Used 2014 Toyota Highlander for Sale nearChicago, IL

How much does the 2014 Toyota Highlander cost?

Prices have softened 2.30% compared to this time last year, making it a favorable time to shop this model year.

There are 1,223 listings available, which gives you a solid amount of inventory to compare before you buy.

Is the 2014 Toyota Highlander a good car?

Yes — the 2014 Toyota Highlander earns a 4.78/5 user rating and an 8.67/10 expert rating. The standout strength is Safety at 10/10.

Owners consistently praise its reliability, comfort, and value for money, and they also like the spacious interior and useful features. That lines up well with its role as a practical family crossover that still brings some style and driving enjoyment to everyday use. If you want a vehicle that can handle school runs, errands, and weekend trips without feeling plain, this model year fits that brief well.

The market also shows 32.4% good or great deals, which suggests there are worthwhile opportunities if you shop carefully.

Is the 2014 Toyota Highlander reliable?

Owners rate it 4.78/5, a strong signal of long-term satisfaction.

The owner feedback repeatedly points to reliability, and the review summary also highlights a dependable, trouble-free ownership experience with strong value over the long term. On the road, the expert evaluation reinforces that impression by describing the Highlander as a capable, competent crossover that feels well suited to everyday use and longer-term family duty. The cost-effectiveness notes also emphasize that it delivers a lot of content for the price.

For used buyers, the main long-term ownership risk is less about the core vehicle and more about finding one that has been maintained well and not worn down by heavy family use.

What should I look for when buying a used 2014 Toyota Highlander?

At 57.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.

You should start with a vehicle history report and then prioritize a thorough pre-purchase inspection, especially if the listing price looks unusually attractive. Focus on condition details that matter in a family crossover: interior wear, seat comfort, electronics, and signs of hard use. If you’re comparing multiple listings, the cleanest example with the best maintenance history is usually the smarter buy.

Key things to evaluate:

• Trim level: The LE trim brings standard seating for 8, a 6.1-inch touchscreen, a backup camera, Bluetooth hands-free calling, and lots of storage space. LE Plus adds three-zone climate control with rear climate toggles, a leather-wrapped steering wheel and shifter, and SofTex leatherette seating. XLE adds navigation, leather seating, and a detailed color digital display in the instrument panel. Limited adds 19-inch wheels, a JBL audio system, and upgraded safety tech like blind-spot monitoring. The LE Plus is the best-value trim if you want a noticeable comfort upgrade without jumping all the way to the top.
• Powertrain: The base LE uses a 185-hp 2.7-liter inline 4-cylinder, but the 3.5-liter V6 is the stronger choice and is optional on LE and standard on LE Plus and above. The V6 makes 270 hp and pairs with a 6-speed automatic transmission. Front-wheel-drive V6 trims are rated at 19 mpg city and 25 highway, while I4 FWD trims are rated at 20/25.
• Safety package: The Highlander comes standard with a backup camera, tire pressure monitoring system, and a full array of advanced front and side impact airbags. With the available pre-collision system, it is a 2014 Top Safety Pick Plus award winner. Available driver-assistance features include lane-departure warning, automatic high beams, blind-spot monitoring, and rear cross-traffic alert. The Limited trim adds upgraded safety tech like blind-spot monitoring.
• Infotainment: The Highlander uses Entune, a multimedia touchscreen interface with apps such as Pandora, Yelp, and Bing. The base setup includes a 6.1-inch touchscreen, and navigation is available on higher trims. The system does not give navigation a dedicated dash button, so you access it through the app page.
• Fuel efficiency: The V6 with front-wheel drive is rated at 19 mpg city and 25 highway, while the I4 with front-wheel drive is rated at 20 mpg city and 25 highway. The AWD V6 test trim was listed at 18 mpg city and 24 highway.

Which 2014 Toyota Highlander trim should I buy?

The 2014 Toyota Highlander is offered in 4 trim levels: LE, LE Plus, XLE, and Limited.

Here's the short version:

• LE: This is the entry point, and it gives you the essentials: 8-passenger seating, a 6.1-inch touchscreen, a backup camera, Bluetooth hands-free calling, and plenty of storage. It makes sense if you want the lowest starting price and can live without the nicer cabin upgrades.
• LE Plus: This is the best-value trim for many shoppers because it adds three-zone climate control with rear climate toggles, a leather-wrapped steering wheel and shifter, and SofTex leatherette seating. It’s the sweet spot if you want a more comfortable family SUV without paying for the upper trims.
• XLE: This trim adds navigation, leather seating, and a detailed color digital display in the instrument panel. Choose it if you want a more upscale feel and are willing to pay for convenience and cabin polish.
• Limited: This is the most feature-rich version, with 19-inch wheels, a JBL audio system, and upgraded safety tech like blind-spot monitoring. It suits you if you want the most equipment and are willing to pay for it.

The safety package is strongest when the available pre-collision system is equipped, since that configuration earns the Top Safety Pick Plus recognition.

Is now a good time to buy a used 2014 Toyota Highlander?

This is a moderate market, so you can be selective without expecting a fire-sale environment.

• Deal availability: 32.4% of listings are priced as good or great deals.
• Inventory: There are 1,223 listings available.
• Price trend: Prices have softened 2.30% compared with last year.
• Clean inventory: 57.5% of listings are accident-free.

If you find a listing below $14,943, that's toward the low end of the year-round range and worth acting on quickly.

What is the 2014 Toyota Highlander's resale value?

The current average of $15,576 sits slightly below last year's $15,943.

That softer pricing trend suggests the market has become a bit more buyer-friendly, which can work against sellers who wait too long. If you’re planning to resell later, the current direction implies you may not see rapid appreciation, so condition and mileage will matter a lot when it’s time to list. Well-kept examples should still hold up better than average because shoppers continue to value this model’s practicality and reputation.

Vehicles with strong owner satisfaction ratings, like this model year's 4.78/5, tend to retain buyer demand, which supports resale value over time.

Is the 2014 Toyota Highlander safe?

The 2014 Toyota Highlander earns a Top Safety Pick Plus award from IIHS when equipped with the available pre-collision system.

It earns a 10/10 safety score from our experts.

The standard safety equipment includes a backup camera, tire pressure monitoring system, and a full array of advanced front and side impact airbags. Available driver-assistance features include lane-departure warning, automatic high beams, blind-spot monitoring, and rear cross-traffic alert. The Limited trim adds upgraded safety tech like blind-spot monitoring, and the pre-collision system is the key feature tied to the strongest safety recognition.

Should I buy a 2014 Toyota Highlander or consider a different year?

If you're weighing the 2014 against nearby model years, here's how to think about it:

Choose the 2014 if:

• 32.4% of listings are priced as good or great deals.
• At 57.5% accident-free, a meaningful share of listings has prior incidents — history verification is especially important.
• Price trend: Prices have softened 2.30% compared with last year.
• Owners rate it 4.78/5 — a strong satisfaction signal.
• The 2014 stands out for bringing a more youthful design, strong everyday usefulness, and a Top Safety Pick Plus configuration when equipped with the available pre-collision system.

The bottom line: The 2014 is a smart choice if you want a family crossover with strong owner satisfaction, good safety credentials, and a market that still offers some room to shop selectively. If you’re especially price-sensitive, focus on the cleanest, best-maintained listing you can find rather than chasing the cheapest one, since accident history and condition matter a lot in this market.

These recommendations are based on CarGurus' proprietary market data from September 29, 2026, CarGurus experts' opinions, and generative AI.