any reason why land with 2 houses could NOT be split?

[Kira Botkin]

I'm looking at a property that seems like a good deal for owner-occupant plus a renter - it has a nice 3 bedroom house on the street, and another 2 bedroom kind of odd looking house on the back half of the property. (not a big piece either.) Both houses have been rentals for some time. I am thinking, why not split off the back house and sell it individually? This is a good area and even condos are $150k+ and many houses are only 2 bedroom, so it wouldn't be hard to sell, especially if fixed up. My concern though is, it is listed for $259k for both houses, and they are easily worth $50k or more than that together, even if they look like crap on the inside. There might be some structural issues or something, but I am worried that there is something legal going on. So I am a little suspicious of the lower price, and, why the current owners haven't split the property already. The two houses are not touching or anything, and it's pretty common in the area to have carriage house apartments, so addresses that aren't actually on the street is also common (the second house does have its own house number, it isn't a 1/2 or anything.)

Can anyone think of any reasons that the current owners might NOT have wanted or been able to split this property in two and sell the houses individually? What should I ask of the agent when I go see this? Any other suggestions?