Used 2019 Toyota Highlander for Sale near Boston, MA
258 results
CarGurus Analysis:
2019 Toyota Highlander
With 240 currently listed for sale near Boston, MA and an average price of $24,974.00, 33.3% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.76 / 5 stars.
85.4% of 2019 Highlander models on CarGurus are accident free.
CarGurus Analysis: 2019 Toyota Highlander
Summary
With 240 currently listed for sale near Boston, MA and an average price of $24,974.00, 33.3% of 2019 Toyota Highlanders for sale on CarGurus are rated as good or great deals.
Favorably reviewed: Owners rated the 2019 Toyota Highlander 4.76 / 5 stars.
85.4% of 2019 Highlander models on CarGurus are accident free.
Why it stands out
The 2019 Toyota Highlander continues to impress as a reliable and spacious midsize SUV, favored by families for its comfort and safety features. Its powerful engine performance, combined with a well-appointed interior, provides a balanced driving experience. While some critics note that the Highlander's driving dynamics might not be thrilling, the vehicle's build quality, spacious cabin, and reputation for reliability offer significant appeal for buyers prioritizing longevity and safety over sporty handling. Moreover, its accident-free record enhances its standing as a practical choice in the used SUV market, making it an excellent option for those seeking a dependable family vehicle.
Other model years to consider
- Average price: $41,406.00
- Good/great deal percentage: 59.1%
- User rating: 5 / 5
- Total listings: 225
- Average price: $38,137.00
- Good/great deal percentage: 64.3%
- User rating: 4.75 / 5
- Total listings: 252
- Average price: $32,396.00
- Good/great deal percentage: 51.2%
- User rating: 4.86 / 5
- Total listings: 246
This analysis is based on CarGurus' proprietary market data from May 19, 2026, CarGurus experts' opinions, and generative AI.
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4.8 Overall rating
Filter by rating
Simone P
Reviewed a 2019 Toyota SE FWD on Aug 10, 2025
I just purchased a pre-owner Toyota Highlander. I picked the 2019 model because it is the last model year that had the rear window that opened independently from the lift gate. I missed that feature in my last two Honda CRV’s because the older (gen 1 &2) Honda CRV’s used to have that feature too. Both the CRV and Highlander have similar features and are both reliable and wonderful cars, which will last a long time. I just needed a larger car for my current needs. The Honda did get better gas mileage than the Toyota, but it was also a smaller SUV. I have owned different Honda CR-Vs for the last 30 years, and have been very happy with them. This is my first Toyota. The Highlander is very comfortable and roomy. My daughter really likes the captain’s seats in the back. I am very happy with the Highlander and plan to have it for many years.
Anonymous
Reviewed a 2019 Toyota Highlander on Sep 3, 2024
great combination of reliability, function and features and price. Has more than enough bells and whistles with great driveability and comfort
Dennis G
Reviewed a 2019 Toyota Limited AWD on Mar 27, 2025
Comfortable, strong and stylish. Plenty of room for wife's wheel chair, her and myself along with what ever else we need to transport. Did have a problem starting once after sitting 3 weeks unproven. Small portable starter was very handy, started right up. No issues since. Lot of safety reminders, clearance between you and car in front of you in cruse control, out of lane warning. Wish it had digital speed display. Nav works well. I have SiriusXM radio, killer sound.
Suzanne M
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 .
2019 Toyota Highlander Trims
| Trim type | MSRP |
|---|---|
| Limited FWD | $42,930 |
| Limited Platinum AWD | $47,510 |
| LE AWD | $35,340 |
| SE AWD | $42,400 |
| Limited AWD | $44,390 |
| LE FWD | $33,880 |
| XLE FWD | $39,720 |
| XLE AWD | $41,180 |
2019 Toyota Highlander Price Trends
CarGurus tracks the prices of millions of used car listings every year. See how the average price of 2019 Toyota Highlander prices has changed over time.
See more price trends2019 Toyota Highlander Pricing Analysis: Boston, MA Market Report
Pricing by Nearby Locations
Market Area: Boston, MA
Key Insights
- Groton, MA Offers the Best Price: With an average price of $25,241, Groton provides the most competitive pricing among the nearby cities.
