When you start looking really depends on how wide a net you intend to cast, and what your priorities you have in finding a location and home that works for you. For example, if you know Dover is a top choice, well, there's only 3 homes on the market in your price range, so it won't take very long to analyze that particular component of your decision! (Dover is very small and generally considered expensive, relative to MA prices). Some folks when the relocate look over a much wider area, and it takes time to whittle it down to a set of towns that have the features, commute, and home in their available budget. There's no right way to do it, there are many suitable locations in MA for each need and desire of the people involved.
Matt Heisler is a real-estate professional and owner of Heisler & Mattson Properties. He has been selling residential real-estate for over 10 years. He has given several talks on real estate, including presentations on first-time buyer tips & tricks, and profiting in real estate investing in Massachusetts. As a Vanderbilt University alumnus, he is proud to serve the communities of Natick, Framingham, Medfield, Millis, Holliston, Hopkinton, Southborough, Westborough, Northborough, Grafton, Marlborough, Shrewsbury, Worcester, Milford, Charlton, Northbridge, Sutton, Hudson, Sudbury, Clinton, Boylston, and West Boylston. His company website can be found at http://www.bjheisler.com,
and his Metrowest Blog can be read at http://HomeSellingInMass.net.
*All information is posted in good faith and is assumed to be reliable, but may rely on third party information sources.