Price Range: $500-$3000
The earliest XR250Rs were basically a 500 chassis and a shrunken-displacement 500 engine. Not a shrunken engine, so the bikes ended up with the weight of a 500 and the power of a 200; Honda finally got the right equation in 1986. The engine was a four-valve configuration with an oil cooler to better control engine heat. The bike got a major upgrade in 1990 when the drum rear brake was swapped for a disc and the fork gained cartridge-type damping. While the bike didn't really feel much different, the 1996 to 2005 models were new with a similar but not identical engine. The frame and ergonomic package was more like the XR400R, and the 41mm cartridge fork was of the low-underhang-type design like the 43mm units on the XR400.
Buyer Beware
The XR has a deserved reputation for great reliability, but you certainly want a bike that had regular clean oil and air filters. Without those two things, even the XR can and will break.
Some of these bikes were converted (by owners) for dual-sport, and those plated models will be the ones with the highest prices.
All years were easy starting and pretty mindless to maintain. These bikes appealed to people who didn't want to work on them, so many are thrashed. Stay away from smokers or those that have been modded to higher compression.
Commonsense Mods
Make sure the engine is fresh mechanically, and that there isn't a radical cam or stiff valve springs installed, though 280cc kits are common and, as long as they aren't high-compression, they work pretty well. These aren't really race bikes today, though many riders (including Jimmy Lewis) won ISDE gold medals on them.
The engine doesn't need a loud pipe, so look for a quiet one. If you have the stock muffler, the insert from an ATC 200X offers a good sound/power compromise.
Uni Filter makes a larger filter and cage for dusty areas.
The '96 to '05 suspension internals are vastly superior to earlier ones, and the rear disc bikes are all more desirable than the rear drum bikes. Fortunately, all of the stock suspension is fine for trail use.
An aluminum handlebar is a wise replacement for the stock steel bar
Target Rider
No matter what the year, a clean example of the XR250R is a simple and reliable trailbike that is great for short or learning riders. It weighs 251 pounds with no gas, so the weight and taller seat height limit it to slightly taller riders than the XR200. For comparison, the modern 250X weighs 243, has 33 percent more power and has a much taller seat height. The air-cooled XR doesn't have finicky carburetion, and it kickstarts fairly easily and consistently.