OttoQuest
DATA NOV 11, 2026Pro ✦Sign in

Boston, MA · 50-mile radius

Used Toyota Highlander deals near Boston, MA

The median asking price is $28,900 across 587 used vehicles within 50 miles of Boston, MA. 138 are priced 5–30% below OttoQuest’s estimate for a comparable car.

Inventory checked over 7 days ending · Latest sighting

Browse matching inventory
Median asking price
$28,900
Middle half of asking prices
$19,458 – $37,000
First seen in the past 7 days
174

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Featured listings near Boston, MA. Pins mark approximate areas.

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Best deals near Boston, MA

Ranked by how far each asking price is below its own estimated value.

  1. 2010 Toyota Highlander Limited

    Holden, MA · 142,500 mi

    57 comparable cars · History unreported

    $8,449▼ 30% belowEst. $11,988
  2. 2009 Toyota Highlander Sport

    Dorchester, MA · 108,147 mi

    15 comparable cars

    $7,500▼ 29% belowEst. $10,504
  3. 2010 Toyota Highlander Hybrid Base

    Swansea, MA · 211,006 mi

    8 comparable cars · Accident reported

    $4,500▼ 27% belowEst. $6,166
  4. 2012 Toyota Highlander Hybrid Base

    Burlington, MA · 155,435 mi

    8 comparable cars

    $8,995▼ 25% belowEst. $11,908
  5. 2012 Toyota Highlander Limited

    Lawrence, MA · 185,566 mi

    121 comparable cars · History unreported

    $8,900▼ 21% belowEst. $11,274
  6. 2013 Toyota Highlander Limited

    Canton, MA · 171,837 mi

    175 comparable cars

    $9,488▼ 21% belowEst. $11,977
Browse below-market matches →

Recently spotted near Boston, MA

Matching cars we first saw in the past 7 days, newest sightings first.

  1. 2005 Toyota Highlander Base

    Auburn, NH · 141,308 mi

    First seen

    $5,995
  2. 2019 Toyota Highlander Limited

    Westborough, MA · 63,795 mi

    First seen

    $31,998
  3. 2022 Toyota Highlander XLE

    East Providence, RI · 47,300 mi

    First seen

    $33,995
  4. 2013 Toyota Highlander SE

    Marlborough, MA · 165,990 mi

    First seen

    $9,990
  5. 2021 Toyota Highlander XLE

    Nashua, NH · 50,816 mi

    First seen

    $34,095

Asking prices by model year

The most listed model years in this search. Mileage helps explain some of the difference in asking prices.

YearCarsMedian askMedian miles
202548$43,00024,461
202459$38,67936,451
202376$36,27046,576
202247$33,49561,550
202173$29,46084,126
201956$23,63794,891

Other used cars near Boston, MA

Used SUVs33,653Used SUVs up to $25,00016,223Used Toyota RAV41,534Used Honda CR-V1,475Used Ford F-1501,298Used Jeep Grand Cherokee1,238Used Jeep Wrangler1,146Used Chevrolet Silverado 15001,041Used Nissan Rogue998Used Subaru Forester997Used Honda Civic899Used Honda Accord885Used Ram 1500853Used Toyota Corolla840

Used Toyota Highlander in other cities

New York, NY722Washington, DC635Los Angeles, CA480Baltimore, MD431Chicago, IL415Fort Worth, TX398Philadelphia, PA385Minneapolis, MN385Dallas, TX380Atlanta, GA378Houston, TX353Seattle, WA323Portland, OR288Denver, CO281

How these numbers are calculated

What do the prices represent?

These are advertised asking prices for used and certified pre-owned vehicles, before taxes and registration. We use the lowest qualifying asking price per vehicle within 50 straight-line miles of the city center. The middle half is the range from the 25th to the 75th percentile. The median is a benchmark for this search; trim, mileage and condition affect what an individual car is worth.

What qualifies as a deal?

The price has to be 5–30% below our estimate, based on at least eight comparables for the same trim and model year. The estimate accounts for mileage where available, reported history and state. We leave out known modified cars from the deal ranking and exclude reported title issues from this search. Missing history doesn’t mean a car is clean. Confirm availability, vehicle history and the out-the-door price before visiting.

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