWD

96,432 miles

$31,995

Fair Deal
Naugatuck, CT
33 mi away
Year:
2021
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:
Gray (Graphite)
Transmission:
8-Speed Automatic
Mileage:
96,432
Stock number:
2110692
VIN:
5TDFZRBH8MS110692

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  1. Home
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  3. / Toyota Highlander
  4. / Connecticut
  5. / Windsor
Overview
Reviews
FAQs

CarGurus recommends the 2022 Toyota Highlander

Picture of Toyota Highlander ## Summary - With 3,958 currently listed for sale on CarGurus and an **average price of $32,739.00**, 31.5% of 2022 Toyota Highlanders for sale on CarGurus are rated as good or great deals. - **Favorably reviewed:** Owners rated the 2022 Toyota Highlander 4.58 / 5 stars. - **82.2% of 2022 Highlander models on CarGurus are accident free**. - The 2022 Toyota Highlander is commended for its safety, comfort, and the ability to deliver a smooth ride, along with a range of trims and features that cater to various family needs. ## Why it stands out The 2022 Toyota Highlander excels as a family-friendly SUV, combining essential capabilities with a touch of style. It offers a spacious three-row seating configuration, robust V6 performance, and a suite of advanced safety features, all designed to meet the demands of family life. With options for all-wheel drive and impressive towing capacity, it stands ready for both daily commutes and weekend adventures. Additionally, the Highlander's modern interior, equipped with user-friendly technology, provides convenience for busy families. Its reputation for reliability and comfort further solidifies its appeal to buyers looking for a dependable vehicle to carry their loved ones. ## Other model years to consider - **[2015 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2015-Toyota-Highlander-c24608)** - Average price: $16,640.00 - Good/great deal percentage: 37.8% - User rating: 4.76 / 5 - Total listings: 1,197 - **[2016 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2016-Toyota-Highlander-c25184)** - Average price: $17,934.00 - Good/great deal percentage: 37.6% - User rating: 4.63 / 5 - Total listings: 1,614 - **[2019 Toyota Highlander](https://www.cargurus.com/Cars/l-Used-2019-Toyota-Highlander-c27941)** - Average price: $23,223.00 - Good/great deal percentage: 35.2% - User rating: 4.57 / 5 - Total listings: 2,380 These recommendations are based on CarGurus' proprietary market data from March 9, 2026, CarGurus experts' opinions, and generative AI.

4.6 Overall rating

(691 reviews)

Customers say

Overall, the Toyota Highlander has built a strong reputation across its model years for reliability, comfort, and family-friendly features. Drivers appreciate its spacious interiors and smooth rides, often highlighting its impressive safety features as a key asset. Many also enjoy the performance and power of the engines. However, some common criticisms include a lack of advanced infotainment options in older models, tight third-row seating, and varying cargo space depending on configuration. Overall, the Highlander is seen as a dependable choice for families and an excellent value in the SUV market.

AI generated from the text of customer reviews.

What people say

cargo space comfort interior performance safety
Julie W
5.0
Reviewed a 2021 Toyota Highlander on Jul 20, 2024

I loved my Highlander. I give my 2021 Toyota Highlander a 100 out of 10 on its safety. My car was a limited and it had most bells and whistles which I loved but what I loved most was that we all walked away from a collision where we were traveling 40 miles an hour and thanks to the safety design , we’re here.

Melissa C
5.0
Reviewed a 2021 Toyota Highlander on May 05, 2024

Toyota knocked it out of the park again with this 2021 Highlander Platinum. Luxurious quiet ride Lexus feel like. Very happy with this purchase.

Emmanuel S
5.0
Reviewed a 2022 Toyota Highlander on Apr 18, 2024

The car is great with very nice features. It is a good value in terms of price and nothing is missing. It is a good looking car

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

James S
4.0
Reviewed a 2008 Toyota Highlander on Jul 16, 2024

We own 2 of these. One is the limited and the other is the all wheel drive. Over 150,000 on each and really just general maintenance issues so far with each. The clear coat is peeling and fading on the rear valance of each and the shocks and struts need to be replaced at this age. We have taken our limited everywhere including Texas, Colorado, North Carolina, Maryland, West Virginia, and more. Very good for families or dog owners and flexible with the third row seating. No major issues with either one so far!

Toyota Highlander FAQs

How much does the Toyota Highlander cost in Windsor, CT?

The average Toyota Highlander costs about $27,181.60. The average price has decreased by -5.6% since last year. The 588 for sale near Windsor, CT on CarGurus, range from $2,999 to $50,998 in price.

How many Toyota Highlander vehicles in Windsor, CT have no reported accidents or damage?

588 out of 588 for sale near Windsor, CT have no reported accidents or damage.

What fuel types are available?

Gasoline engines are available.

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