Best Jeep Cherokee Sport Year to Buy
There is no single best Jeep Cherokee Sport year: the right one depends on your budget and what you want from the car. Across 135 verified sales, the 2001 is the most affordable at $11,238 and trades most often (60 verified sales).
Data: DriveIndex. 4 model years with at least 10 verified sales each, latest sale Sep 25, 2026. Methodology
Ranked across the 4 years with at least 10 verified sales. Years with fewer are in the table below but too thin to rank.
Jeep Cherokee Sport Value by Model Year
| Year | Value | Vs. original MSRP | Verified sales | For sale |
|---|---|---|---|---|
| 2001 Cherokee Sport | $11,238 | — | 60 | — |
| 2000 Cherokee Sport | $13,131No sale since Jan 2026 | — | 21 | — |
| 1999 Cherokee Sport | $16,605 | — | 18 | — |
| 1998 Cherokee Sport | $22,189No sale since Feb 2026 | — | 14 | — |
| 1997 Cherokee Sport | $21,012No sale since Apr 2026 | — | 9 · too few to rank | — |
| 1996 Cherokee Sport | $20,457No sale since Aug 2025 | — | 5 · too few to rank | — |
| 1995 Cherokee Sport | $13,614No sale since May 2025 | — | 4 · too few to rank | — |
| 1994 Cherokee Sport | $16,906 | — | 4 · too few to rank | — |
Value is DriveIndex's market value for each year, from verified sales. “Vs. original MSRP” compares it with the sticker price when new, not adjusted for inflation: 100% means it is worth exactly what it cost. Years with fewer than 10 verified sales are listed but not ranked.
Which Cherokee Sport year is appreciating?
The table shows what each year is worth. Pro adds the direction: the live Value Signal for every year, how confident it is, a 1–5 year projection, and every sold price behind it. Collector adds the best months to buy and an estimated market-bottom date.
Or see the best months to buy with Collector ($39.99/month), or start with a free account.
Best Jeep Cherokee Sport Year: Frequently Asked Questions
What is the best Jeep Cherokee Sport year to buy?
There is no single best Jeep Cherokee Sport year: the right one depends on your budget and what you want from the car. Across 135 verified sales, the 2001 is the most affordable at $11,238 and trades most often (60 verified sales). The table on this page lists every model year with its market value, its value against its original MSRP and how many have sold.
Which Jeep Cherokee Sport year is the cheapest?
The 2001 Jeep Cherokee Sport is the most affordable year with enough verified sales to compare, currently valued at $11,238. The most valuable is the 1998, at $22,189. No sale since Feb 7, 2026, so the 1998's value may not reflect today's market.
How much is a Jeep Cherokee Sport worth?
Depending on the model year, a Jeep Cherokee Sport is worth from $11,238 to $22,189 today, based on verified sales. Mileage, condition and options move any single car's price; each year's page shows its recent sales.
Which Jeep Cherokee Sport year is appreciating?
This page shows what each year is worth and how that compares with its original price. Whether each year is appreciating, stable or depreciating is DriveIndex's Value Signal, which Pro members see for every year along with a 1–5 year projection.