1999 Jeep Cherokee Sport Market Value & Price History
The 1999 Jeep Cherokee Sport has a current market value of $16,605 as of Oct 9, 2026, based on 18 verified auction sales tracked by DriveIndex, with half of the verified USD sales since 2022 between $12,750 and $20,550. Based on US sales through Aug 14, 2026. 3 have sold in the past 12 months. The median sale price is up 3.3% over the past 12 months versus one to three years ago.
Data: DriveIndex. 18 verified auction sales for the 1999 Jeep Cherokee Sport, latest sale Aug 14, 2026. Value as of Oct 9, 2026. Methodology
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See the Cherokee Sport's Value Signal with Pro →1999 Jeep Cherokee Sport Price History
The median 1999 Jeep Cherokee Sport sold for $14,625 in 2024, against $20,550 in 2023. Each row is the median of the verified sales recorded in that calendar year, so it moves with the mix of mileages and options that came to market as well as with the market itself.
| Year | Median sale | Sales |
|---|---|---|
| 2024 | $14,625 | 6 |
| 2023 | $20,550 | 7 |
Years with fewer than three verified USD sales are omitted — a one-sale “median” is a single car, not a market.
Recent 1999 Jeep Cherokee Sport Auction Results
| Sold | Price | Mileage | Gearbox |
|---|---|---|---|
| Aug 14, 2026 | $38,000 | 24,000 mi | Automatic |
| May 23, 2026 | $18,250 | 81,000 mi | Automatic |
| Oct 17, 2025 | $12,250 | 91,000 mi | Automatic |
| Oct 9, 2025 | $11,500 | 122,000 mi | — |
| Sep 16, 2024 | $12,750 | 94,000 mi | Automatic |
| Jul 8, 2024 | $18,850 | 66,000 mi | Automatic |
| Jul 6, 2024 | $10,250 | 189,000 mi | — |
| Mar 28, 2024 | $10,250 | 154,000 mi | Automatic |
| Jan 6, 2024 | $16,500 | 145,000 mi | Automatic |
| Jan 4, 2024 | $19,250 | 76,000 mi | — |
| Dec 3, 2023 | $23,250 | 32,000 mi | Automatic |
| Nov 21, 2023 | $21,900 | 70,000 mi | Automatic |
| Oct 10, 2023 | $20,277 | 37,000 mi | Automatic |
| Apr 28, 2023 | $20,550 | 46,000 mi | Automatic |
| Apr 14, 2023 | $17,000 | 68,000 mi | Automatic |
Verified results from the world's leading collector-car auction houses and marketplaces.
All Jeep Cherokee Sport auction results →See the full picture on the 1999 Jeep Cherokee Sport
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Jeep Cherokee Sport by Year
Which Cherokee Sport year should you buy? Every year compared →1999 Jeep Cherokee Sport: Frequently Asked Questions
How much is a 1999 Jeep Cherokee Sport worth?
A 1999 Jeep Cherokee Sport is worth approximately $16,605 as of Oct 9, 2026, based on 18 verified auction sales tracked by DriveIndex. Based on US sales through Aug 14, 2026. Half of all verified sales fall between $12,750 and $20,550; the full verified range is $10,250 to $38,000. Condition, mileage and options move an individual car within that band.
How many 1999 Jeep Cherokee Sport sell per year?
3 have sold at auction in the past 12 months. DriveIndex has tracked 18 1999 Jeep Cherokee Sport sales in total.
Are 1999 Jeep Cherokee Sport sale prices higher or lower than a year ago?
The median 1999 Jeep Cherokee Sport sale price is up 3.3% over the past 12 months versus one to three years ago, based on verified auction sales. That figure tracks the median of what actually sold, so it moves with the mix of mileages and options that came to market as well as with the market itself. The full Value Signal classification (appreciating, stable, bottomed, or depreciating) and its 1–5 year projection are part of DriveIndex Pro.
Where can I buy a 1999 Jeep Cherokee Sport?
DriveIndex tracks for-sale listings and auction results for the 1999 Jeep Cherokee Sport from the world's leading collector-car auction houses and marketplaces.
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