- Highest Prices in Plymouth: Plymouth, MA ($25,885) shows the highest average price, indicating potential demand or lower inventory in that market.
- Stable Pricing Across Locations: Despite varying prices, inventory levels across markets like Worcester (262 listings) and Groton (259 listings) suggest a relatively stable market with consistent options.
City-Level Pricing
| City | Total Listings | Avg Price |
|---|---|---|
| Groton, MA | 259 | $25,241 |
| Plymouth, MA | 213 | $25,885 |
| Worcester, MA | 262 | $24,778 |
| Providence, RI | 226 | $24,774 |
| Manchester, NH | 228 | $24,952 |
| Portsmouth, NH | 205 | $24,768 |
| New Bedford, MA | 190 | $24,584 |
| Chicopee, MA | 220 | $23,776 |
| Brattleboro, VT | 181 | $24,698 |
| Hartford, CT | 201 | $23,687 |
Pricing by Trim Packages
Key Insights
- XLE AWD is the Most Available Trim: With 284 listings, the XLE AWD trim dominates inventory, indicating strong market preference for this all-wheel-drive option.
- Price Variation Among Trims: The Limited AWD trim at $44,390 MSRP positions itself as a significant premium option, creating about a 7.7% markup compared to the next most expensive trim, XLE AWD.
- Variety of Drivetrain Options: The split between AWD and FWD trims demonstrates diverse consumer needs, though AWD remains a popular choice for families needing versatility.
Trim-Level Details
| Trim | Listings | MSRP | Drivetrain | Engine |
|---|---|---|---|---|
| XLE AWD | 284 | $41,180 | AWD | 3.5L 295 hp V6 |
| Limited AWD | 105 | $44,390 | AWD | 3.5L 295 hp V6 |
| XLE FWD | 38 | $39,720 | FWD | 3.5L 295 hp V6 |
| LE AWD | 93 | $35,340 | AWD | 3.5L 295 hp V6 |
| LE FWD | 49 | $33,880 | FWD | 3.5L 295 hp V6 |
| Limited FWD | 17 | $42,930 | FWD | 3.5L 295 hp V6 |
| SE AWD | 46 | $42,400 | AWD | 3.5L 295 hp V6 |
| Limited Platinum AWD | 30 | $47,510 | AWD | 3.5L 295 hp V6 |
Pricing Analysis by Model Year
Key Insights
- 2026 Model at Premium Prices: The latest model (2026) lists for an average of $51,792, which is approximately 12.9% higher than its MSRP, reflecting strong demand or features.
- Depreciation Over Time: The 2018 Highlander has seen a downward trend with an average price of $22,676, indicating about a 27.5% drop from MSRP.
- Moderate Depreciation in Recent Years: The 2021 model remains competitive at $32,594, representing a modest 7.6% drop from its original MSRP, which suggests it retains value relative to older models.
Model Year Pricing
| Model Year | Original MSRP | Avg Price | Price vs MSRP |
|---|---|---|---|
| 2026 Toyota Highlander | $45,870 | $51,792 | +12.9% |
| 2025 Toyota Highlander | $40,320 | $44,242 | +9.5% |
| 2024 Toyota Highlander | $39,270 | $41,022 | +4.5% |
| 2023 Toyota Highlander | $36,620 | $38,106 | +4.0% |
| 2022 Toyota Highlander | $35,855 | $34,278 | -4.4% |
| 2021 Toyota Highlander | $35,085 | $32,594 | -7.6% |
| 2020 Toyota Highlander | $34,600 | $28,292 | -18.3% |
| 2019 Toyota Highlander | $32,230 | $22,676 | -29.6% |
| 2018 Toyota Highlander | $31,630 | $22,676 | -28.3% |
| 2017 Toyota Highlander | $30,630 | $19,707 | -35.8% |
| 2016 Toyota Highlander | $30,490 | $17,779 | -41.7% |
| 2015 Toyota Highlander | $29,765 | $17,431 | -41.4% |
These recommendations are based on CarGurus' proprietary market data from May 21, 2026, CarGurus experts' opinions, and generative AI.
