I went to school at Northeastern and so spent plenty of time in that neighborhood. We actually looked at buying in Jamaica Plain because of the price difference. Ultimately we didn't because our kids had grown roots in Brookline and the Jamaica Way was too much of a barrier between the neighborhoods.

I think the biggest difference in the price between the two neighborhoods is the schools. Once you cross over the border (either into JP, or the less segmented allston) the prices drop. Brookline's got well-regarded schools (though they've been coasting), whereas Boston is a mixed bag with a lottery system.