If the property has already been on the market starting at $275k then that price has been well tested in the market and has apparently been found wanting. I’d venture to say the real comps for this house probably aren’t the $290k sales you are referring to.
If the market value in 1999 was $215k and the current list on this house is $260k that represents an annual increase of ~3%, just slightly ahead of the annual rate of inflation. This is definitely not indicative of what we would call a bubble market. I don’t think you have to worry about this property losing a ton of value over the next few years.
That is, beyond whatever local economic conditions could occur to decimate local employment. Is this a town that’s overly dependent on one or two companies in a manufacturing industry? If not then it almost doesn’t matter whether you offer $240k or $260k. The spread between them is only 8%; that’s practically within a reasonable margin of error.
